DK157189B - IN THE 6'-POSITION EVEN WITH ALKYL SUBSTITUTED N- (0-SUBSTITUTED-OXY-METHYL) -2'-TRIFLUORMETHYL-2-CHLOR ACETANILIDES AND HERBICIDE MIXTURES INCLUDING THESE - Google Patents

Description

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Opfindelsen angâr i 6-stillingen eventuelt med alkyl sub-stituerede N-(Q-substitueret-oxymethyl)-2-trifluormethyl-2-chloracetanilider med herbicid virkning.The invention relates in the 6-position optionally with alkyl substituted N- (Q-substituted-oxymethyl) -2-trifluoromethyl-2-chloroacetanilides with herbicidal activity.

Den kendte teknik omfatter talrige beskrivelser af 2-ha-5 logenacetanilider, der kan være usubstituerede elker sub- stituerede med mange forskellige substituenter pâ anilid-nitrogenatomet og/eller pâ anilidringen, herunder f.eks. alkyl-, alkoxy-, alkoxyalkyl-, halogenalkyl-'og halogen-radikaler.The prior art includes numerous descriptions of 2-halogen acetanilides which may be unsubstituted or substituted with many different substituents on the anilide nitrogen atom and / or on the anilide ring, including e.g. alkyl, alkoxy, alkoxyalkyl, haloalkyl, and halogen radicals.

10 Soin mëre relevant for forbindelserne ifolge opfindelsen, der er karakteriseret ved at hâve et alkyloxymethyl- el-ler alkoxyalkyloxymethyl- eller alkenyloxymethyl- eller alkynyloxymethyl-radikal pâ anilidnitrogenatomet, et trifluormethylradikal i en ortoposition og et methylra-15 dikal eller i specifikke tilfælde et ethylradikal eller hydrogen pâ den anden ortoposition, kan det anfores, at den kendte teknik, som er mest beslægtet med opfindelsen, synes at være belgisk patentskrift nn. 810 763. Den mest relevante beskrivelse i det belgiske patentskrift nr.Species relevant to the compounds of the invention characterized by having an alkyloxymethyl or alkoxyalkyloxymethyl or alkenyloxymethyl or alkynyloxymethyl radical on the anilide nitrogen atom, a trifluoromethyl radical in an orthopedic or a methyl radical or a methyl radical or hydrogen at the other orthoposition, it may be argued that the prior art most closely related to the invention appears to be Belgian patent nn. 810 763. The most relevant description in Belgian patent no.

20 810 763 er-de generiske beskrivelser af N-alkoxyethyl- eller alkyl-substituerede alkoxyethyl-2-chloracetanili-der, der kan være substitueret pâ anilidringen pâ orto-og metapositionerne med et eller flere radikaler, der kan vælges blandt et storre antal radikaler, herunder ha-25 logen, alkyl, alkoxy eller trifluormethyl (-CP^)-20 810 763 are the generic descriptions of N-alkoxyethyl or alkyl substituted alkoxyethyl 2-chloroacetanilides which may be substituted on the anilide ring at the ortho and metapositions by one or more radicals selectable from a greater number of radicals , including the halogen, alkyl, alkoxy or trifluoromethyl (-CP

Det kan især anfores, at listen af forbindelser i tabel II i belgisk patentskrift nr. 810763 omfatter forbindelser, der er substitueret med et -CF3~radikal i en orto-stilling uden nogen substituenter i den anden ortostil-30 ling (forbindelser nr. 37 - 48) og forbindelser, der har en -CF^-substitution i en metastilling med en orto-stilling usubstitueret og den anden ortostilling substitueret med et methoxyradikal (forbindelser nr. 22-25) eller et chloratom (forbindelser nr. 33 - 36). Der foreligger dog ingen specifik beskrivelse eller eks-In particular, it may be stated that the list of compounds in Table II of Belgian Patent Specification No. 810763 comprises compounds substituted with a -CF 3 radical in an ortho position without any substituents in the second ortho position (Compounds No. 37 - 48) and compounds having a -CF 2 substitution in a meta position having an ortho position unsubstituted and the other ortho position substituted by a methoxy radical (compounds Nos. 22-25) or a chlorine atom (compounds Nos. 33-36) . However, there is no specific description or excerpt.

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2 emplificerende forbindelser i de fra belgisk patentskrift nr. 810 763 kendte forbindelser pâ 2-halogenacetanilider, der er substitueret med et -CF^-radikal i en orttostilling og et methyl- eller ethylradikal i den anden ortostilling 5 sorti ved forbindelserne ifolge opfindelsen. Desuden er de fra belgisk patentskrift nr. 810 763 kendte forbindelser karakteriseret ved en alkoxyalkylgruppe, der er substitueret pâ anilidnitrogenatomet, hvorved alkylenmolekyldelen ' ikke mâ hâve under to carbonatomer mellem nitrogen- og 10 oxygenatomet i alkoxymolekyldelen. Derimod er forbindelserne ifolge opfindelsen yderligere partielt karakteriseret ved substitutionen pâ aniridnitrogenatomet af et alkoxymethylradikal. Betydningen af de ovenfor angivne sondringer mellem forbindelserne i belgisk patentskrift 15 nr. 810 763 og den foreliggende opfindelse vil blive ty-delig ved henvisning til de her angivne, komparative herbicide data, der tydeligt dokumenterer overlegenheden af forbindelserne ifolge opfindelsen hvad angâr enhedsakti-vitet, selektivitet, ukrudstkontrolspektrum og afgrode-20 sikkerhed.2 emplifying compounds in the compounds known from Belgian Patent No. 810,763 on 2-haloacetanilides substituted by a -CF 2 radical in one ortho position and a methyl or ethyl radical in the other ortho position 5 in the compounds of the invention. In addition, the compounds known from Belgian Patent No. 810,763 are characterized by an alkoxyalkyl group substituted on the anilide nitrogen atom, whereby the alkylene molecule moiety must not have under two carbon atoms between the nitrogen and oxygen atom of the alkoxy molecule moiety. In contrast, the compounds of the invention are further partially characterized by the substitution on the aniride nitrogen atom of an alkoxymethyl radical. The significance of the above distinctions between the compounds of Belgian Patent No. 15,108,763 to the present invention will be made clear by reference to the comparative herbicidal data disclosed herein which clearly demonstrates the superiority of the compounds according to the invention in terms of unit activity, selectivity, weed control spectrum and crop security.

Anden relevant kendt teknik, der er mindre beslægtet med opfindelsen end det ovenfor ang-ivne belgiske patentskrift nr. 810 763, omfatter US patentskrifter nr. 3 966 811 og 4 152 137, DE ansogning nr. 2 013 188 og sydafrikansk 25 patentskrift nr. 74/0767. Skont disse referencer indehol- der generiske beskrivelser af 2-halogenacetanilider, der blandt andre substituenter kan indeholde -CF-^substitu-tion pâ anilidringen, er den eneste beskrivelse af forbindelser af denne type i disse referencer at finde i det 30 angivne US patentskrift nr. 3 966 811 og sydafrikansk patentskrift nr. 74/0767. Selv dette taget i betragtning indeholder hverken US patetnskrift nr. 3 966 811 eller sydafrikansk patentskrift nr. 74/0767 en omtale af nogen forbindelser nted orto-CF^-substitution eller nogen spe-35 cifik angivelse af sâdanne forbindelser, der yderligere er substitueret i den anden ortostilling med et methyl- /Other relevant prior art less related to the invention than the aforementioned Belgian Patent Specification Nos. 810,763 include U.S. Patents Nos. 3,966,811 and 4,152,137, DE Application No. 2,013,188, and South African Patent Nos. 25,403. 74/0767. Although these references contain generic descriptions of 2-haloacetanilides which, among other substituents, may contain -CF- 3 substitution on the anilide ring, the only description of compounds of this type in these references is to be found in U.S. Pat. 3 966 811 and South African Patent Specification No. 74/0767. Even considering this, neither U.S. Patent Specification No. 3,966,811 nor South African Patent Specification No. 74/0767 contains any mention of any compounds including ortho-CF 2 substitution or any specific indication of such compounds further substituted in the second ortho position with a methyl /

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3 eller et ethylradikal; de eneste -CF^-substituerede for-bindelser, der er beskrevet i disse patentskrifter, er de meta-CF-j-substituerede forbindelser. Hertil kommer, at bâde US patentskrift nr. 3 966 811 og sydafrikansk patent-5 skrift nr. 74/0767 ligesom det belgiske patentskrift nr.3 or an ethyl radical; the only -CF 2 -substituted compounds described in these patents are the meta-CF-j-substituted compounds. In addition, both U.S. Patent No. 3,966,811 and South African Patent No. 5,774,767, as well as Belgian Pat.

810 763 kræver, at der skal være ikke under to carbonato-mer mellem anilidnitrogenet og oxygenet i alkoxymolekyl-delen, hvilket er et krav, der er beskrevet i aile de fo-regâende referencer, der repræsenterer kendt teknik, ined 10 undtagelse af det angivne US patentskrift nr. 4 152 137, der - som anfort - overhovedet ikke beskriver nogen -CF^-substituerede forbindelser.810 763 requires that there should be no less than two carbon atoms between the anilide nitrogen and the oxygen in the alkoxymolecule moiety, which is a requirement described in all of the prior art references representing prior art, except for the exception U.S. Patent No. 4,152,137, which - as noted - does not disclose any -CFF-substituted compounds at all.

Blandt de ovenfor angivne referencer, der angâr kendt teknik, beskriver kun det angivne belgiske patentskrift 15 nr. 810 763 og det sydafrikanske patentskrift nr.74/0767 nogle herbicide data, hvad angâr N-alkoxyalkyl-2-halogen-acetanilider med -CF^-substitution pâ anilidringen. Selv i dette tilfælde er denne beskrivelse vag, ubestemt og ufuldstændig. F.eks. beskriver det angivne belgiske pa-20 tentskrift nr. 810 763 begrænsede herbicide data for en -CF3~substitueret forbindelse, nemlig forbindelse nr. 37 (der er den sairane forbindelse som i eksempel 2), nemlig 2-trifluormethyl-N-(2'-methoxyethyl)-2-chloracetanilid.Among the prior art references cited above, only the Belgian Patent Specification 15 No. 810 763 and the South African Patent Specification No. 74/0767 disclose some herbicidal data with respect to N-alkoxyalkyl-2-haloacetanilides with -CF substitution on the anilide ring. Even in this case, this description is vague, indeterminate, and incomplete. Eg. Belgian Patent Specification No. 810,763 discloses limited herbicidal data for a -CF3-substituted compound, namely compound # 37 (which is the acid compound as in Example 2), namely 2-trifluoromethyl-N- (2 '). methoxyethyl) -2-chloroacetanilide.

I tabel 3 i det belgiske patentskrift nr. 810 763 er det 25 vist, at forbindelse nr. 37 odelægger eller pâ alvorlig mâde beskadiger visse uidentificerede forbindelser af "Cuperus", Setaria, Digitaria og Enchinochloa med liden beskadigelse af ukrudtene Avene fatua og en uidentifice-ret art af Lolium i visse afgroder. Mangelen af specifik 30 identitet af fem af de seks ukrudtsarter, der er under-sogt, udelukker en meningsfyldt evaluering af den herbicide effektivitet af den angivne forbindelse nr. 37.Table 3 of Belgian Patent Specification No. 810 763 shows that compound # 37 destroys or severely damages certain unidentified compounds of "Cuperus", Setaria, Digitaria and Enchinochloa with minor damage to the weeds Avene fatua and an unidentified -right species of Lolium in certain crops. The lack of specific identity of five of the six weed species investigated precludes a meaningful evaluation of the herbicidal efficacy of the indicated compound # 37.

Pâ lignende mâde beskriver det angivne sydafrikanske patentskrift nr. 74/0767 kun begrænsede herbicide data for 4Similarly, the disclosed South African Patent Specification No. 74/0767 discloses only limited herbicidal data for 4

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en -CF^-substitueret forbindelse, nemlig forbindelse nr.a -CF 2 -substituted compound, namely compound no.

78, dvs. 2,6-dimethyl-3-trifluormethyl-N-(2,-methoxy-ethyl)-N-2-chloracetanilid. De eneste herbicide data, der er beskrevet for forbindelse nr. 78, findes i eksem-5 pel 5, hvor forbindelse nr. 78 siges at udvise meget stærk vækstinhibering af fire arter af græsukrudt. Der er dog ikke angivet nogen laboratorie- eller markdata i det angivne sydafrikanske patentskrift nr. 74/0767 i forhold til effekten af forbindelse nr. 78 pâ nogen af-10 grode, eller om denne forbindelse udviser selektiv kon-trél af nogen ukrudt i nogen afgrode, hvorved enhver meningsfyldt evaluering af denne forbindelse baseret pâ sâdanne begrænsede data gores umulig. Selv om de ovenfor angivne, mest relevante referencer yderligere beskriver 15 herbicid aktivitet over for mange forskellige ukrudtsar-ter, beskriver de ikke nogen data for nogen -CF^-substi-tuerede N-alkoxy-alkylforbindelser, om hvilke det er pâ-vist, at de yderligere og/eller samtidigt i en eller fie-re afgroder udviser kontrol eller undertrykkelse af de 20 vanskeligt udryddelige flerârige ukrudt kvikgræs, gui og purpur "nutsedge" og et bredt spektrum af etârige ukrudts-arter, herunder sâdanne vanskeligt udryddelige, etârige græsukrudt som durra-kimplante, "shattercane", alexander-græs (Brachiaria plantaginea), panicum (Texas og vild 25 proso), rod ris og klogræs (Raoulgræs), mens de ogsâ kon-trollerer eller undertrykker andre skadelige flerârige og etârige ukrudt, f.eks. efterârs-panicum, "smartweed", hvidînelet gâsefod, kvinoa, rævehaler (f.eks. kæmperæve-hale og gui rævehale), fingeraks, hanespore, ipomoea, 30 flojlsblad, brodfro, portulak, hamp sesbania, tornet sida osv.78, i.e. 2,6-dimethyl-3-trifluoromethyl-N- (2-methoxy-ethyl) -N-2-chloroacetanilide. The only herbicidal data described for compound # 78 are found in Example 5, where compound # 78 is said to exhibit very strong growth inhibition of four grass weed species. However, no laboratory or field data is disclosed in the specified South African Patent Specification No. 74/0767 in relation to the effect of compound # 78 on any of the crops, or whether this compound exhibits selective control of any weeds in any crops, making any meaningful evaluation of this compound based on such limited data impossible. Although the above most relevant references further describe 15 herbicidal activity against many different weed species, they do not disclose any data for any -CF 2 -substituted N-alkoxy-alkyl compounds, as shown, that they further and / or simultaneously in one or four crops exhibit control or suppression of the 20 difficult extinct perennial weeds, gui and purple nutsedge, and a wide range of annual weeds, including such difficult extinct annual grasses such as durra seedling, "shattercane", alexander grass (Brachiaria plantaginea), panicum (Texas and wild 25 pros), root rice and clover grass (Raoul grass), while also controlling or suppressing other perennial and annual weeds, f .g. autumn panic, "smartweed", white goose's foot, quinoa, fox's tail (eg fox's tail and gui fox's tail), thimble, male's groove, ipomoea, 30 leaflets, embroidery, portulak, hemp sesbania, thorny side, etc.

En .i hoj grad anvendelig og onskværdig egenskab af herbi-cider er evnen til at bibeholde ukrudtskontrol over et udstrakt tidsrum, j.o længere, jo bedre, i hver hostsæson..A highly applicable and undesirable property of herbicides is the ability to maintain weed control over an extended period of time, the longer, the better, in each host season.

35 I forbindelse med mange kendte herbicider er ukrudtskon-35 In connection with many known herbicides, weed control

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5 trol kun tilstrækkelig i 2 eller 3 uger, eller i visse tilfælde med overlegne egenskaber mâske op til 4-6 uger, fer kemikaliet mister sine effektive phytotoxiske egenskaber. I overensstemmelse dermed er en ulempe ved 5 de fleste kendte herbicider deres relativt korte levetid i jordbunden.5 trol only sufficiently for 2 or 3 weeks, or in some cases with superior properties may last up to 4-6 weeks, the chemical loses its effective phytotoxic properties. Accordingly, a disadvantage of most known herbicides is their relatively short life in the soil.

En anden ulempe ved noglë kendte herbicider, der i nogen grad har relation til levetiden i jorden under normale meteorologiske betingelser, er deres folsomhed overfor 10 udludning i jorden, og som folge deraf mangelen pâ sta-biliteten af ukrudtskontrol under kraftige regnskyl, der inaktiverer mange herbicider.Another disadvantage of some well-known herbicides that are somewhat related to the life of the soil under normal meteorological conditions is their sensitivity to leaching into the soil, and as a result the lack of stability of weed control during heavy rains which inactivates many herbicides.

En yderligere ulempe ved mange kendte herbicider er be-grænsningen af deres anvendelse i specificerede typer af 15 jord, dvs. mens nogle herbicider er effektive i jord med smâ mængder af organisk materiale, er de ikke effektive i andre typer af jord, der indeholder meget organisk materiale eller vice versa. Det er derfor fordelagtigt, at et herbicid er anvendeligt i aile typer af jord, gâende 20 fra lette organiske jorder til tungt 1er og dyregodning.A further disadvantage of many known herbicides is the limitation of their use in specified types of soil, ie. while some herbicides are effective in soils with small amounts of organic matter, they are not effective in other types of soil that contain a lot of organic matter or vice versa. It is therefore advantageous for a herbicide to be useful in all types of soil, ranging from 20 light organic soils to heavy soils and animal fertilizers.

Endnu en ulempe ved mange kendte herbicider er begræns-ningen til en særlig effektiv pâforingsmetode, nemlig ved pâforing pâ overfladen for spiring ellier ved inkorpore-ring i jorden for og/eller efter sâning. Det er i hoj 25 grad onskværdigt at være i stand til at pâfore et herbicid i form af en vilkârlig pâforingsmetode, uanset om denne omfatter overfladepâforing eller inkorporering i jorden.Yet another disadvantage of many known herbicides is the limitation to a particularly effective method of application, namely by application on the surface of germinating ellis by incorporation into the soil before and / or after sowing. It is highly desirable to be able to apply a herbicide in the form of any method of application, whether it involves surface application or incorporation into the soil.

Slutteligt er en ulempe ved visse herbicider, at det er 30 nodvendigt at gore brug af og bibeholde specielle hând-teringsmetoder pâ grund af den toxiske natur deraf. Et yderligere onske er sâledes, at herbicidet er sikkert at hândtere.Finally, a disadvantage of certain herbicides is that it is necessary to make use of and maintain special handling methods due to their toxic nature. A further wish is such that the herbicide is safe to handle.

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Det er derfor opfindelsens formai at angive en gruppe af herbicide forbindelser, der eliminerer de ovenfor angivne ulemper, der knytter sig til kendt teknik og tilvejebrin-ger et stort antal fordele i forbindelse med en enkelt 5 gruppe af herbicider, at tilvejebringe herbicider, der selektivt kontrollerer og/eller undertrykker vanskeligt udryddelige, flerârige og etârige ukrudt, sàsom de ovenfor angivne, mens de opretholder afgrodesikkerhed i et storre antal afgroder, herunder majs, sojabonner og andre 10 inklusive bomuld, jordnodder, raps og krybbonner, hvede og/eller sorghum, at tilvejebringe herbicid effektivitet i jorden i tidsrum, der strækker sig op til 12 uger, at tilvejebringe herbicider, der modstâr udludning og for-tynding pâ grund af hoje fugtigheder, f.eks. i form af 15 kraftige regnskyl, at tilvejebringe herbicider, der er effektive i forbindelse med mange forskellige typer af jord, f.eks. strækkende sig fra lette til middel.tunge organiske jorder til tungt 1er og dyregodning, at angive herbicider, der udviser fleksibilitet hvad angâr pâfo-20 ringsmetoden, nemlig ved overfladepâforing for spiring og ved inkorporering i jorden, og at angive herbicider, der er sikre, og som ikke kræver nogen specielle hândte-ringsmetoder.It is therefore the object of the invention to provide a group of herbicidal compounds which eliminate the above-mentioned drawbacks associated with the prior art and provide a large number of advantages associated with a single group of herbicides to provide herbicides which selectively controls and / or suppresses difficult to eradicate, perennial and annual weeds, such as those listed above, while maintaining crop security in a greater number of crops, including maize, soybeans and other 10 including cotton, peanuts, rapeseed and creep beans, wheat and / or sorghum; to provide herbicide efficacy in the soil for periods of up to 12 weeks, to provide herbicides that resist leaching and thinning due to high humidity, e.g. in the form of 15 heavy rains, to provide herbicides that are effective in many different types of soil, e.g. ranging from light to medium heavy organic soils to heavy and animal manure, to indicate herbicides which exhibit flexibility in the method of application, namely, surface application for germination and soil incorporation, and to indicate safe herbicides, and which do not require any special handling methods.

Det vil fremgâ af det folgende, at de herbicide forbin-25 delser ifolge opfindelsen, der er af den i indledningen til krav 1 angivne art, og som er ejendommelige ved det i den~ kendetegnende del af krav 1 angivne, opfylder det angivne formâl.It will be apparent from the following that the herbicidal compounds of the invention which are of the kind set forth in the preamble of claim 1 and which are peculiar to the characterizing part of claim 1 fulfill the stated purpose.

Opfindelsen angâr herbicidt aktive forbindelser og herbi-30 eide midler indeholdende disse forbindelser som aktive bestanddele.The invention relates to herbicidally active compounds and herbicides containing these compounds as active ingredients.

Det har nu vist sig, at en selektiv gruppe af 2-halogen-acetanilider, der er karakteristiske ved specifikke kom- 7It has now been found that a selective group of 2-halo-acetanilides, which is characterized by specific com

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binationer af specifikke alkyloxymethyl- eller alkoxyal-kyloxymethyl- eller alkenyloxymethyl- eller alkynyloxy-methylradikaler pâ anilidnitrogenatomet, et trifluorme-thyl (-CF^) radikal i en ortostilling og et methyl-5 eller ethylradikal eller hydrogenatom pâ den anden ortostilling, uventet udviser overlegne og fremragende herbicide egenskaber i sammenligning med kendte herbicider, herunder homologe forbindelser udvalgt blandt de med op-findelsen mest beslægtede, kendte forbindelser.combinations of specific alkyloxymethyl or alkoxyalkyloxymethyl or alkenyloxymethyl or alkynyloxy methyl radicals on the anilide nitrogen atom, a trifluoromethyl (-CF 2) radical in an ortho position and a methyl or ethyl radical or hydrogen atom in the other ortho position, and excellent herbicidal properties in comparison with known herbicides, including homologous compounds selected from among the most well-known known compounds of the invention.

10 Et primært træk ved de herbicide midler eller herbicid- blandingerne ifolge opfindelsen er deres evne til at kon-trollere et bredt spektrum af ukrudt, der kan kontrolle-res af for tiden foreliggende herbicider, og yderligere et stort antal ukrudt, der - individuelt og/eller kollek-15 tivt - hidtil ikke har kunnet kontrolleres ved hjælp af en enkelt klasse af kendte herbicider, mens man bibeholdt sikkerheden af afgroden i forbindelse med en eller flere af et storre antal afgrodeplanter, herunder især soja-bonner og majs, men ogsâ andre, sâsom bomuld, jordnodder, 20 raps, sorghum, hvede og brydbonner. Mens kendte herbicider er anvendelige til at kontrollere mange forskellige ukrudt, herunder lejlighedsvis visse resistente ukrudt, har det vist sig, at de enestâende herbicider ifolge opfindelsen er i stand til at kontrollere eller i hoj grad 25 at undertrykke et stort antal resistente flerârige og et-ârige ukrudtsarter, sâsom det flerârige kvikgræs, gui og purpur "nutsedge", etârige, btedbladede planter, sâsom tornet sida, hamp sesbania, vandpeber, hvidmelet gâsefod, kvinoa og etârige græsser, sâsom durra-kimplanter, "shat-30 tercane", alexandergraes, Texas panicum, vild prosohirse, rod ris, klogræs og andre skadelige ukrudtsarter, sâsom eftèrârspanicum, rævehaler, hanespore, fingeraks, ovs. Reduktion af ukrudtsvækster er ogsâ opnâet ved resistente ukrudtsarter, sâsom engbrandbæger, flojlsblad, ipomoea, 35 brodfro, portulak osv.A primary feature of the herbicides or herbicide compositions of the invention is their ability to control a broad spectrum of weeds that can be controlled by currently available herbicides, and a further large number of weeds that - individually and / or collectively - so far it has not been possible to control by a single class of known herbicides while maintaining the safety of the crop in connection with one or more of a large number of crop plants, including especially soybeans and maize, but also others, such as cotton, peanuts, 20 rapeseed, sorghum, wheat and groundnuts. While known herbicides are useful for controlling many different weeds, including occasionally certain resistant weeds, it has been found that the unique herbicides of the invention are able to control or to a great extent suppress a large number of resistant perennials and annual weeds, such as the perennial mercury, gui and purple "nutsedge", annual, leafy plants, such as thorny side, hemp sesbania, pepper, white flour goose foot, quinoa and annual grasses, such as durra seedlings, "shat-30 tercane" , Texas panicum, wild prose millet, root rice, clover grass, and other harmful weed species, such as eftèráspanicum, fox tails, male grouse, finger axis, ovs. Reducing weed growth has also been achieved by resistant weed species, such as meadow firebrand, phyllo leaf, ipomoea, 35 hedgehogs, porcelain, etc.

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Foretrukne forbindelser ifolge opfindelsen er sâdanne, hvori i den i krav 1 angivne formel er methyl eller ethyl, og hvor R er et C^^-alkylradikal. Individuelle, foretrukne forbindelser ifolge opfindelsen er folgende: 5 N-(ethoxymethyl)-2 *-trifluormethyl-6'-ethyl-2-chloracet-anilid.Preferred compounds of the invention are those in which the formula of claim 1 is methyl or ethyl and wherein R is a C 1-4 alkyl radical. Individual preferred compounds of the invention are as follows: 5 N- (ethoxymethyl) -2 * -trifluoromethyl-6'-ethyl-2-chloroacet anilide.

N-(n-propoxymethyl)-21-trifluormethyl-6 *-methyl-2-chlor-acetanilid.N- (n-propoxymethyl) -21-trifluoromethyl-6 * -methyl-2-chloro-acetanilide.

N-(isopropoxymethyl)-2'-trifluormethyl-6'-methyl-2-chlor-10 acetanilid.N- (isopropoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloro-acetanilide.

N-(ethoxymethyl)-2 *-trifluormethyl-61-ethyl-2-chloracet-anilid.N- (ethoxymethyl) -2 * -trifluoromethyl-61-ethyl-2-chloroacet anilide.

N-(n-propoxymethyl)-2'-trifluormethyl-6'-ethyl-2-chlor-acetanilid.N- (n-propoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide.

15 N-(isopropoxymethyl)-21-trifluormethyl-6'-ethyl-2-chlor- . acetanilid.N- (isopropoxymethyl) -21-trifluoromethyl-6'-ethyl-2-chloro-. acetanilide.

André udforelsesformer for opfindelsen vil blivë beskre-vet i det folgende.Other embodiments of the invention will be described hereinafter.

Anveridëïigheden af forbindelserne ifol’ge opfindelsen som 20 den aktive bestanddel i herbicide blandinger, der er formuler et dermed, og fremgangsmâden til anvendelse deraf vil blive beskrevet i det falgende.The utility of the compounds of the invention as the active ingredient in herbicidal mixtures formulated therewith, and the process for its use will be described below.

Forbindelserne ifolge opfindelsen kan fremstilles ved N-alkylering af anionen af det passende sekundære 2-halogen-25 acetanilid med et alkyleringsmiddel under passende basi- ske betingelser, som eksemplificeret i eksempel 1. Modi- fïkation af den angivne N-alkyleringsproces involvererThe compounds of the invention may be prepared by N-alkylation of the anion of the appropriate secondary 2-halo-acetanilide with an alkylating agent under appropriate basic conditions as exemplified in Example 1. Modification of the N-alkylation process disclosed involves

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9 in situ fremstillingen af halogenmethylalkylethere anvendt som udgangsmaterialer i N-alkyleringsprocessen og er be-skrevet i eksempel 2 med henblik pâ fremstilling af en anden forbindelse ifolge opfindelsen.9 shows the in situ preparation of halo methyl alkyl ethers used as starting materials in the N-alkylation process and is described in Example 2 for the preparation of another compound according to the invention.

5 EKSEMPEL 1EXAMPLE 1

Dette eksempel beskriver fremstillingen af N-(ethoxyme-thyl)-2'-trifluormethyl-6'-methyl-2-chloracetanilid.This example describes the preparation of N- (ethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide.

4,02 g (0,015 mol) 2’-trifluormethyl-6,-methyl-2-chlor-acetanilid, 3,02 g (0,032 mol) chlormethylethylether og 10 2,0 g benzyltriethylammoniumbromid, (faseoverforingska- talysator) blev blandet i 75 ml methylenchlorid i en 500 ml rundbundet beholder forsynet med mekanisk omrorer og termometer. Natriumhydroxid (50%), 15 ml, blev tilsat i en portion under kraftig omrcring, hvilket giver anled-15 ning til fremkomsten af en exoterm til 26 °C Efter ca.4.02 g (0.015 mole) of 2'-trifluoromethyl-6, methyl-2-chloro-acetanilide, 3.02 g (0.032 mole) of chloromethylethyl ether and 2.0 g of benzyl triethylammonium bromide (phase transfer catalyst) were mixed in 75 ml of methylene chloride in a 500 ml round bottom vessel equipped with mechanical stirrer and thermometer. Sodium hydroxide (50%), 15 ml, was added in one portion under vigorous stirring, giving rise to an exotherm to 26 ° C.

5 minutters forlob viste det sig ved gaschromatografi, at reaktionen var færdig. Efter 15 minutter tilsættes is og vand, lagene blev separeret, og det organiske lag blev vasket med 2,5% natriumchlorid, torret, filtreret og de-20 stilleret. Den morktfarvede remanens blev destilleret pâAfter 5 minutes, gas chromatography showed that the reaction was complete. After 15 minutes, ice and water are added, the layers are separated and the organic layer is washed with 2.5% sodium chloride, dried, filtered and distilled. The dark colored residue was distilled on

Kugelrohr, og man opsamlede 3,4 g af en gui oliefraktion, der kogte ved 110 - 115 °C ved 0,01 mm Hg. Denne fraktion blev optaget i cyclohexan og renset ved hjaelp af HPLC med 20% ethylacetat i cyclohexan. Ved yderligere destination af 25 topfraktionen med Kugelrohr fremkom der 3,2 g (65% ud- bytte) farvelos olie med kp. 100 - 110 °C ved 0,1 mm Hg; ved henstand udkrystalliserede et hvidt, fast stof med smp. 41 - 43 °C.Kugelrohr and 3.4 g of a gui oil fraction boiling at 110 - 115 ° C were collected at 0.01 mm Hg. This fraction was taken up in cyclohexane and purified by HPLC with 20% ethyl acetate in cyclohexane. At a further destination of the top 25 fraction with Kugelrohr, 3.2 g (65% yield) of colorless oil with bp were obtained. 100 - 110 ° C at 0.1 mm Hg; upon standing, a white solid crystallized with m.p. 41 - 43 ° C.

Analyse for C^3H15C1F3N02(%) Grundstof Teori Fundet 30 C 50,41 50,02 H 4,88 4,81 N 4,52 4,38 10Analysis for C 13 H 15 ClF 3 NO 2 (%) Element Theory Found 30 C 50.41 50.02 H 4.88 4.81 N 4.52 4.38

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EKSEMPEL 2EXAMPLE 2

Dette eksempel illustrerer anvendelsen af en forbedret alternativ procès, ved hvis hjælp forbindelserne ifolge opfindelsen kan fremstilles. Et træk ved fremgangsmâden 5 i henhold til dette eksempel er in situ dannelsen af al-kyleringsmidlet, hvorved der fremkoinmer en mere effektiv okonomisk og simpel operation.This example illustrates the use of an improved alternative process by which the compounds of the invention can be prepared. A feature of the method 5 of this example is the in situ formation of the alkylating agent, thereby providing a more efficient economical and simple operation.

7,3 g (0,096 mol) af en opslæmning af ethylenglycolmono-metbylether og 1,44 g (0,048 mol) paraformaldehyd i 100 10 ml methylenchlorid-oplosningsmiddel blev afkolet i et is-vandbad og 5,9 g (0,048 mol) acetylbromid blev tilsat.7.3 g (0.096 mole) of a slurry of ethylene glycol monomethyl ether and 1.44 g (0.048 mole) of paraformaldehyde in 100 ml of methylene chloride solvent were cooled in an ice-water bath and 5.9 g (0.048 mole) of acetyl bromide were added. added.

Efter omrering i ca. 45 minutter tilsattes 4,03 g (0,015 mol) 2,-trifluormethyl-6,-methyl-2-chloracetanilid og 2,0 g benzyltriethylammoniumchlorid. 50 ml 50% NaOH blev 15 tilsat i én portion. Gaschromatografi viste fuldstændig reaktion efter ca. 5 minutter. Der tilsattes isvand til blandingen til frembringelse af faseseparation, og den organiske fase blev separeret, torret, filtreret og de-stilleret. Remanensen blev vacuumdestilleret i et kort-20 banet destillationsapparat til dannels af 4,2 g (77% udbytte) af klar, farvelos olie, kp. 150 - 160 °C ved 0,05 mm Hg.After stirring for approx. For 45 minutes, 4.03 g (0.015 mol) of 2, -trifluoromethyl-6, -methyl-2-chloroacetanilide and 2.0 g of benzyltriethylammonium chloride were added. 50 ml of 50% NaOH was added in one portion. Gas chromatography showed complete reaction after approx. 5 minutes. Ice water was added to the mixture to produce phase separation and the organic phase was separated, dried, filtered and distilled. The residue was vacuum distilled in a short-pane distillation apparatus to give 4.2 g (77% yield) of clear, colorless oil, b.p. 150 - 160 ° C at 0.05 mm Hg.

Abalyse for C-^H^ClF^NO^ ( % ) Grundstof Teori Fundet C 49,49 49,33 25 H 5,04 5,04 N 4,12 4,08Analysis for C- CH HClF ^NO ^ (%) Element Theory Found C 49.49 49.33 H H 5.04 5.04 N 4.12 4.08

Produktet blev identificeret soin N-( 2-methoxyethoxyme-thyl)-21-trifluormethy1-61-methyl-2-chloracetanilid.The product was identified as N - (2-methoxyethoxymethyl) -21-trifluoromethyl-61-methyl-2-chloroacetanilide.

Hvis man lader N-alkyleringsprocessen udvikle for hoje 30 eller for lave temperaturer, kan der dannes forskellige urenheder, f.eks. sek.-anilid, tilsvarende imidat, a-alk- 11If the N-alkylation process is allowed to develop too high or too low, various impurities can be formed, e.g. sec-anilide, corresponding to imidate, α-alk-11

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oxyamid eller diketopiperaziner. Sâdanne urenheder kan fjernes ved at vaske det organiske lag med et fortyndet, organisk sait af en sur oplosning, f.eks. 2-3% NaCl el-1er 5% HCl.oxyamide or diketopiperazines. Such impurities can be removed by washing the organic layer with a dilute, organic solution of an acidic solution, e.g. 2-3% NaCl or 1% 5% HCl.

5 EKSEMPEL 3-13EXAMPLES 3-13

Idet man x det væsentlige gar brug af de samme metoder, mængder af reaktanter og generelle reaktkonsbetingelser, sont beskrevet i eksempel 1 eller 2, men idet man ger brug af passende, som udgangsmaterialer tjenende, sek.-anilid 10 og alkyleringsmiddel til opnâelse af slutproduktet, frem- stilles andre forbindelser ifalge den ovenfor angivne formel; disse forbindelser er identificeret i tabel I.By substantially using the same methods, amounts of reactants and general reaction conditions, as described in Examples 1 or 2, but using appropriate starting materials, sec-anilide 10 and alkylating agent to obtain the final product. , other compounds are prepared according to the above formula; these compounds are identified in Table I.

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De som udgangsmaterialer tjenende sekundære anilider, der anvendes i de for angivne eksempler til fremstilling af forbindelser ifelge opfindelsen, fremstilles passende ved konventionel chloracetylering af den passende primære amin, 5 som eksemplificeret i det f0lgende eksempel.The secondary anilides used as starting materials used in the examples given for the preparation of compounds of the invention are suitably prepared by conventional chloroacetylation of the appropriate primary amine, as exemplified in the following example.

EKSEMPEL PA FREMSTILLING AF UDGANGSM&TERIALEEXAMPLE OF PREPARATION OF OUTPUT & TERIAL

Dette eksempel illustrerer fremstillingen af det som ud-gangsmateriale tjenende sekundære anilid, der anvendes til fremstilling af dette eksempels udforelsesform for forbin-10 delsen, dvs. forbindelsen fra eksempel 13.This example illustrates the preparation of the secondary anilide serving as a starting material used in the preparation of this example embodiment of the compound, i.e. the compound of Example 13.

6,0 g (0,031174 mol 2-trifluormethyl-6-ethylanilin blev oplost i 75 ml toluen, og 3,77 g (0,033 mol) chloracetyl-chlorid blev forsigtigt tilsat. Temperaturen af den resul-terende opslæmning blev hævet til tilbagesvaling og holdt der i 4 timer. Derpâ blev blandingen fortyndet med et lige 15 sâ stort volumen hexan, og man lod blandingen henstâ. Pro-duktet krystalliserede og det resulterende faste stof blev filtreret og lufttorret til dannelse af 5,8 g (69% udbytte); filtratet blev destilleret til dannelse af andre 2,7 g hvidt fast stof, smp. 121 - 124° C.6.0 g (0.031174 mol of 2-trifluoromethyl-6-ethylaniline) was dissolved in 75 ml of toluene and 3.77 g (0.033 mol) of chloroacetyl chloride was gently added. The temperature of the resulting slurry was raised to reflux. The mixture was diluted with an equal volume of hexane and the mixture was left to stand. The product crystallized and the resulting solid was filtered and air dried to give 5.8 g (69% yield) ), the filtrate was distilled to give another 2.7 g of white solid, mp 121 - 124 ° C.

20 (forseglet ror).20 (sealed rudder).

Analyse for C^H-^C1F^N0 (%) Grundstof Teori fundet C 49,73 49,36 H 4,17 4,07 N 5,-27 5,33Analysis for C ^H- ^C1F ^NO (%) Element Theory Found C 49.73 49.36 H 4.17 4.07 N 5, -27 5.33

Produktet blev identificeret som 2’-trifluormethyl-6'-ethyl-2-chloracetanilid.The product was identified as 2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide.

Primære aminer af den type, der anvendes til fremstilling af sekundære anilider ved halogenacetylering, som f0r be-25 skrevet, er kendt i litteraturen, jvf. f.eks. det fer angivne US patentskrift nr.' 3. 9.66 811' og GB patentansogning tPrimary amines of the type used for the preparation of secondary anilides by haloacetylation previously described are known in the literature, cf. U.S. Pat. 3. 9.66 811 'and GB patent application t

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15 nr. 2 013 188.15 No. 2,013,188.

Soin anfort i det foregâende har det vist sig, at forbin-delserne ifolge opfindelsen er effektive som herbicider, især som herbicider for spiringen, skont aktivitet efter 5 spiring ogsâ er blevet pâvist. De forsog, der blev udfort for spiringen, og hvortil der her er henvist, omfatter bâde drivhus- og markprover. Ved drivhusproverne pâfores herbicidet enten ved overfladeapplikation efter sâning af froene eller plantning af de végétative formeringsor-10 ganer eller ved inkorporering i en mængde af jord, der skal pâfores som et dæklag over forsogsfroene i forud til-sàede forsogsbeholdere. Ved markproverne kan herbicidet pâfores ved inkorporering for sâningen ("P.P.I.") i jor-den, dvs. herbicidet pâfores pà overfladen af jorden, og 15 det bliver derpâ inkorporeret deri ved hjælp af blande- organer, efterfulgt af sâning af afgrodefroene, eller herbicidet kan pâfores pâ overfladen ("S.A.", overfladeapplikation) efter at afgrodefroene er sâet.In the foregoing, it has been found that the compounds of the invention are effective as herbicides, especially as herbicides for germination, spawning activity after germination has also been demonstrated. The experiments that were performed for the germination, and to which reference is made here, include both greenhouse and field samples. In the greenhouse samples, the herbicide is applied either by surface application after sowing the seeds or planting the vegetative propagating organs or by incorporating into an amount of soil to be applied as a cover layer over the test seeds in pre-sown test containers. In the field tests, the herbicide can be applied by incorporation for sowing ("P.P.I.") into the soil, ie. the herbicide is applied to the surface of the soil and it is then incorporated therein by means of mixing means, followed by seeding the crop seed, or the herbicide can be applied to the surface ("S.A.", surface application) after the seed seed is sown.

Forsogsmetoden i forbindelse med overfladepâforingen ("S.The test method for the surface application ("S.

20 A.") anvendt i drivhus gennemfores pâ folgende mâde: Be- holdere, f.eks. aluminiumskâle, der typisk har dimensio-nerne 24,13 cm x 13,34 cm x 6,99 cm, eller formstofpotter med dimensionerne 9,53 cmx 9,53 cmx 7,62 cm, hvori der er drænhuller i bunden, fyldtes til niveau med lerdynd af 25 Ray-typen og komprimeres derpâ til et niveau af 1,27 cm fra toppen af potterne. Potterne bliver derpâ tilsâet med fro af plantearter, der skal undersoges, og de bliver dækket med et 1,27 cm tykt lag af den jord, der skal undersoges. Herbicidet bliver derpâ pâfort pâ overfladen 30 af jorden, f.eks. med et bæltesprojteorgan, med 1,87 1/ha og 2,11 kg/cm . Hver potte optager 0,64 cm som ovenfra kommende kunstig vanding, og potterne bliver derpâ anord-net pâ drivhusbænke med henblik pâ nedefra kommende, kunstig vanding efter behov. Som en alternativ metode kan20 A. ") used in greenhouses shall be carried out as follows: Containers, for example, aluminum bowls, typically having dimensions of 24.13 cm x 13.34 cm x 6.99 cm, or plastic pots having dimensions 9, 53 cmx 9.53 cmx 7.62 cm, in which there are drainage holes in the bottom, were filled to level with 25 Ray type clay pads and then compressed to a level of 1.27 cm from the top of the pots. of the plant species to be examined and covered with a 1.27 cm thick layer of soil to be examined The herbicide is then applied to the surface 30 of the soil, for example with a belt sprayer, with 1.87 l / ha and 2.11 kg / cm.Each pot occupies 0.64 cm as above artificial irrigation from above, and the pots are arranged on greenhouse benches for downward artificial irrigation as needed.

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16 den kunstige vanding ovenfra undgâs. Observationer af herbicide virkninger gores ca. tre uger efter behandling.16 the artificial irrigation from above was avoided. Observations of herbicidal effects are made approx. three weeks after treatment.

Den herbicide behandling ved inkorporering i jord ("S.I.") anvendt i drivhusforosg er som folger: 5 En god kvalitet af overfladejord indfores i aluminiumskâ-le og komprimeres til en dybde af 0,95 cm til 1,27 cm fra toppen af skâlen. Pâ toppen af jorden indfares der et antal fro eller végétative formeringsorganer af forskel-lige plantearter. Den jord, der kræves til at fylde skâ-10 lene til niveau efter sâning eller tilforing af végétative formeringsorganer, indvejes i en skâl. Jorden og en kendt mængde af den aktive bestanddel, der pâfores i et oplcsningsmiddel eller som en suspension af et befugte-ligt pulver, blandes grundigt og anvendes til at dække 15 de behandlede skâle. Efter behandling udsætter man skâ-lene for en initial, kunstig, ovenfra kommende vanding, der er ækvivalent med 0,64 cm regnfald, og derpâ vandes der kunstigt med nedefra kommende vand efter behov til frembringelse af passende fugtighed til spiring og vækst.The herbicidal treatment by incorporation into soil ("S.I.") used in greenhouse forests is as follows: 5 A good quality of surface soil is introduced into aluminum casing and compacted to a depth of 0.95 cm to 1.27 cm from the top of the shell. At the top of the soil, a number of seed or vegetative propagating organs of different plant species are entered. The soil required to fill the bowls to level after sowing or feeding vegetative propagating organs is weighed into a bowl. The soil and a known amount of the active ingredient applied in a solvent or as a suspension of a wettable powder are thoroughly mixed and used to cover the treated bowls. After treatment, the bowls are subjected to an initial, artificial, top-down irrigation equivalent to 0.64 cm of rainfall, and then artificially irrigated with bottom-up water as needed to produce appropriate moisture for germination and growth.

20 Som alternativ metode kan man undgâ den kunstige vanding ovenfra. Man foretager sine iagttagelser ca. 2-3 uger efter sâning og behandling.20 As an alternative method, artificial irrigation can be avoided from above. You make your observations approx. 2-3 weeks after sowing and treatment.

Tabel II og III sammenstiller resultaterne af forsog, der er gennemfort for at bestemme den herbicide aktivitet for 25 spiring af forbindelserne ifolge opfindelsen? ved disse forsog pâfores herbiciderne ved inkorporering i jorden og udelukkende ved kuns-tig- vanding nedefra. Den herbicide karakter fremkom ved hjælp af en fikseret skala pâ basis af den procentiske beskadigelse af hver planteart. Karak-30 tererne er defineret pâ folgende mâde:Tables II and III summarize the results of experiments conducted to determine the herbicidal activity for germination of the compounds of the invention? In these experiments, the herbicides are applied by incorporation into the soil and exclusively by artificial irrigation from below. The herbicidal nature was obtained using a fixed scale based on the percentage damage to each plant species. The characters are defined as follows:

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17 % Kontrol Karaktergivninq 0 - 24 0 25 - 49 1 50-74 2 75 - 100 3 ubestemt 517% Control Grading 0 - 24 0 25 - 49 1 50-74 2 75 - 100 3 indefinite 5

De plantearter, der an.vendes i et sæt af pr0ver, hvis data er vist i tabel II, er identificeret ved et bogstav i henhold til felgende oversigt: A Agertidsel E Hvidmelet gâsefod I Durra græs B Brodfro F Vandpeber J Taghejre C Flojlsblad G Gui "nutsedge" K Hanespore D Ipomoea H KvikgræsThe plant species used in a set of specimens, the data of which are shown in Table II, are identified by a letter according to the following summary: A Agder thistle E White flour goose foot I Durra grass B Brodfro F Water pepper J Rooster C Flojlsblad G Gui "nutsedge" K Hanespore D Ipomoea H Mercury

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1818

TABEL IITABLE II

Forbindelse fraConnection from

eksempel nr. -kg/h A B C Q E F 0 H I_J—KExample No. -kg / h A B C Q E F 0 H I_J — K

1 11.2 5 3^ 3 3 3 3 3 3 3 3 5.6 5 2 2 1 3. 3 .1 3 3 3 3 2 11.2 9 1 1 3 2 2 3 3 3 3 3 .1 11.2 5 3 ^ 3 3 3 3 3 3 3 3 5.6 5 2 2 1 3. 3 .1 3 3 3 3 2 11.2 9 1 1 3 2 2 3 3 3 3 3.

5.6 3 2 1 3 2 3 0 2 2 3 3 3 1 1,2 3 1 2 3 3 3 3 1 2 .3 3 5.6 2 0 3 3 3 2 3 3 1 3 3 4 11,2 5 3 2 3 3 3 3 3 3 ?, 3 5.6 5 2 1 2 3 3 3 3 3 3 3 5 11,2 5 3 2 3 3 3 3 3 .3 3 3 5.5 5 0 0 3 3 3 3 3 ! 3 3 6 11,2 5 2 1 3 3 3 3 3 3 3 3 5.5 5 2 0 1 3 3 3 3 3 3 3 7 11,2 312 2 30 2 31 3 3 5.6 10 113 0 13 13 3 H 11,2 3 2 0 2 .3 3 3 3 3 3 3 5.5 3 1 0 2 3 3 3 3 2 3 3 9 11,2 7 2 2 1 3 3 3 3 3 3 3 5.6 3 2 1 2 2 3 3 3 1 2 3 10 11,2 3 2 1 3 3 3 -ï 3 3 3 3 5.6 3 1 1 2 3 3 3 3 0 3 3 11 11,2 3 1 1 3 3 3 3 3 0 3 3 5.6 3 1 1 2 3 3 1 3 1 3 3 12 il ? 3 2 0 2 3 3 3 3 0 3 3 5.6 3 1 0 2 1 2 3 3 3 3 3 1 11,2 3 2 233 33 3 33 3 5.6 3 2 2 3 3 3 3 3 2 3 3 195.6 3 2 1 3 2 3 0 2 2 3 3 1 1 1.2 3 1 2 3 3 3 1 2 .3 3 5.6 2 0 3 3 3 2 3 3 1 3 3 4 11.2 5 3 2 3 3 3 3 3 3?, 3 5.6 5 2 1 2 3 3 3 3 3 3 3 5 11.2 5 3 2 3 3 3 3 .3 3 3 5.5 5 0 0 3 3 3 3 3! 3 3 6 11.2 5 2 1 3 3 3 3 3 3 3 3 5.5 5 2 0 1 3 3 3 3 3 3 3 7 11.2 312 2 30 2 31 3 3 5.6 10 113 0 13 13 3 H 11, 2 3 2 0 2 .3 3 3 3 3 3 3 5.5 3 1 0 2 3 3 3 2 3 3 9 11.2 7 2 2 1 3 3 3 3 3 3 5.6 3 2 1 2 2 3 3 3 1 2 3 10 11.2 3 2 1 3 3 3 -ï 3 3 3 3 5.6 3 1 1 2 3 3 3 3 0 3 3 11 11.2 3 1 1 3 3 3 3 3 0 3 3 5.6 3 1 1 2 3 3 1 3 1 3 3 12 il? 3 2 0 2 3 3 3 3 0 3 3 5.6 3 1 0 2 1 2 3 3 3 3 3 1 11.2 3 2 233 33 3 33 3 5.6 3 2 2 3 3 3 3 2 3 3 19

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L Sojab0nne R Hamp Sesbania M Sukkerroe E Hvidmelet gâsefod N Hvede F Vandpeber 0 Ris C Fl0jlsblad P Sorghum J Taghejre B Brodfr0 S Panicum spp, Q Vild boghvede ' K Hanespore D Ipomoea T FingeraksL Soybean R Hemp Sesbania M Beetroot E White flour goose foot N Wheat F Water pepper 0 Rice C Leaf leaf P Sorghum J Rare B Brodfr0 S Panicum spp, Q Wild buckwheat 'K Male track D Ipomoea T Fingeraks

Resultaterne er sammenstillet i tabel III.The results are summarized in Table III.

TABEL III (f0r spiring)TABLE III (before germination)

Forbindelse Ira eksempel nr_ kq/h L Μ M 0 P B _Q p R Ξ F_ç. -7 <__£ 1 5,6 1233303333323333 1.12 0112301223203333 0,23 0102101033302333 0 T 053 ÛOOOOOOC11 1 00223 0,0112 0000000001100122 2 5,6 1323312333303335 1.12 0323201312203335 0,23 0201100111003335 0,055 ClOOOOCOOO 001135 0,0112 0000000000000015 3 5,5 0333313333313333 1.12 0113310313003333 0,28 00022 n 00 03001333 0,055 0 0 0 1 0 0 0 9 0 2 3 0 C 3 3 3 0,0112000000 0001 000333 0,0955 00000000 030001 01 4 5,5 2333323333313333 1.12 122331.3233313333 0,23 0122101013302333 0,055 0111221021100223 0,0112 0190000001000333 5 5 5 1 2 3 3 3 1 3 3 3 3 3 1 3 3 3 3 1.12 0223302023303333 0,28 0213322323303333 0,0 5·5 0 1 0 1 2 1 2 0 1 3 1 0 2 3 3 3 0,0112 0 1 0 0 9 1 1 0 0 3 1 C 1 2 3 3 20Compound Ira Example nr_kq / h L Μ M 0 P B _Q p R Ξ F_ç. -7 <__ £ 1 5.6 1233303333323333 1.12 0112301223203333 0.23 0102101033302333 0 T 053 ÛOOOOOOC11 1 00223 0.0112 0000000001100122 2 5.6 1323312333303335 1.12 0323201312203335 0.23 0201100111003335 0.055 Clone 0113310313003333 0.28 00022 n 00 03001333 0.055 0 0 0 1 0 0 0 9 0 2 3 0 C 3 3 3 0.0112000000 0001 000333 0.0955 00000000 030001 01 4 5.5 2333323333313333 1.12 122331.3233313333 0.23 0122101013302333 0.055 011122102 , 0112 0190000001000333 5 5 5 1 2 3 3 3 1 3 3 3 3 1 3 3 3 3 1.12 0223302023303333 0.28 0213322323303333 0.0 5 · 5 0 1 0 1 2 1 2 0 1 3 1 0 2 3 3 3 0.0112 0 1 0 0 9 1 1 0 0 3 1 C 1 2 3 3 20

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TABEL III (fortsat)TABLE III (continued)

Forbindelse fra (f0r spiring)Connection from (before germination)

eksenrpel nr. kg/h lmnopbqdrsf^JSaTExample No. kg / h lmnopbqdrsf ^ JSaT

6 5,5 13333.2 3333313333 1.12 0103313313303333 0,23 0202222133303333 0,055 0201212223102333 0. 0112 0201022223101133 7 5,5 032230222 3 003333 1, 12 010010 -1 002000233 0,23 0000001200000223 0,055 0101000003200023 8 5,5 23 3 33233333133 3 3 1.12 1233302013303333 0,23 0121202021102333 0,055 0011100001101333 0,0112 1000010010001023 9 5,5 2233323332313333 1.12 1233-113122203333 0,23 12232011211 0 3-3 33 0,055 0 0 0 0 C 0 0 0 0 2 1.0 2 3 3 3 0,01120000000000000033 10 5,5 3333323333303333 1.12 1233303322303333 C, 23 02222 0 1023203333 0 055 0101000010000333 0,0112 0000000000000123 11 5,5 0 3 3 3 3 1 3 3 3 3 3 1 3 3 3 -ΞΙ, 12 0 313111212203335 0,28 02 121000 11103335 0,056 01000000500 01235 0,011201000000 00 C001 35 12 5,5 1223 3'12' 2021 0 3 3 3 3 1.12 1212302212203333 0.28 0 101001001 C 01232 0,05-5 050000500 0 000020 1 5,5 2333323333323333 1.12 1233302232303333 0,23 2233101031302333 0,05' 0111001000002333 O,0112 000000 00155000226 5.5 13333.2 3333313333 1.12 0103313313303333 0.23 0202222133303333 0.055 0201212223102333 0. 0112 0201022223101133 7 5.5 032230222 3 003333 1, 12 010010 -1 002000233 0.23 0000001200000223 0.055 010100000223 0.055 010100000223 0.055 01010033 , 23 0121202021102333 0.055 0011100001101333 0.0112 1000010010001023 9 5.5 2233323332313333 1.12 1233-113122203333 0.23 12232011211 0 3-3 33 0.055 0 0 0 0 C 0 0 0 0 2 1.0 2 3 3 3 0.01120000000000000033 10 5.5 3333323333303333 1.12 1233303322303333 C, 23 02222 0 1023203333 0 055 0101000010000333 0.0112 0000000000000123 11 5.5 0 3 3 3 3 1 3 3 3 3 3 1 3 3 3 -ΞΙ, 12 0 313111212203335 0.28 02 121000 11103335 0.056 01000000500 01235 0.011201000000 00 C001 35 12 5.5 1223 3'12 '2021 0 3 3 3 3 1.12 1212302212203333 0.28 0 101001001 C 01232 0.05-5 050000500 0 000020 1 5.5 2333323333323333 1.12 1233302232303333 0.23 2233101031302333 0.05 '0111001000002333 O, 0112 000000 0015500022

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2121

Herbiciderne ifolge opfindelsen har vist sIg at være i besiddelse af uventet overraskende egenskaber som selek-tive herbicider f0r spiringen, især den selektive kontrol af de vanskeligt udryddelige, flerârige og etârige ukrudt, 5 herunder sâdanne flerârige planter som kvikgræs, gui og pur-pur "nutsedge", etârige bredbladede ukrudt, sâsom tornet sida, hamp Sesbania, vandpeber, hvidmelet gâsefod, kvinoa og etârige græsser, sâsom HshattercaneS!, alexandergræs, durra, Texas panicum, vild proso-hirse, rod ris, klogræs, 10 Raoulgræs; Rottboellia exaltata, rævehale (f. eks. gron og gui rævehale og kæmperævehale), hanespore og stort finger-aks. Reduktion af ukrudtsbestanden er ogsâ blevet opnâet i forbindelse med andre resistente arter, sâsom engbrand-bæger, flojlsblad, ipomoea, brodfr0, portulak, osv.The herbicides of the invention have been shown to possess unexpectedly surprising properties such as selective herbicides prior to germination, in particular the selective control of the difficult extinct, perennial and annual weeds, including such perennial plants as mercury, gui and pure ". nutsedge ", annual broadleaf weeds, such as thorny side, hemp Sesbania, pepper, white flour goose foot, quinoa and annual grasses, such as HshattercaneS !, alexander grass, sorghum, Texas panicum, wild prose millet, root rice, clover grass, 10 Raoul grass; Rottboellia exaltata, fox tail (eg throat and gui fox tail and giant fox tail), male groove and large finger axis. Reduction of the weed population has also been achieved in connection with other resistant species, such as meadow-goblet, phyllo leaf, ipomoea, brodfr0, portulak, etc.

15 Man har konstateret selektiv kontrol og foroget undertryk-kelse af de ovenfor angivne ukrudtsarter med herbiciderne ifolge opfindelsen i mange forskellige afgr0der, herunder især majs, sojabonner, men ogsâ andre, sâsom bomuld, jord-nodder, raps, brydbonner (krybbonner), hvede og sorghum; 20 de sidste to afgr0der er imidlertid sædvanligvis mindre tolérante overfor herbiciderne if0lge opfindelsen end de andre, angivne afgroder; en sâdan reduceret tolérance kan forbed-res ved anvendelse af sikringsmidler, dvs. herbicide mod-gifte.Selective control and suppression of the herbicides listed above with the herbicides of the invention have been found in many different crops, including in particular corn, soybeans, but also others, such as cotton, groundnuts, rapeseed, groundnuts (creepers), wheat and sorghum; However, the last two crops are usually less tolerant to the herbicides of the invention than the other specified crops; such a reduced tolerance can be improved by the use of safeguards, ie. herbicidal antidotes.

25 Ved den f0lgende diskussion af de nedenfor anforte tabeller og data henvises der til herbicide pâf0ringsintensiteter, der er symboliseret som "GR^ " og "GRg^”; disse pàforings-intensiteter er angivet i kg/ha, der kan konverteres til lbs/A ved at dividere med 1,12. GR-^ definerer den maxi-30 male pâforingsintensitet af herbicid, som kræves til at op-nâ 15% afgr0debeskadigelse eller derunder, og GRg^ definerer den minimale pâforingsintensitet, der kræves til at opnâ 85% inhibering af ukrudtet. GR-^ og GRg^ pâforingsinten-siteterne anvendes som mâl for potentiel kommerciel anvendel-35 se, idet det naturligvis mâ fôrstâs, at passende kommerciel-25 In the following discussion of the tables and data set forth below, reference is made to herbicidal application intensities symbolized as "GR ^" and "GRg ^", these loading intensities are given in kg / ha which can be converted to lbs / A by dividing by 1.12 GR- ^ defines the maximum herbicide application intensity required to reach or below 15% crop damage, and GR GRg defines the minimum application intensity required to achieve 85% inhibition. The GR- and GR₂ levels of the feeding intensities are used as targets for potential commercial use, since it is of course necessary to understand that appropriate commercial

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22 le herbicider kan udvise st0rre eller mindre plantebeska-digelser indenfor rimelige grænser.22 le herbicides may exhibit greater or lesser plant damage within reasonable limits.

En yderligere vejledning til effektiviteten af et kemika-lium som selektivt herbicid er "selektivitetsfaktorenn 5 ("SF") for et herbicid i givne afgroder og ukrudt. Selekti- vitetsfaktoren er et mâl for den relative afgrodesikkerheds-grad og ukrudtsbeskadigelse, og den udtrykkes som forholdet GR^/GRq^, altsâ GR^ pâforingsintensiteten for afgro-den divideret med GRg^ pâforingsintensiteten for ukrudtet, 10 begge pâforingsintensiteter i kg/ha (lbs/Α). Nâr selektivi-tetsfaktorerne i det folgende er anfort i tabelleme, er de vist i parentes efter GRg^ pâforingsintensiteten for hvert ukrudt; symbolet "NS" betÿder "ikke selektiv"; marginal eller ikke bestemt selektivitet angives ved bindestreg (-)' 15 efter ukrudtet «A further guide to the effectiveness of a chemical as a selective herbicide is the "selectivity factor 5 (" SF ") for a herbicide in given crops and weeds. The selectivity factor is a measure of the relative degree of crop security and weed damage, and it is expressed as the ratio GR ^ / GRq ^, i.e. GR ^ application intensity for the crop divided by GRg ^ application intensity for the weeds, 10 both application intensities in kg / ha (lbs / Α) .When the selectivity factors are listed below, they are shown in parentheses according to GRg ^ application intensity for each weed; symbol "NS" means "non-selective"; marginal or undetermined selectivity is indicated by dash (-) '15 after the weed'

Da afgrodetolerance og ukrudtskontrol er indbyrdes afhæn-gige, er en kort diskussion af dette forhold udtrykt som selektivitetsfaktorer meningsfyldt. Det er sædvanligvis onsk-værdigt, at afgrodesikkerhedsfaktorerne, dvs. herbicide to-'20 leranceværdier, er hoje, fordi man af en eller grund hyp-pigt onsker hojere herbicidkoncentrationer. Det er omvendt onskværdigt, at pâforingsintensiteterne med henblik pâ kontrol af ukrudt er smâ, altsâ at der foreligger en hoj enhedsaktivitet af herbicidet af hensyn til okonomiske og 25 muligvis okologiske ârsager. Imidlertid er smâ pâforings- intensiteter af et herbicid ikke nodvendigvis tilstrækkelige til at kontrollere visse ukrudtsarter, og en storre pâfo-ringsintensitet kan være nodvendig. De bedste herbicider er sâledes sâdanne, som kontrollerer det storste antal af 50 ukrudtsarter med den mindste mængde herbicid og tilvejebrin-ger den storste grad af afgrode s ikkerhed, dvs. afgrode-tolerance. Man gor som folge deraf brug af "selektivitetsfaktorer" (i henhold til den ovenfor angivne définition) for at kvantificere forholdet mellem afgrodesikkerhed og 35 ukrudtskontrol. Med henblik pâ de selektivitetsfaktorer,Since crop tolerance and weed control are interdependent, a brief discussion of this relationship expressed as selectivity factors is meaningful. It is usually desirable that the crop security factors, ie. herbicide two-'20 lerance values, are high because for some reason, higher herbicide concentrations are desired. On the contrary, it is undesirable that the application intensities for the control of weeds are small, so that there is a high unit activity of the herbicide for economic and possibly ecological reasons. However, small application intensities of a herbicide may not be sufficient to control certain weed species and greater application intensity may be necessary. Thus, the best herbicides are those which control the largest number of 50 weed species with the least amount of herbicide and provide the highest degree of crop safety, ie. afgrode-tolerance. As a result, "selectivity factors" (according to the above definition) are used to quantify the relationship between crop security and weed control. In view of the selectivity factors,

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23 der er angivet i tabellerne, kan det an-fores, at jo stor-re den numeriske værdi er, desto hojere er selektiviteten af herbicidet for ukrudtskontrol i en given afgrode.23 indicated in the tables, it may be stated that the greater the numerical value, the higher the selectivity of the herbicide for weed control in a given crop.

For at illustrere de overlegne egenskaber af forbindel-5 serne ifolge opfindelsen, bâde pâ absolut og relativ ba~ sis, gennemforte man komparative forsog i drivhus med kendte forbindelser, der var mest beslægtet med forbin-delserne ifolge opfindelsen, hvad angâr kemisk struktur.To illustrate the superior properties of the compounds of the invention, both on absolute and relative basis, comparative tests were carried out in greenhouses with known compounds most closely related to the compounds of the invention as regards chemical structure.

Disse forbindelser, der er kendt fra BE patentskrift nr.These compounds, known from BE patent specification no.

10 810 763, hvortil der tidligere har været henvist, er i- dentificeret pâ folgende mâde (under anvendelse af den samme nomenklatur soin for forbindelserne ifelge opfindelsen) : A. N-(methoxyethyl)-2'-trifluormethyl-2-chloracetanilid 15 B. N-(ethoxyethÿl)-2'-trifiluormethyl-2-chloracetanilid I tabel IV og V præsenteres der data for herbicid aktivi-tet for spiringen, hvorved man sammenligner den relative effektivitet af forbindelserne ifolge opfindelsen og af de kendte forbindelser som selektive herbicider mod de 20 resistente og besværlige flerârige ukrudtsplanter, sâsom kvikgræs og gui "nutsedge" i henholdsvis sojabonner og majs. Disse ukrudtsplanter er sædvanligvis associeret med sâdanne storre afgroder som majs og sojabonner. De i tabellerne IV og V angivne forsogsdata fremkom under iden-25 tiske betingelser og repraesenterer gennemsnittet af to gentagne forsog (med undtagelse af forbindelsen fra eks-empel 13, der var til stede ved et komparativt forsog). Forsogsmetoden var den samme som beskrevet for tabellerne Il og III, men modificeret ved anvendelsen af en ini-30 tial, kunstig vanding, der kommer ovenfra, ækvivalent med 0,64 cm regnfald; pâfolgende vanding blev gennemfort ved nedefra kommende, kunstig vanding. "NS" betyder ikke se-lektiv indenfor disse forsogsgraenser.No. 10,810,763, to which reference has previously been made, is identified as follows (using the same nomenclature for the compounds of the invention): A. N- (methoxyethyl) -2'-trifluoromethyl-2-chloroacetanilide 15 B N- (Ethoxyethyl) -2'-trifiluoromethyl-2-chloroacetanilide Tables IV and V present data on the herbicide activity of the germination, comparing the relative efficacy of the compounds of the invention with the known compounds as selective herbicides against the 20 resistant and troublesome perennial weeds, such as quick grass and gui "nutsedge" in soybeans and maize respectively. These weeds are usually associated with such larger crops as maize and soybeans. The test data set forth in Tables IV and V were obtained under identical conditions and represent the average of two repeated tests (with the exception of the compound of Example 13 present in a comparative test). The experimental method was the same as described for Tables II and III, but modified by the use of an initial artificial irrigation coming from above, equivalent to 0.64 cm of rainfall; Subsequent irrigation was carried out by downward artificial irrigation. "NS" does not mean selective within these experimental limits.

2424

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TABEL IVTABLE IV

Forbin- GR.-pâforings- GRocPâfe^ÏHÇfsiHtensitet, delse intensitet, kq/ha _kg/ha__Connecting GR.-applying GRocPåfe ^ ÇHighsensitivity, intensity, kq / ha _kg / ha__

Sojab0nner_ Kvikgraes Gui "nutsedge” A > 2,24 >2,39(NS) 1,13(1,98) B 1,96 0,61(3,21) 0,44(4,45) eks. 1 2,67 0,17(15,6) 0,17(15,6) eks. 3 1,68 0,27(6,22) 0,19(8,84) eks. 4 1,12 0,13(8,62) 0,17(6,59) eks. 5 1,46 0,26(5,62) 0,26(5,62) eks. 13 2,13 0,20(10,65) 0,17(12,53)Soybean_ QuickGuy Gui "nutsedge" A> 2.24> 2.39 (NS) 1.13 (1.98) B 1.96 0.61 (3.21) 0.44 (4.45) EX 1 2 , 67 0.17 (15.6) 0.17 (15.6) EX 3 1.68 0.27 (6.22) 0.19 (8.84) EX 4 1.12 0.13 ( 8.62) 0.17 (6.59) Ex 5 1.46 0.26 (5.62) 0.26 (5.62) Ex 13 2.13 0.20 (10.65) 0, 17 (12.53)

Idet der henvises til de i tabel IV angivne data, vil man se, at enhver af forbindelserne ifolge opfindelsen- udvi-ste meget hojere selektivitetsfaktorer (værdier i parentes) mod bâde kvikgraes og gui "nutsedge" i sojabbnner 5 end de kendte forbindelser. Især bemærkes, at enhedsak-tiviteterne (den relative phytoxicitet pr. enhed af her-bicid) af forbindelserne ifolge opfindelsen er betydeligt hojere mod kvikgraes og gui "nutsedge" end for de kendte forbindelsers vedkommende, mens man bibeholder afgrode-10 sikkerheden. Man bemærker især de fremragende hoje selektivitetsfaktorer af forbindelserne i henhold til eksempel 1 og 13.Referring to the data set forth in Table IV, it will be seen that each of the compounds of the invention exhibited much higher selectivity factors (values in brackets) against both quick grass and gui nutsedge in soybeans 5 than the known compounds. In particular, it is noted that the unit activities (the relative phytoxicity per unit of herbicide) of the compounds of the invention are significantly higher against mercury and gui "nutsedge" than for the known compounds while maintaining the crop protection. Notably, the excellent high selectivity factors of the compounds of Examples 1 and 13 are noted.

Yderligere komparative data, der viser den relative effek-tivitet af forbindelser ifolge opfindelsen i sammenligning 15 med de ovenfor angivne, kendte forbindelser mod kvikgræs og gui "nutsedge" i majs, er prasenteret i tabel V.Further comparative data showing the relative effectiveness of compounds of the invention in Comparison 15 with the above-mentioned known compounds against mercury and gui "nutsedge" in maize are presented in Table V.

25 DK 157189 BDK 157189 B

TABEL VTABLE V

riàflintin- GR85 Pff^ingsintensitet sitet (kq/ha)-iMMl-riàflintin- GR85 Pffing intensity site (kq / ha) -iMMl-

Forbindelse -mais_ Kvikgræs gui "nutsedge" A >2,24 >2^ 39 (NS} 1,13(1,92) 8 0,81 0/51 (1,33) 0,44 (1,84)Compound-maize_ Mercury grass gui "nutsedge" A> 2.24> 2 ^ 39 (NS) 1.13 (1.92) 8 0.81 0/51 (1.33) 0.44 (1.84)

Eksempel 1 0,7o 0,17(4,4?) 0,17(4,47) » 3 1,94 0,27 (7,19) 0,19 (10,2) « 4 0,75 0,13(5,85) 0,17(4,47) " 5 lf33 ^ 0,25(7,04) 0,25(7,04) " 13 2,24 0,20(11,2) 0,17(13,18)Example 1 0.7 0.17 (4.4?) 0.17 (4.47) »3.94 0.27 (7.19) 0.19 (10.2) 13 (5.85) 0.17 (4.47) "5f33 ^ 0.25 (7.04) 0.25 (7.04)" 13 2.24 0.20 (11.2) 0.17 (13.18)

Idet der henvises til de i tabel V angivne værdier, vil det be-mærkes, at enhver af forbindelserne if0lge opfindelsen ud-viste langt hojere selektivitetsfaktorer mod bâde kvikgræs og gui "nutsedge" i majs end de kendte forbindelser. Igen be-5 mærkes det, at enhedsaktiviteter af forbindelserne if0lge opfindelsen var betydeligt hojere mod kvikgræs og gui "nutsedge " end for de kendte forbindelsers vedkommende, mens afgrodesikkerheden blev opretholdt. Man lægger især mærke til de store selektivitetsfaktorer for forbindelserne fra 10 eksemplerne 3, 5 og 13, især i sammenligning med selektivi-tetsfaktorerne for de kendte forbindelser.Referring to the values given in Table V, it will be appreciated that each of the compounds of the invention exhibited far higher selectivity factors against both mercury and yellow corn seed than the known compounds. Again, it is noted that unit activities of the compounds of the invention were significantly higher against mercury and gui "nutsedge" than for the known compounds while maintaining crop security. Particular attention is paid to the large selectivity factors for the compounds of Examples 3, 5 and 13, especially in comparison with the selectivity factors for the known compounds.

Pâ basis af de komparative data, der er vist i tabel IV og V, er det klart, at forbindelserne if0lge opfindelsen ud-viste fremragende hojere og uventet overlegen herbicid 15 effektivitet mod de i herbicid henseende resistente, fler-ârige ukrudtsarter kvikgræs og gui "nutsedge" i to hovedaf-groder, nemlig sojabonner og majs, end forbindelserne A og B, der er de kendte forbindelser, der er mest beslægtet dermed.Based on the comparative data shown in Tables IV and V, it is clear that the compounds of the invention exhibited excellent higher and unexpectedly superior herbicide efficacy against the herbicide resistant, perennial weed species of mercury and gui. nutsedge "in two main crops, namely soybeans and corn, than compounds A and B, which are the known compounds most closely related to it.

Hertil kommer, at herbicide data f0r spiringen fra andre for-•20 S0g har vist, at forbindelser ifolge opfindelsen ogsâ pâ se-lektiv mâde kontrollerer kvikgræs, gui "nutsedge" og/eller 26In addition, herbicidal data for germination from other experiments have shown that compounds of the invention also selectively control mercury, gui "nutsedge" and / or 26

DK 157189 BDK 157189 B

andre ukrudtsarter i en eller flere af afgraderne bomuld, jordnodder, krybbonner, hvede, sorghum og/eller raps. I tabel VI er der f. eks. præsenteret data, der viser den herbicide effektivitet af forbindelserne i eksempel 1 og 3 5 mod kvikgræs i raps, brydbonner, sorghum og hvede. Med min- dre andet er angivet, involverede drivhusforsogene i tabel VI og i andre tabeller i det folgende herbicide behandlinger ved inkorporering i jord og en initial, ovenfra kommende kun-stig vanding efterfulgt af en nedefra kommende, kunstig van-10 ding som beskrevet det foregâende.other weed species in one or more of the grades of cotton, peanuts, creepers, wheat, sorghum and / or rapeseed. For example, Table VI presents data showing the herbicidal efficacy of the compounds of Examples 1 and 35 against mercury in rapeseed, groundnuts, sorghum and wheat. Unless otherwise indicated, the greenhouse trials in Table VI and in other tables in the following herbicidal treatments involved soil incorporation and an initial, above-ground, only-stage irrigation, followed by a downward artificial habitat as described above. preceding.

TABEL VITABLE VI

GR-,pâforingsintensitet GRoc pâf.int. (kg/ha ) ^ (kg/ha) -22-GR, applied intensity GRoc applied. (kg / ha) 2 (kg / ha) -22-

Forbindelse Raps BrydbonnerSorghum Hvede KvikgræsConnection rapeseed beansSorghum wheat Mercury

Eks. 1 - - 0,12(7,2) ii - 0,90 - - 0,12(7,5) 0,24 - 0,12(2,0) - - 0,21 0,12(1,5) » 3 1,9 - - - 0*23(6,3) 2,24 - - 0,23(3,0) 0,34 - 0,23(3,0) - - 0,23 0,23(1,0)Ex. 1 - 0.12 (7.2) ii - 0.90 - 0.12 (7.5) 0.24 - 0.12 (2.0) - 0.21 0.12 (1.5 ) »3 1.9 - - - 0 * 23 (6.3) 2.24 - - 0.23 (3.0) 0.34 - 0.23 (3.0) - - 0.23 0.23 (1.0)

Forbindelsen fra eksempel 1 blev ogsâ undersogt i marken for at bestemme dens selektivitet for spiringen· mod ræveha-le (spp), hanespore og hvid proso-hirse i mange forskellige afgroder; de pâgældende data (der repræsenterer *tre gentagne 15 forscg) er vist i tabel VII bàde for overfladepâforing (S.A) og for inkorporering· i jord (P.P.I., dvs. inkorporering for sâning) af herbicidet. Froene blev sâet i et fint sâbed af lerdynd med middelhoj fugtighed. Froene blev sâet i en dybde af 5,08 cm. Forste regnfald (0,51 cm) forekom dagen efter be-20 handlingen, og det andet regnfald (0,64 cm) forekom to dage efter behandlingen; det kumulative regnfald 22 dage efter behandlingen var 4,57 cm. Man gjorde observationer 5 uger efter behandlingen.The compound of Example 1 was also examined in the field to determine its selectivity for germination against foxhole (spp), male spore and white prose millet in many different crops; the data in question (representing * three repetitive studies) are shown in Table VII both for surface application (S.A) and for soil incorporation (P.P.I., i.e., sowing incorporation) of the herbicide. The seeds were sown in a fine seed of medium-high humidity. The seeds were sown at a depth of 5.08 cm. First rainfall (0.51 cm) occurred the day after the treatment, and the second rainfall (0.64 cm) occurred two days after the treatment; the cumulative rainfall 22 days after treatment was 4.57 cm. Observations were made 5 weeks after treatment.

2727

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2828

De i tabel VII angivne data viser, at forbindelsen fra eksempel 1 sædvanligvis udviste bedre egenskaber som se-lektivt herbicid pâfort ved overfladepâforing end, nâr det blev inkorporeret i jorden. Især kontrollerede herbi-5 cidet de tre ukrudtsarter selektivt i forsoget ved pâfo-ringsintensiteter over 0,58 kg/ha, mens man bibeholdt af-grodesikkerheden (dvs. op til en maksimal beskadigelse pâ ca. 15%) i markmajs og sojabonner op til 4,48 kg/ha i sod majs, jordnodder og raps ved over 2,24 kg/ham og i 10 bomuld, sorghum og krybbonner ved pâforingsintensiteter netop under 2,24 kg/ha. Ved P.P.I.-forsogene kontrollerede forbindelsen fra eksempel 1 selektivt rævehalear-terne og hanespore ved pâforingsintensiteter pâ under 1,12 kg/ha, mens man bibeholdt afgrodesikkerhed i mark-15 majs, jordnodder og raps ved pâforingsintensiteter op til 2,24 kg/ha og lidt under 2,24 kg/ha for sojabonner.The data set forth in Table VII shows that the compound of Example 1 usually exhibited better properties as selective herbicide applied to surface application than when incorporated into the soil. In particular, the herbicide selectively controlled the three weed species in the test at application intensities above 0.58 kg / ha while maintaining crop safety (ie up to a maximum damage of about 15%) in field maize and soybeans up to 4.48 kg / ha in soot corn, peanuts and rapeseed at over 2.24 kg / ha and in 10 cotton, sorghum and creepers at application intensities just below 2.24 kg / ha. For the PPI pretreatments, the compound of Example 1 selectively controlled the fox tail species and male spores at application intensities below 1.12 kg / ha, while maintaining crop security in field maize, groundnuts and rapeseed at application intensities up to 2.24 kg / ha and slightly below 2.24 kg / ha for soybeans.

André data for markprover for forbindelsen fra eksempel 1 viste selektiv kontrol for spiringen af andre ukrudts-planter i majs, sojabonner, bomuld og/eller jordnodder, 20 sâsom purpur "nutsedge", kæmperævehale, gui rævehale, hvidmelet gâsefod, ipomoea, brodfro, flojlsblad, Pennsylvania vandpeber, tornet sida, portulak, fingeraks, gâse-græs, Texas panicum·, Florida portulak og/el'ler stikkende "starbur". Det vil forstâs af sagkyndige, at ikke aile 25 af de navngivne ukrudtsarter kontrolleres selektivt i aile de angivne afgroder under aile betingelser hvad an-gàr klima, jordbund," fugtighed og/eller herbicid pâfo-ringsmetode. Selektivitetsdata for kontrol af de i det fpregâende angivne ukrudtsplanter i afgroderne sojabon-30 ner, majs, bomuld og jordnodder pâ basis af et storre an-tal markprover i forskellige lokaliteter under forskel-lige betingelser hvad angâr jordbund, fugtighed, osv. vises kollektivt i tabellerne VIII - XI. I tabellerne be-tyder "WAT" uger efter behandling" af planterne med her-35 bicidet, pâfort enten ved overfladepâforing ("S.A.") el-Other field test data for the compound of Example 1 showed selective control for germination of other weeds in corn, soybeans, cotton and / or peanuts, such as purple "nutsedge", giant fox tail, gui fox tail, white flour goose foot, ipomoea, brood leaf , Pennsylvania pepper, thorny side, portulak, fingerax, geese-grass, Texas panicum ·, Florida portulak and / or stinging "starbur". It will be understood by experts that not all 25 of the named weed species are selectively controlled in all the specified crops under all conditions of climate, soil, moisture and / or herbicide application method. Selectivity data for control of the aforementioned indicated weeds in the crops soybeans, maize, cotton and peanuts on the basis of a larger number of field samples in different localities under different conditions regarding soil, moisture, etc. are collectively shown in Tables VIII - XI. - indicates "WAT" weeks after treatment "of the plants with herbicide, applied either by surface application (" SA ") or-

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29 1er ved inkorporering i jorden for sâningen ("P.P.I."); data for pâforingsintensiteten for hver kombination af-grode/ukrudt vises i form af værdier for GR^,.- °9 ^R85~ pâforingsintensiteterne (defineret i det foregâende); 5 hvorved forholdet GR1ir/GR0i- resulterer i selektivitets- 15 05 faktoren, "S.F."; "NS" betyder ikke-selektivitet, og en bindestreg (-) betyder marginal eller ubesteimnelig selek-tivitet, f.eks. fordi faktiske GR-^- og GRg^-pâforingsin-tensiteter var hojere eller lavere end de maksimale eller 10 minimale pâforingsintensiteter, der anvendes i det angiv-ne forsog. I tabellerne VIII - XI betyder et tomt rum, at plantearten ikke forelâ i noget særligt forsogsareal eller at de foreliggende data ikke var opnâet eller var mindre signifikante end andre af de præsenterede data, f.29 1 by incorporation into the soil for sowing ("P.P.I."); the application intensity data for each crop / weed combination is shown in the form of values for GR ^, - 9 ° R85 ~ application intensities (defined above); 5 whereby the ratio GR1 / GR01 results in the selectivity factor, "S.F."; "NS" means non-selectivity, and a dash (-) means marginal or indeterminate selectivity, e.g. because the actual GR - ^ and GRg ^ application intensities were higher or lower than the maximum or minimum application intensities used in the test. In Tables VIII - XI, an empty space means that the plant species did not exist in any particular experimental area or that the available data were not obtained or were less significant than any of the data presented, f.

15 eks. var nogle 3 WAT-observationer udeladt til fordel for 6 WAT-data, eller 6 WAT-data var udeladt, fordi 3 WAT-data var definitive.For example, some 3 WAT observations were omitted in favor of 6 WAT data, or 6 WAT data were omitted because 3 WAT data were definitive.

TABEL VIIITABLE VIII

Pâf0- ..Pâf0- ..

Forbin- Afgrode/ukrudt rings- delse kombination met ode»,gr, /gr s.F.Combine Crop / weed ring combination with ode », gr, / gr s.F.

Eks. 1 sojabonner s.a. 3 kæmperæveha- 5 >4,48/<i,i2 (>4,P) le P.P.I. 3 5 >4,43/<l,12 (>4,0> 3 >4,48/<l,12 (>4,Q) sojabonner, s. a. . 5 2,52/2,3 (ns) P.P.I. ^ 01.31 sojabonner, s.A. ·*· 2,52/2,52 (1,0) hvidmelet gâsefod P.P.I. 5 1,4/2,* MS) sojabonner, P.P.I. 3 4,43/2,52 (1,2)Ex. 1 soybeans s.a. 3 Giants fox- 5> 4.48 / <i, i2 (> 4, P) le P.P.I. 3 5> 4.43 / <l, 12 (> 4.0> 3> 4.48 / <l, 12 (> 4, Q) soybeans, so 2.52 / 2.3 (ns) PPI 01.31 soybeans, sA · * · 2.52 / 2.52 (1.0) white flour goose foot PPI 5 1.4 / 2, * MS) soybeans, PPI 4.43 / 2.52 (1.2)

Pennsylvania ' vandpeberThe pepper of Pennsylvania

' DK 157189B'DK 157189B

3030

De i tabel VIII angivne data viser, at forbindelsen fra eksempel 1 selektivt kontrollerede keemperævehale og gui rævehale, hvidmelet gâsefod og Pennsylvania vandpeber i sojabonner fra 6-8 WAT enten ved pâforingsmetoden S.A. eller P.P.I.The data set forth in Table VIII shows that the compound of Example 1 selectively controlled beetle tail and gui fox tail, white flour goose foot and Pennsylvania water pepper in soybeans from 6-8 WAT either by the method of application S.A. or P.P.I.

TABEL IXTABLE IX

Pâfo-Pâfo-

Porbin- Afgrode/ukrudt rings- .Porbin- Crop / weed ring.

delse kombination metode WAT K15/ K85 S,F. ,partition combination method WAT K15 / K85 S, F. .

Eks. 1 majs, kasmpe- S.A. 6 4,48/<l,12 (4,0) rævehale S.A. 6,5 >7,84/8,4 (NS) P.P.I. 6 4,76/1,96 (2,5) P.P.I. 6,5 >6,72/4,48 (1,5) majs, ipomoea S.A. 3 >4,48/>4,48 ( - ) S.A. 6 >4,48/>4,48 ( - ) P.P.I. 3 4,76/>4,43 ( - ) P.P.I. 6 4,76/>4.,48 ( - ) majs, brod- S.A. 3 >4,48/>4,48 ( - ) fro S.A. 6 >4,48/>4,48 ( - ) P.P.I. . 3 4,76/>4,48 ( - ) P.P.I. 6 4,76/>4,48 ( - )Ex. 1 corn, kasmpe- S.A. 6 4.48 / <l, 12 (4.0) fox tail S.A. 6.5> 7.84 / 8.4 (NS) P.P.I. 6 4.76 / 1.96 (2.5) P.P.I. 6.5> 6.72 / 4.48 (1.5) corn, ipomoea S.A. 3> 4.48 /> 4.48 (-) S.A. 6> 4.48 /> 4.48 (-) P.P.I. 3 4.76 /> 4.43 (-) P.P.I. 6 4.76 / 4., 48 (-) corn, brod- S.A. 3> 4.48 /> 4.48 (-) fro S.A. 6> 4.48 /> 4.48 (-) P.P.I. . 3 4.76 /> 4.48 (-) P.P.I. 6 4.76 /> 4.48 (-)

De i tabel IX angivne data viser, at forbindelsen fra eksempel 1 selektivt kontrollerede kæmperævehale i majs fra 6-6,5 WAT enten ved pâforingsmetoden S.A. eller P.P.I.; selektivitet af ipomoea og brodfro var ikke be-stemt ved pâforingsintensiteterne under forsoget, men disse ukrudtsarter blev undertrykt.The data in Table IX shows that the compound of Example 1 selectively controlled giant fox tail in maize from 6-6.5 WAT either by application method S.A. or P.P.I .; selectivity of ipomoea and brood seed was not determined by the application intensities during the experiment, but these weed species were suppressed.

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TABEL X Pâf0-TABLE X Páf0-

Forbin- Afgrode/ukrudt rings- del se kombination met ode Süi 5/-3 5 —Combine - Crop / weed ring part see combination with ode Süi 5 / -3 5 -

Eks. 1 bomuld, purpur S*A* ^ "nutsedge" S. A. 9 3, 3o/2,2< d,-) P.P.I. 6 · 3,38/4,2 (NS) bomuld, tornet s.a. 8' 3.64/3.03 d,i8) sida S. A. 9 3,36/4,7-5 (NS) P.P.I. 6 3,35/4,76 MS) bomuld, por- S.A. 9 3,36/1,96 (1,7) tulak bomuld,finger- S.A. 7 1,4/<1,12 (>1,25) aks (glat Og P.P.I. 7 0,84/1,12 MS) bomuld, gâse- P.P.I. 7 0,84/<l,12 ( - ) fodEx. 1 cotton, purple S * A * ^ "nutsedge" S. A. 9 3, 3o / 2.2 <d, -) P.P.I. 6 · 3.38 / 4.2 (NS) cotton, turret s.a. 8 '3.64 / 3.03 d, i8) Page S. A. 9 3.36 / 4.7-5 (NS) P.P.I. 6 3.35 / 4.76 MS) cotton, por- S.A. 9 3.36 / 1.96 (1.7) tulak cotton, finger- S.A. 7 1.4 / <1.12 (> 1.25) axis (smooth And P.P.I. 7 0.84 / 1.12 MS) cotton, geese- P.P.I. 7 0.84 / l, 12 (-) feet

De i tabel X angivne data viser, at forbindelsen fra eksem-pel 1 pâ selektiv mâde kontrollerede purpur "nutsedge" og portulak op til 9 WAT, tornet sida op til 6 ¥AT og fin-geraks op til 7 WAT; kontrollen af gâsegræs var marginal 5 eller ubestemmelig.The data set forth in Table X show that the compound of Example 1 selectively controlled purple "nutsedge" and porcelain up to 9 WAT, thorny side up to 6 ¥ AT, and fine-grained up to 7 WAT; the control of geese grass was margin 5 or indeterminate.

I tabel XI er der repræsenteret data for aktivitet for spiringen for forbindelsen fra eksempel 1 mod tre resisten-te, etârige ukrudtsarter, nemlig Texas panicum, stikkende "starbur" og Florida portulak i jordnodder i perioder 10 op til 12 WAT. De i tabel XI angivne data repræsenterer gennemsnittet af tre gentagne forsog i sandet lerdynd med et indbold af organisk materiale pâ 1,3%, 79,3% sand og 10% 1er; herbicidet blev pâfort pâ overfladen.Table XI represents germination activity data for the compound of Example 1 against three resistant, annual weed species, namely Texas panicum, stinging "starbur" and Florida groundnuts in periods 10 up to 12 WAT. The data given in Table XI represent the average of three repeated attempts in sandy clay with an organic matter yield of 1.3%, 79.3% sand and 10% 1er; the herbicide was applied to the surface.

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En henvisning til de i tabel XI angivne data viser, at for-bindelsen fra eksempel 1 selektivt kontrollerede Texas panicum i jordnodder i op til 8 uger, og at den tilveje-bragte en hoj grad af kontrol, selv ved 12 ¥AT ved ca.A reference to the data set forth in Table XI shows that the compound of Example 1 selectively controlled Texas panicum in groundnuts for up to 8 weeks, and provided a high degree of control, even at 12 µ AT at ca.

5 4,43 kg/ha; selektiv kontrol af stikkende "starbur" blev . .4.43 kg / ha; selective control of prickly "starbur" became. .

opnâet ved 3,36 kg/ha i 8 uger, og fuldstændig kontrol blev bibeholdt i 12 WAT ved 4,48 kg/ha, og selektiv kontrol med Florida portulak blev opnâet med under 2,24 kg/ha ved 8 WAT, og med 4,48 kg/ha opnâedes 95% kontrol ved 12 WAT.achieved at 3.36 kg / ha for 8 weeks, and complete control was maintained at 12 WAT at 4.48 kg / ha, and selective control of Florida portulas was achieved at less than 2.24 kg / ha at 8 WAT, and with 4.48 kg / ha 95% control was obtained at 12 WAT.

10 Ved andre drivhusforsog har forbindelser ifolge opfindelsen vist selektiv kontrol med mange forskellige etârige og flerârige ukrudtsarter i forskellige afgroder. Som en yderligere illustration kan det anfores, at forbindelsen i eksempel 1 pâ-selektiv mâde kontrollerede purpur "nut---15 sedge" i bàde majs og sojabonner, idet de pâgældende for-hold GR^/GRq^ for afgrode/ukrudt (udtrykt i kg/ha) var 0,67/0,25 (S.F. = 2,7) i majs og 1,12/0,25 (S.F. = 4,5) i sojabonner. Forbindelsen fra eksempel 11 har udvist selektiv kontrol af gui "nutsedge” og kvikgræs i 20 majs og sojabonner. De pâgældende forhold GR-^/GRg^ for afgrode/gul "nutsedge" er >2,24/0,9.5 (S.F. = 2,4) i majs; 2,24-/0,5 (SF = 4,5) i sojabonner, og de pâgældende forhold GRi^/GRg^ for bâde majs og sojabonner i kvikgræs er >2,24/ 0,5 (S.F. = >4,5). I en prove xnod gui "nutsedge" i bomuld 25 var f°rholdet GRy,-/GRgi- (gennemsnit af to gentagne forsog) 1,96/0,95 (S.F. = 2,1). Pâ lignende mâde udviste forbindelsen fra eksempel 13 selektiv kontrol med gui "nutsedge" i bomuld og af kvikgræs i hvede, idet de pâgældende for-hôld GR^/Gr^_ var 0,7/0t47 (S.F. = 1,7) i bomuld og 30 0,58/0,47 (S.F. = 1,2) i hvede.10 In other greenhouse trials, compounds of the invention have shown selective control of many different annual and perennial weed species in different crops. As a further illustration, it can be stated that the compound of Example 1 selectively controlled purple "nut --- sedge" in both corn and soybeans, with the applicable ratios GR ^ / GRq ^ for crop / weeds (expressed in kg / ha) was 0.67 / 0.25 (SF = 2.7) in maize and 1.12 / 0.25 (SF = 4.5) in soybeans. The compound of Example 11 showed selective control of gui "nutsedge" and mercury in 20 corn and soybeans. The ratios GR - ^ / GRg ^ for crop / yellow "nutsedge" are> 2.24 / 0.9.5 (SF = 2 (4) in maize; 2.24- / 0.5 (SF = 4.5) in soybeans and the ratios GRi ^ / GRg ^ for both maize and soybeans in mercury are> 2.24 / 0.5 ( SF => 4.5) In a sample of cotton "nutsedge" in cotton 25 the ratio GRy, - / GRgi (average of two repeated attempts) was 1.96 / 0.95 (SF = 2.1) Similarly, the compound of Example 13 exhibited selective control of gui "nutsedge" in cotton and of mercury in wheat, with the ratios GR ^ / Gr ^ _ being 0.7 / 0t47 (SF = 1.7). cotton and 0.58 / 0.47 (SF = 1.2) in wheat.

Ved et forsog med mange afgroder i drivhus blev forbindel-serne fra eksempleme 1, 13, 14 og 15 undersogt mod gui "nutsedge" i bomuld, sojabonner, majs og ris; hver forbin-delse var ikke selektiv, hvad angâr gui "nutsedge" i ris.In an experiment with many crops in greenhouses, the compounds of Examples 1, 13, 14 and 15 were tested against gui "nutsedge" in cotton, soybeans, corn and rice; each compound was not selective in terms of gui "nutsedge" in rice.

35 Imidlertid pâvistes bemærkelsesværdigt hoje selektiviteter35 However, remarkably high selectivities were demonstrated

DK 157189 BDK 157189 B

34 for gui "nutsedge" i bomuld, sojabonner og majs for hver af forbindelserne i forsoget; de pâgældende GR·^ og GRQ^ pàforingsintensiteter for disse forbindelser er vist i ta-bel XII; selektivitetsfaktorer er vist i parentes efter 5 hver afgrode.34 for gui "nutsedge" in cotton, soybeans and corn for each of the compounds in the test; the applied GR ^ and GRQ p application intensities for these compounds are shown in Table XII; selectivity factors are shown in parentheses after 5 each crop.

DK 157189 BDK 157189 B

3535

TABEL XIITABLE XII

Forbin- GR15(kg/ha) ' GRo,- (kg/ha)Compound GR15 (kg / ha) 'GRo, - (kg / ha)

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fra_"nutsedge1' uld sojabonner majs eks. 1 0,24 1,95( 3r2) 0,.87(3,1} 0,1-3( 2,3) » 13 0, 21 2,52 (12,0) 1,95(9,3) 2,52(12,0) » 14 0,33 2,3 ( 7,4) 2,24 (5,9) 1,53 ( 4,4) » 15 0,44 2,8 ( -5,4) 1,95 (4,5) 1,9-5 ( 4,5)from_ "nutsedge1" wool soybean corn ex 1 0.24 1.95 (3r2) 0.87 (3.1} 0.1-3 (2.3) »13 0, 21 2.52 (12.0 ) 1.95 (9.3) 2.52 (12.0) »14 0.33 2.3 (7.4) 2.24 (5.9) 1.53 (4.4)» 15 0, 44 2.8 (-5.4) 1.95 (4.5) 1.9-5 (4.5)

Forbindelserne fra eksempel 1 og 13 - 15 blev yderligere unders0gt mod kvikgræs i hvede, sojabonner og ma^jsj det vi-ste sig, at hver forbindelse var ikke selektiv i hvede. Se-lektivitetsdata for de ovenfor angivne forbindelser mod 5 kvikgræs i sojabonner og majs er vist i tabel XIII.The compounds of Examples 1 and 13 - 15 were further investigated against mercury in wheat, soybeans and maize, knowing that each compound was not selective in wheat. The selectivity data for the above compounds against 5 mercury in soybeans and maize are shown in Table XIII.

TABEL XIIITABLE XIII

Gr85 ®isGr85 ® is

Forbin- (kg/ha) (kg/ha) (4p 1 c 0 kvikgræs sojabonner majs eks. I 0,07 0,01(11,5} 0,59(9,9} ir 13 0,36 1,58( 4.7) 1,53(4,7) " 14 0,45 1,45 ( 3,2) 2,52 (5, 5} " 15 q,75 1,95 ( 2,5) 2,24(3,0) et yderligere drivhusfors0g til bestemmelse af herbicid effektivitet undersogte man forbindelserne fra eksempel 1 og 3 mod et antal etârige græsser, herunder resistente ukrudtsarter, sâsom Texas panicum, durra-kimplante, "shat-10 tercane”, alexandergræs, vild proso-hirse (panicum mili-caeum), rod-ris og klogræs. Resulaterne af disse forsog er vist i tabel XIV· selektivitetsfaktorer er angivet i parentes, hvorved en bindestreg viser marginal eller ikke bestemt selektivitet.Combine (kg / ha) (kg / ha) (4p 1 c 0 mercury soybean corn excl. I 0.07 0.01 (11.5} 0.59 (9.9} ir 13 0.36 1.58 (4.7) 1.53 (4.7) "14 0.45 1.45 (3.2) 2.52 (5.5)" 15 q, 75 1.95 (2.5) 2.24 (3) , 0) a further greenhouse trial to determine herbicide efficacy investigated the compounds of Examples 1 and 3 against a number of annual grasses, including resistant weeds, such as Texas panicum, sorghum, shat-tercane, alexander grass, wild prose millet (panicum mili-caeum), root rice and clover grass. The results of these experiments are shown in Table XIV. Selectivity factors are indicated in brackets whereby a dash indicates marginal or undetermined selectivity.

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De i tabel XIV angivne data viser*: at forbindelsen i henhold til eksempel 1 selektivt kontrollerede ethvert etârigt ukrudt i forsoget i sojabonner. Forbindelsen fra eksempel 3 udviste positiv, selektiv kontrol mod 5 aile ukrudtsar't'er, med undtagelse af Texas panicum, vild proso-hirse og klogræs ved den maksimale pâforingsinten-sitet under forsoget pâ 1,12 kg/ha; man ville hâve kræ-vet en hojere pâforingsintensitet for at bestemme selek-tivitet af forbindelsen mod de tre ukrudtsarter, der 10 ikke udviste selektiv kontrol ved pâforingsintensiteten under forsoget.The data in Table XIV show *: that the compound of Example 1 selectively controlled any one-year weed in the soybean test. The compound of Example 3 exhibited positive selective control against 5 all weed species, with the exception of Texas panicum, wild prose millet and clover grass at the maximum application intensity during the experiment of 1.12 kg / ha; a higher application intensity would be required to determine the selectivity of the compound against the three weed species that did not exhibit selective control at the application intensity during the test.

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En tydelig fordel ved et herbicid er dets evne til at fungere i mange forskellige jordtyper. Sont folge deraf er der i tabel XV præsenteret data, der viser den herbi-15 eide virkning af forbindelsen fra eksempel 1 pâ kvikgræs i sojabonner i mange forskellige jordtyper med varieren-de indhold af organisk materiale og 1er. De herbicide behandlinger blev gennemfort ved inkorporering i jorden med fro, der er saet” i en dybde af 0,95 cm og med en 20 kunstig vanding ovenfra pâ 0,64 cm. Man gjorde sine iagt-tagelser ca. 3 uger efter behandlingen. Selektivitets-faktorer er vist i parentes.A distinct advantage of a herbicide is its ability to function in many different soil types. Consequently, data are presented in Table XV showing the herbicidal effect of the compound of Example 1 on mercury in soybeans in many different soil types with varying organic matter content and 1s. The herbicidal treatments were carried out by incorporation into the soil with seeds sown ”at a depth of 0.95 cm and with an artificial top irrigation of 0.64 cm. You made your observations about. 3 weeks after treatment. Selectivity factors are shown in parentheses.

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De i tabel XV angivne data viser, at forbindelsen fra eksempel 1 viser sig at være ret ufolsom overfor jord-bundstyper med varierende indhold af organisk materiale, idet den udviser selektiv kontrol med kvikgræs i sojabon-5 ner i jord, der spænder mellem 1,0 og 60% organisk materiale og et lerindhold, der ligger mellem mindst 1,8 og ca. 37%. De pâgældende data pâ sojabonner i dyndet 1er af Wabash-typen var ubestemmelig i dette forsog. De angivne selektivitetsfaktorer i 1er af Sarpy-typen og dyn-10 det 1er af Drummer-typen og Florida-dyregodning er minimale værdier, fordi den maksimale pâferingsintensitet under forsoget var 2,24 kg/ha, og herbicidet var sikkert i sojabonner ved den samme pâforingsintensitet over 2,24 kg/ha.The data set forth in Table XV shows that the compound of Example 1 is found to be quite insensitive to soil types with varying organic matter content, exhibiting selective control of mercury in soybeans in soils ranging between 1, 0 to 60% organic matter and a clay content between at least 1.8 and approx. 37%. The data on soybeans in the Wabash-type duvets were indeterminate in this experiment. The selected selectivity factors in Sarpy type and Dyn drummer type 1 and Florida animal fertilizers are minimal values because the maximum application intensity during the experiment was 2.24 kg / ha and the herbicide was safe in soybeans at the same application intensity above 2.24 kg / ha.

15 Man gennemforte laboratorieforsog for at bestemme resi-stensen af herbicider ifolge opfindelsen overfor udlud-ning i jorden og resulterende herbicid effektivitet. I disse forsog var forbindelserne fra eksempel 1 og 4 - 5 formuleret i acetone og derpâ i forskellige koncentratio-20 ner sprojtet pâ en afvejet mængde af lerdynd af Ray-ty-pen, der foreligger i urtepotter, som har drænhuller, der er dæ-kket med filtrerpapir, i bunden af urtepotterne.Laboratory experiments were conducted to determine the resistance of herbicides in accordance with the invention to soil leaching and resulting herbicide efficacy. In these experiments, the compounds of Examples 1 and 4 - 5 were formulated in acetone and then sprayed at various concentrations on a weighed amount of Ray-type clay dung present in herbal pots which have drainage holes covered. lined with filter paper, at the bottom of the herbal pots.

De urtepotter, der indeholder den behandlede jord, blev udsat for udludning, ved at placere dem pâ et drejebord, 25 der roterede under to dysespidser fra en vandbeholder, der var kalïb'reret til at levere 2,54 cm vand pr. time, hvilket simulerede regnfald. Udludningshastigheder blev indstillet ved at variere tidsrummet pâ drejebordet. Man leverede vand til jorden i urtepotterne og lod det per-30 colere gennem filtrerpapiret og drænhullerne. Man lod derpâ urtepotterne henstâ i tre dage ved omgivelsernes tem-peratur. Den behandlede jord i urtepotterne blev derpâ fjernet, smuldret og indfort som et overfladelag pâ top-pen af andre urtepotter, der indeholder de ovenfor an-35 givne jordtyper, hvori der er sâet fro af hanespore. Ur-The herb pots containing the treated soil were subjected to leaching by placing them on a turntable, rotating under two nozzle tips from a water container calibrated to deliver 2.54 cm of water per day. hour, which simulated rainfall. Leaching rates were set by varying the time on the turntable. Water was supplied to the soil in the herbal pots and allowed to percolate through the filter paper and drainage holes. The herb pots were then left to stand for three days at ambient temperature. The treated soil in the herb pots was then removed, crumbled and inserted as a surface layer on top of other herb pots containing the above-mentioned soil types in which seeds of male spores were sown. Clock-

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40 tepotterne blev derpâ indfort i drivhusbænke, vandet kun-stigt nedefra og hensat til vækst i 2 - 3 uger. Man re-gistrerede visuelle karaktergivninger hvad angâr procen-tisk vækstinhibering i sammenligning med som blindpreve 5 tjenende (behandlede) urtepotter og friske vægte for hanespore; de data, der hidrorer fra kontrolpr0ven, re-præsenterer 6 gentagne forsog, og de data, der hidrorer fra forsogsforbindelserne, repræsenterer 3 gentagne for-sagt forsogsdata er vist i tabel XVI. Friske vægte af 10 ukrudtet blev ikke malt for forsegene i magert lerdynd af Drummer-typen.The 40 teapots were then placed in greenhouse benches, watered down from below and allowed to grow for 2-3 weeks. Visual gradings were recorded in terms of percent growth inhibition as compared to blind spot 5 serving (treated) herbal pots and fresh weights for male spores; the data derived from the control sample represent 6 repeated attempts and the data derived from the test compounds represent 3 repeated predicted test data are shown in Table XVI. Fresh weeds of the 10 weeds were not painted for the drummers in lean drummer-type earthenware.

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4444

En henvisning til de i tabel XVI angivne data viser, at forbindelserne ifolge opfindelsen var ret resistente overfor udludning i jorden under varierende betingelser, hvad angâr regnfald. Det kan især anfores, at enhver af 5 forbindelserne ifolge opfindelsen ved pâforingsintensite-ten 2,24 kg/ha kontrollerede hanespore under et regnfald, der var ækvivalent med 10,16 cm i lerdynd af Ray-typen og magert lerdynd af Drummer-typen, med undtagelse af forbindelserne fra eksempel 1 og 5 i dynd af Ray-typen, 10 hvor man bibeholdt kontrol under et regnfald, der var ækvivalent med 5,03 cm. Selv ved den lave pâforingsinten-sitet pâ 0,14 kg/ha kontrollerede forbindelserne fra eksempel 1, 4 og 5 hanespore i magert lerdynd af Drummer-typen under et regnfald, der var ækvivalent med 5,08 cm.A reference to the data set out in Table XVI shows that the compounds of the invention were quite resistant to leaching in the soil under varying rainfall conditions. In particular, it can be stated that any of the 5 compounds of the invention at the application intensity controlled 2.24 kg / ha of controlled male spores during a rainfall equivalent to 10.16 cm in Ray-type clay and Drummer-type lean clay, with the exception of the compounds of Examples 1 and 5 in Ray-type duvets, 10 where control was maintained during a rainfall equivalent to 5.03 cm. Even at the low application intensity of 0.14 kg / ha, the compounds of Examples 1, 4, and 5 controlled the male drummer groove in the drummer-type thin clay during a rainfall equivalent to 5.08 cm.

15 Toxicologiske studier af forbindeïsen fra eksempel 1 har vist, at forbindeïsen er helt sikker. Den er en lille smule toxisk (OLD^g 2300 mg/kg; MLD^g >5010 mg/kg) og udviser en ringe <zjeirritation og ingen hudirritation.Toxicological studies of the compound from Example 1 have shown that the compound is completely safe. It is slightly toxic (OLD ^ g 2300 mg / kg; MLD ^ g> 5010 mg / kg) and exhibits slight irritation and no skin irritation.

Ingen specielle hândteringsmetoder udover normale for-\ 20 holdsregler er anset for nodvendige.No special handling methods other than normal precautions are considered necessary.

Det vil derfor pâ basis af den i det foregâende angivne, detaljerede beskrivelse forstâs, at forbindelser ifolge opfindelsen har vist uventede og fremragende overlegne herbicide egenskaber, bâde absolut og i forhold til de 25 mest relevante kendte forbindelser, hvad angâr struktur.It will therefore be understood from the foregoing detailed description that compounds of the invention have exhibited unexpected and outstandingly superior herbicidal properties, both absolutely and in relation to the 25 most relevant known compounds in terms of structure.

Især har det vist sig, at forbindelserne ifolge opfindelsen er fremragende selektive herbicider, især hvad angâr kontrol af vanskeligt udryddelige, flerârige og etârige græsser i -sojabonner og majs, men ogsâ i jordnodder, bom-30 uld og andre afgroder. Det kan yderligere anfores, at forbindelser ifolge opfindelsen udviser fremragende kontrol af flerârige ukrudt, sâsom kvikgræs og forskellige typer af "nutsedge" og resistente etârige græsser, sâsom Texas panicum, klogræs, vild proso-hirse, alexandergræs,In particular, it has been found that the compounds of the invention are excellent selective herbicides, especially as regards the control of difficult extinct, perennial and annual grasses in soybeans and maize, but also in groundnuts, cotton and other crops. It can be further stated that compounds of the invention exhibit excellent control of perennial weeds, such as mercury and various types of "nutsedge" and resistant annual grasses, such as Texas panicum, clover grass, wild prose millet, alexander grass,

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45 durra-kimplante, "shattercane" og/eller rod ris, mens de ogsâ kontrollerer og/eller undertrykker andre, mindre re-sistente etârige græsser og flerârige planter.45 sorghum seedling, "shattercane" and / or root rice, while also controlling and / or suppressing other, less resistant annual grasses and perennials.

De herbicide blandinger if0lge opfindelsen, herunder kon-5 centrater, der kræver fortynding fer pâforing, indeholder mindst en aktiv bestanddel og et adjuvans i flydende el-ler fast form. Blandingerne fremstilles ved at blande den aktive bestanddel med et adjuvans, herunder fortyndings-midler, strækkenfidler, bærere og konditioneringsmidler, 10 til tilvejebringelse af blandinger i form af findelte, partikelformede, faste stoffer, granulater, tabletter, oplosninger, dispersioner eller emulsioner. Den aktive bestanddel kan sâledes anvendes med et adjuvans, sâsom et findelt, fast stof, en væske af organisk oprindelse, 15 vand, et befugtningsmiddel, et dispergeringsmiddel, et emulgeringsmiddel eller enhver passende kombination deraf.The herbicidal compositions of the invention, including concentrates which require dilution to be applied, contain at least one active ingredient and adjuvant in liquid or solid form. The mixtures are prepared by mixing the active ingredient with an adjuvant, including diluents, stretching agents, carriers and conditioning agents, to provide mixtures in the form of finely divided, particulate, solids, granules, tablets, solutions, dispersions or emulsions. The active ingredient can thus be used with an adjuvant such as a finely divided solid, a liquid of organic origin, water, a wetting agent, a dispersant, an emulsifier or any suitable combination thereof.

Blandingerne ifelge opfindelsen, især væsker og befugte-lige pulvere, indeholder fortrinsvis som konditionerings-middel et eller fbere overfladeaktive midler i mængder, 20 der er tilstrækkelige til at gore en given blanding let dispergerbar i vand eller i olie. Inkorporeringen af et overfladeaktivt middel i blandingen forbedrer i hoj grad dens effektivitetΓ Ved betegnelsen "overfladeaktivt middel" forstâs blandt andre befugtningsmidler, disperge-25 ringsmidler, suspenderingsmidler og emulgeringsmidler.The compositions of the invention, especially liquids and wettable powders, preferably contain as a conditioning agent one or more surfactants in amounts sufficient to make a given mixture readily dispersible in water or in oil. The incorporation of a surfactant into the mixture greatly improves its effectiveness. The term "surfactant" is understood to include, inter alia, wetting agents, dispersing agents, suspending agents, and emulsifying agents.

Anioniske, kationiske og ikke-ioniske midler kan anvendes med lige stor lethed.Anionic, cationic and nonionic agents can be used with equal ease.

Foretrukne befugtningsmidler er alkylbenzen- og alkyl-naphthalensulfonater, sulfaterede fedtalkoholer, aminer 30 eller sure amider, langkædede, sure estere af natrium- isothionat, estere af natrium-sulfosuccinat, sulfaterede eller sulfonerede fedtsyreestere, jordoliesulfonater, sulfonerede vegetabilske olier, di-tertiæte acetylenskePreferred wetting agents are alkylbenzene and alkyl naphthalene sulfonates, sulfated fatty alcohols, amines 30 or acidic amides, long chain acidic esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters, petroleum sulfonated, sulfonated, sulfonated, sulfonated

DK 157189 BDK 157189 B

46 glycoler, polyoxyethylenderivater af alkylphenoler (især isooctylphenol og nonylphenol) og polyoxyethylenderivater af de hojere mono-fedtsyreestere af hexitolanhydrider, f. eks. sorbitan. Foretrukne dispergeringsmidler er methyl-5 cellulose, polyvinylalkohol, natriumligninsulfonater, po lymère alkyl-naphthalen-sulfon&ter, natrium-naphthalen-sulfonater og polymethylenbisnaphthalen-sulfonaterne.46 glycols, polyoxyethylene derivatives of alkyl phenols (especially isooctylphenol and nonylphenol) and polyoxyethylene derivatives of the higher mono fatty acid esters of hexitol anhydrides, eg sorbitan. Preferred dispersants are the methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl-naphthalene sulfonates, sodium naphthalene sulfonates, and polymethylene bisnaphthalene sulfonates.

Befugtelige pulvere er med vand dispergerbare blandinger, der indeholder en eller flere aktive bestanddele, et in-10 different, fast strækkemiddel og et eller flere befugt-nings- eller dispergeringsmidler. De indifferente, faste strækkemidler er sædvanligvis af mineralsk oprindelse, sasom de naturlige lerarter, diatoméjorder og syntetiske mineraler, der er afledt af silica eller lignende. Eks-15 empler pâ sâdanne strækkemidler omfatter kaolinitler, attapulgitler og syntetisk magnesiumsilicat. De befugtelige pulverblandinger ifolge opfindelsen indeholder sædvanligvis mellem ca. 0,5 og 60 dele (fortrinsvis 5-20 dele) aktiv bestanddel, fra ca. 0,25 til 25 dele (for-20 trinsvis 1-15 dele) befugtningsmiddel, fra ca. 0,25 dele til 25 dele (fortrinsvis 1,0 - il5 dele) disperge-ringsmiddel og fra 5 til ca. 95 dele (fortrinsvis 5-50 dele) indifferent, fast strækkemiddel, hvorved aile dele er pâ vægtbasis i forhold til den totale blanding. Om 25 nodvendigt kan fra ca. 0,1 til 2,0 dele af det faste strækkemiddel erstattes af en korrosionsinhibitor eller antiskummemiddel eller begge.Wettable powders are water-dispersible mixtures containing one or more active ingredients, an in-different, solid extender, and one or more wetting or dispersing agents. The inert solid surfactants are usually of mineral origin, such as the natural clays, diatomaceous earths and synthetic minerals derived from silica or the like. Examples of such extenders include kaolin nitrates, attapulgitels and synthetic magnesium silicate. The wettable powder mixtures according to the invention usually contain between approx. 0.5 and 60 parts (preferably 5-20 parts) of active ingredient, from approx. 0.25 to 25 parts (preferably 1 to 15 parts) wetting agent, from approx. 0.25 parts to 25 parts (preferably 1.0 - 15 parts) of dispersant and from 5 to approx. 95 parts (preferably 5-50 parts) of inert, solid extender, all parts being by weight relative to the total mixture. About 25 can be needed from approx. 0.1 to 2.0 parts of the solid extender is replaced by a corrosion inhibitor or anti-foaming agent or both.

André formuleringer omfatter pudderkoncentrater omfatten-de fra 0,1 til 60 vægt-% af den aktive bestanddel pâ et 30 passende strækkemiddel; disse puddere kan være fortyndet med henblik pâ pâforing i koncentrationer, der ligger in-denfor intervallet fra ca. 0,1 til 10 vægt-%.Other formulations comprise powder concentrates comprising from 0.1 to 60% by weight of the active ingredient on a suitable excipient; these powders may be diluted for application at concentrations within the range of about 0.1 to 10% by weight.

Vandige suspensioner eller emulsioner kan fremstilles vedAqueous suspensions or emulsions may be prepared by

DK 157189 BDK 157189 B

47 at omrore en vandig blanding af en vanduoploselig, aktiv bestanddel og et emulgeringsmiddel indtil ensartethed og ved derpâ at homogenisere til dannelse af en stabil émulsion med meget findelte partikler. Den resulterende, kon-5 centrerede vandige suspension er karakteriseret ved sin yderst ringe partikelstorrelse, sâledes at dækningen er meget ensartet, nâr fortynding og sprojtning er gennem-fert. Passende koncentrationer af disse formuleringer in-deholder mellem ca, 0,1 og 60%, fortrinsvis 5 - 50% pâ 10 vægtbasis af aktiv bestanddel, hvorved den ovre grænse er bestemt ved oploselighedsgrænsen af aktiv bestanddel i oplesningsmidlet.47 to stir an aqueous mixture of a water-insoluble active ingredient and an emulsifier to uniformity, and then homogenize to form a stable emulsion with very finely divided particles. The resulting concentrated aqueous suspension is characterized by its extremely small particle size, so that the coverage is very uniform when dilution and spraying are complete. Appropriate concentrations of these formulations contain between about 0.1% and 60%, preferably 5 - 50% on a 10 weight basis of active ingredient, whereby the upper limit is determined by the solubility limit of active ingredient in the solvent.

I en anden form for vandige suspensioner indkapsler man et med vand ublandbart herbicid til dannelse af en mikro-15 inkapsuleret fase dispergeret i en vandig fase. Ved en udforelsesform dannes der smâ kapsler ved sammenbringning af en vandig fase indeholdende et som emulgeringsmiddel tjenende ligninsulfonat og et med vand ublandbart kemika-lium og polymethylenrpolyphenylisocyanat, idet man dis-20 pergerer den med vand ublandbare fase i den vandige fase efterfulgt af tilsætning af en polyfunktionel amin. Iso-cyanat- og aminforbindelserne reagerer til dannelse af en fast vægskal ’eff urinstof rundt omkring partikler af det med vand ublandbare kemikalium, idet der pâ denne 25 mâde dannes mikrokapsler deraf. Generelt vil koncentra-tionen af mikroindkapslet materiale ligge mellem ca. 480 og 700 g/1 af din totale blanding, fortrinsvis mellem 480 og 600 g/1.In another form of aqueous suspensions, a water-immiscible herbicide is encapsulated to form a microencapsulated phase dispersed in an aqueous phase. In one embodiment, small capsules are formed by joining an aqueous phase containing an emulsifier serving as lignin sulfonate and a water-immiscible chemical and polymethylene polyphenyl isocyanate, dispersing it with water-immiscible phase in the aqueous phase followed by the addition of an aqueous phase. polyfunctional amine. The isocyanate and amine compounds react to form a solid wall-shell urea around particles of the water-immiscible chemical, thereby forming microcapsules thereof. In general, the concentration of microencapsulated material will be between ca. 480 to 700 g / l of your total mixture, preferably between 480 and 600 g / l.

Koncentrater er sædvanligvis oplosninger af aktive bestand-30 dele i med vand ublandbare eller delvis med vand ublandbare oplosningsmidler sammen med et overfladeaktivt mid-del. Passende oplosningsmidler til den aktive bestanddel ifolge opfindelsen omfatter dimethylformamid,. dimethyl-sulfoxid, N-methylpyrrolidon, carbonhydrider og med vandConcentrates are usually solutions of active ingredients in water-immiscible or partially water-immiscible solvents together with a surfactant. Suitable solvents for the active ingredient of the invention include dimethylformamide. dimethylsulfoxide, N-methylpyrrolidone, hydrocarbons and with water

DK 157189 BDK 157189 B

48 ublandbare ethere, estere eller ketoner. Man kan imidler -tid formulere andre flydende koncentrater af hoj styrke ved at oplose den aktive bestanddel i et opl0sningsmiddel og ved derpâ at fortynde, f.eks. med pêtroleum, til sproj-5 tekoncentration. De her omhandlede koncentratblandinger indeholder generelt fra ca. Qrl til 95 dele (fortrinsvis 5-60 dele) aktiv bestanddel, ca. 0,25 til 50 dele (fortrinsvis 1-25 dele) overfladeaktivt middel, og om nod-vendigt ca. 4 til 94 dele oplosningsmiddel, hvorved aile 10 dele er pâ vægtbasis, beregnet i forhold til den totale vægt af emulgerbar olie.48 immiscible ethers, esters or ketones. However, other high strength liquid concentrates can be formulated by dissolving the active ingredient in a solvent and by diluting thereto, e.g. with petroleum, for spray-5 tea concentration. The concentrate compositions herein generally contain from ca. Qrl to 95 parts (preferably 5-60 parts) of active ingredient, approx. 0.25 to 50 parts (preferably 1-25 parts) of surfactant, and if necessary approx. 4 to 94 parts of solvent, whereby all 10 parts are by weight, calculated in relation to the total weight of emulsifiable oil.

Granulater er i fysisk henseende stabile, partikelformede blandinger omfattende aktiv bestanddel, der adhærerer til eller som er fordelt over en basismatrix af et indiffe-15 rent, findelt, partikelformet strækkemiddel. For at un-derstotte udludningen af den aktive bestanddel fra det partikelformede materiale kan et overfladeaktivt middel, sâsom et af dem, der er opfort i det foregâende, være til stede i blandingen. Naturlige lerarter, sâsom pyrophyl-20 litler, illit og vermiculit, er eksempler pâ funktions- dygtige klasser af partikelformede, mineraiske strække-midler. De foretrukne strækkemidler er de porose, absor-berende, forud tildannede partikler, sâsom forud tildan-net og sigtet, partikelformet attapulgit eller varmeeks-25 panderet, partikelformet vermiculit og de findelte lerarter, sâsom kaolinler, hydratiseret attapulgit eller bentonitiske lerarter. Disse strækkemidler sprojtes eller blandes med den aktive bestanddel til dannelse af de herbicide granulater.Granules are physically stable, particulate mixtures comprising active ingredient adhering to or distributed over a base matrix of an indifferent, finely divided particulate extender. In order to support the leaching of the active ingredient from the particulate material, a surfactant such as one of those listed above may be present in the mixture. Natural clays, such as pyrophyllites, illite and vermiculite, are examples of functional classes of particulate, mineral extracts. The preferred extenders are the porous, absorbent, preformed particles, such as preformed and sieved, particulate attapulgite or heat-expanded, particulate vermiculite, and the finely divided clays, such as kaolin clays, hydrated attapulgite or bentonite clays. These extenders are sprayed or mixed with the active ingredient to form the herbicidal granules.

30 Granulatblandingen ifolge opfindelsen kan indeholde mel-lem ca. 3 og 20 dele pâ vægtbasis af aktiv bestanddel pr.The granulate composition according to the invention may contain between ca. 3 and 20 parts by weight of active ingredient per

100 vægtdele 1er og 0 til ca. 5 vægtdele overfladeaktivt middel pr. 100 vægtdele partikelformet 1er.100 parts by weight 1 and 0 to approx. 5 parts by weight of surfactant per 100 parts by weight of particulate 1er.

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4949

Blanddingerne if0lge opfindelsen kan ogsâ indeholde andre additiver, f.eks. godningsmidler, andre herbicider, andre pesticider, sikringsmidler og lignende, der anvendes soin adjuvanser eller i kombination med ethvert af de ovenfor 5 beskrevne adjuvanser. Kemikalier, der er anvendelige i kombination med de aktive bestanddele ifolge opfindelsen, omfatter f.eks. triaziner, urinstoffer, carbamater, acet-amider, acetanilider, uraciler, eddikesyre eller phenol-derivater, thiolcarbamater, triazol, benzoesyrer, nitri-10 1er, biphenylethere og lignende, sâsom:The mixtures of the invention may also contain other additives, e.g. fertilizers, other herbicides, other pesticides, safeners and the like used in soin adjuvants or in combination with any of the adjuvants described above. Chemicals useful in combination with the active ingredients of the invention include e.g. triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic or phenol derivatives, thiol carbamates, triazole, benzoic acids, nitrates, biphenyl ethers and the like, such as:

Heterocvcliske nitrogensvovlderivater 2- chl or-4- ethylamino - 6 - i s opr opylamino - s - tr iaz in 2-chlor-4,6-bis ( i s opr opylamino ) -s-triazin 2- chlor-4,6-bis(ethylamino)-s-triazin 15 3-is opropyl-1H-2,1,3-benz oethiadiazin-4-( 3H ) -on-2,2-dioxid 3- amino-l,2,4-triazol 6,7-dihydrodipyrido(l,2-a:2f,1'-c)-pyrazidiniumsalt 5-brom-3-isopropyl-6-methyluracil 1,1*-dimethyl-4,41-bipyridinium 20 Urinstoffer N'-( 4-chlorpb.eno2cy ) -phenyl-N, N-dimethylurinstof N, N-dimethyl-N ’ - ( 3-chlor-4-methylphenyl)urinstof 3-(3,4-dichlorphenyl)-1,1-dimethylurinstof 1,3-dimethyl-3-(2-benzothiazolyl)-urinstof 25 3-(p-chlorphenyl)-l,1-dimetbylurinstof l-butyl-3- (3 > 4-diclilorphenyl) -1-methylurinstofHeterocyclic nitrogen sulfur derivatives 2-chloro-4-ethylamino-6-is on opylamino-s-triaz in 2-chloro-4,6-bis (is on opylamino) -s-triazine-2-chloro-4,6-bis ( ethylamino) -s-triazine 3-isopropyl-1H-2,1,3-benzoethiadiazine-4- (3H) -one-2,2-dioxide 3-amino-1,2,4-triazole 6.7 -dihydrodipyrido (1,2-a: 2f, 1'-c) -pyrazidinium salt 5-bromo-3-isopropyl-6-methyluracil 1,1 * -dimethyl-4,41-bipyridinium Urea N '- (4-chloropbb phenyl-N, N-dimethylurea N, N-dimethyl-N '- (3-chloro-4-methylphenyl) urea 3- (3,4-dichlorophenyl) -1,1-dimethylurea 1,3-dimethyl -3- (2-benzothiazolyl) urea 3- (p-chlorophenyl) -1,1-dimethylurea 1-butyl-3- (3> 4-dichlorophenyl) -1-methylurea

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5050

Carbamater/thiolcarbamater 2-chlorallyl-diethyldithiocarbamat S--(4-chlorbenzyl)-N,N-diethylthiolcarmabat isopropyl-N-(3-chlorphenyl)-carbamat 5 S-2,3-dichlorallyl-N,N-diisopropylthiolcarbamat ethyl-N, N-dipropylthiolcarbamat S-propyl-dipropylthiolcarbamatCarbamates / thiol carbamates 2-chloroallyl diethyldithiocarbamate S - (4-chlorobenzyl) -N, N-diethylthiolcarbabate isopropyl-N- (3-chlorophenyl) carbamate S-2,3-dichloroallyl-N, N-diisopropylthiolcarbamate , N-dipropylthiol carbamate S-propyl dipropylthiol carbamate

Acetamider/acetanilider/aniliner/amider 2-chlor-N,N-diallylacetamid 10 N,N-dimethyl-2,2-diphenylacetamid N-(2,4-dimethyl-5-[[(trifluormethylsulfonyl]amino]phenyl)-acetamid N-isopropyl-2-chloracetanilid ~ 2’,6’-diethyl-N-methoxymëthyl-2-chloracetanilid 15 21-methyl-6’-ethyl-N-(2-methoxyprop-2-yl)-2-chloracet- anilid a,a,a-trifluor-2,6-dinitro-N,N-dipropyl-p-toluidin N-(1,1-dimethylpropynyl)-3,5-dichlorbenzamidAcetamides / acetanilides / anilines / amides 2-chloro-N, N-diallylacetamide N, N-dimethyl-2,2-diphenylacetamide N- (2,4-dimethyl-5 - [[(trifluoromethylsulfonyl] amino] phenyl) -acetamide N-isopropyl-2-chloroacetanilide ~ 2 ', 6'-diethyl-N-methoxymethyl-2-chloroacetanilide 21-methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide α, α, α-Trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide

Syrer/estere/alkoholer 20 2,2-dichlorpropionsyre 2- methyl-4-chlorphenoxyeddikesyre 2,4-dichlorphenoxyeddikesyre methyl-2-[4-(2,4-dichlorphenoxy)phenoxy]propionat 3- amino-2,5-dichlorbenzoesyre 25 2-methoxy-3,6-dichlorbenz oesyre 2,3,6-tr ichlorphenyleddikesyre N-l-naphthylphthalamidsyre natrium-5- [ 2- chlor-4- ( tr if luormethyl ) phenoxy ] - 2-nitr oben-zoat 30 4,6-dinitro-o-sek.-butylphenol N-(phosphonomethyl)-glycin og dens ^-6 monoa 1 ky 1 amin - og alkalimetalsalte og kombinationer deraf.Acids / esters / alcohols 2,2-dichloropropionic acid 2-methyl-4-chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propionate 3-amino-2,5-dichlorobenzoic acid 2-methoxy-3,6-dichlorobenzoic acid 2,3,6-trichlorophenylacetic acid N1-naphthylphthalamic acid sodium 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate 4.6 -dinitro-o-sec-butylphenol N- (phosphonomethyl) -glycine and its β -6 mono 1 ky 1 amine and alkali metal salts and combinations thereof.

5151

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Ethere 2,4-dichlorphenyl-4-nitrophenyl-ether 2-chlor-oc, a, a-trif luor-p-t olyl-3-ethoxy-4-nitrodiph.enyl-ether 5 Diverse 2,6-dicMorbenzonnitrilEthere 2,4-dichlorophenyl-4-nitrophenyl ether 2-chloro-α, α, α-trifluoro-p-tolyl-3-ethoxy-4-nitrodiphenyl ether 5 Miscellaneous 2,6-dichlorobenzonitrile

Mononatriumsyre, methanarsonat dinatrium-methanars onat . « esMonosodium Acid, Methanarsonate Disodium Methanars onat. «Es

Godningsmidler, der kan anvendes i kombination med de 10 aktive bestanddele, omfatter f.eks. aramoniumnitrat urin- stof, potaske og superphospbat. André nyttige additiver omfatter materialer, i bvilke planteorganismer kan slâ rod og vokse, sâsom kompost, dyregodning, humus, sand og lignende.Fertilizers which can be used in combination with the 10 active ingredients include e.g. aramonium nitrate urea, potash and superphosphate. Other useful additives include materials in which plant organisms can root and grow, such as compost, animal manure, humus, sand and the like.

15 Herbicide formulêriïiger af de ovenfor beskrevne typer er eksemplificeret i adskellige illustrerende udforelsesfor-mer, der er angivet i det folgende.Herbicidal formulations of the types described above are exemplified in various illustrative embodiments set forth below.

I. Emulgerbare koncentrater Vægtprocent A. Forbindelse fra eksempel nr. 1 50,0 2 0 Calciumdodecylbenzensulfonat/ polyoxyethylenethere blanding (f. eks. Atlox® 3437F) 4,35I. Emulsifiable Concentrates Weight Percent A. Compound of Example No. 50.0 2 0 Calcium dodecylbenzenesulfonate / polyoxyethylene ether mixture (e.g. Atlox® 3437F) 4.35

Calciumdodecylbenzensulfonat ("FloMo") 0,15 25 Cg aromatisk oplosningsmiddel 45,00 100,00 52Calcium dodecylbenzenesulfonate ("FloMo") 0.15 25g aromatic solvent 45.00 100.00 52

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B. Forbindelse fra eksempel nr. 4 85,0B. Compound of Example No. 4 85.0

Calciumdode cylsulf onat/alkyl- arylpolyetheralkohol blanding 4,0Calcium kill cylsulfonate / alkyl aryl polyether alcohol mixture 4.0

Cg armatiske carbonhydrider 11,0 5 opl0sningsmiddel 100,00 C. Forbindelse fra eksempel nr. 6 5,0Cg Armatic Hydrocarbons 11.0 5 Solvent 100.00 C. Compound of Example No. 6 5.0

Cale iumdode cylbenz en-sulf onat/ polyoxyethylenethere blanding— - (f. eks. Atlox® 3437) 1,0 10 Xylen 94,0 100,00 II. Flydende koncentrater - -------- Vaegtprocent A. Forbindelse fra eksempel nr. 4 10,0Calcium dodecyl benzene sulfonate / polyoxyethylene ether mixture - - (e.g. Atlox® 3437) 1.0 10 Xylene 94.0 100.00 II. Liquid Concentrates - -------- Weight Percent A. Compound of Example No. 4 10.0

Xylen 90,0 100,00 15 B. Forbindelse fra eksempel nr. 5 85,0Xylene 90.0 100.00 15 B. Compound of Example No. 5 85.0

Dimethylsulfoxid 15,0 100,00 C. Forbindelse fra eksempel nr. 6 50,0 N-methylpyrrolidon 50,0 100,00Dimethyl Sulfoxide 15.0 100.00 C. Compound of Example No. 6 50.0 N-methylpyrrolidone 50.0 100.00

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53 D. Forbindelse fr eksempel nr. 7 5,0 ethoxyleret ricinusolie 20,0 "Rhodamin B" 0,553 D. Compound Example 7 5.0 Ethoxylated Castor Oil 20.0 "Rhodamine B" 0.5

Dinethylformamid 74,5 100,00 5 III. Emulsioner A. Forbindelse fra eksempel nr. 12 40,0 polyoxyethylen/polyoxypropylenblok med butanol (f. eks. Tergitol^'XH) 4,0Dinethylformamide 74.5 100.00 5 III. Emulsions A. Compound of Example 12 40.0 polyoxyethylene / polyoxypropylene block with butanol (e.g. Tergitol® XH) 4.0

Vand _ 56,0 100,00 10 B. Forbindelse fra eksempel nr. 13 5,0Water - 56.0 100.00 10 B. Compound of Example 13 5.0

Polyoxyethylen/polyoxypropylenblok- copolymer med butanol ..... - -...... 3,5Polyoxyethylene / polyoxypropylene block copolymer with butanol ..... - -...... 3.5

Vand - 91,5 100,00 IV. Befugtelige pulvere Vægtprocent 15 A. Forbindelse fra eksempel nr. 1 25,0 natriumlignosulfonat 3,0 natrium-N-methyl-N-oleyl-taurat 1,0Water - 91.5 100.00 IV. Wettable Powders Weight Percentage 15 A. Compound of Example No. 25.0 Sodium Ligosulfonate 3.0 Sodium N-Methyl-N-Oleyl Taurate 1.0

Amorft silica (syntetisk) 71,0 100,00 B. Forbindelse fra eksempel nr. 12 80,0 20 natriumdioctylsulfosuccinat 1,25 calciumligno'sulfonat 2,75Amorphous Silica (Synthetic) 71.0 100.00 B. Compound of Example No. 12 80.0 20 Sodium Dioctyl Sulfosuccinate 1.25 Calcium Ligosulfonate 2.75

Amorft silica (syntetisk) 16,00 54Amorphous silica (synthetic) 16.00 54

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C. Forbindelse fra eksempel nr. 13 10,0 natriumlignosulfonat 3?0 5 natr ium-jW-methyl-N- oleyl-taurat 1}0C. Compound of Example No. 13 10.0 Sodium Ligosulfonate 3? 0 5 Sodium N-methyl-N-oleyl taurate 1} 0

Kaolinitler 86,0 100,00 V. Puddere Vægf/procent A. Forbindelse fra eksempel nr. 7 2,0Kaolinitels 86.0 100.00 V. Powders Wall / percent A. Compound of Example No. 7 2.0

Attapulgit 98.QAttapulgit 98.Q

100,00 10 B. Forbindelse fra eksempel nr. 8 60,0100.00 Compound of Example No. 8 60.0

Montmorillonit 4-0*0 100,0 C. Forbindelse fra eksempel nr. 9 30,00Montmorillonite 4-0 * 0 100.0 C. Compound of Example No. 9 30.00

Bentonit _72?, 2- 100,00 D. Forbindelse fra eksempel nr. 10 1,0 15 Diatoméjord ____99j_0 100,00 VI. Granulater Vægtnrocent A. Forbindelse fra eksempel nr. 1 15,0Bentonite _72?, 2- 100.00 D. Compound of Example No. 10 1.0 15 Diatomaceous earth ____99j_0 100.00 VI. Granules Weight Percent A. Compound of Example No. 15.0

Granulært attapulgit (20/40 mesh) 85,0 100,00Granular attapulgite (20/40 mesh) 85.0 100.00

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55 B. Forbindelse fra eksempel nr. 6 30,0B. Compound of Example No. 6 30.0

Diatoméjord (20/40) —7.2:,.QDiatomaceous Earth (20/40) —7.2:, .Q

- 100,00 C. Forbindelse fra eksempel nr. 12 0,5- 100.00 C. Compound of Example No. 12 0.5

Bentonit (20/40) 99^ 100,00 5 D. Forbindelse fra eksempel nr. 13 5,0Bentonite (20/40) 99 ^ 100.00 5 D. Compound of Example No. 13 5.0

Pyrophyllit (20/40) 95^0.....Pyrophyllite (20/40) 95 ^ 0 .....

100,00 VII. Mikrokapsler -.....--..... Vægtprocent A. Forbindelse fra eksempel nr. 1 indkap- slet i skalvæg af polyurinstof · 49,2 10 natriumlignôsulfonat (f. éks. Reax ^88 B) 0,9100.00 VII. Microcapsules -... - .....% by weight A. Compound of Example # 1 enclosed in polyurea shell · 49.2 10 Sodium lignosulfonate (e.g. Reax ^ 88 B) 0.9

Vand 49.9 100,00 B. Forbindelse fra eksempel nr. 12 indkapslet i skalvæg af polyurinstof 10,0Water 49.9 100.00 B. Compound of Example 12 enclosed in polyurea shell wall 10.0

Kaliumlignosulfonat (f.eks. Reax^c-21) 0,5 15 Vand ' 89.5 100,00 C. Forbindelse fra eksempel nr. 13 indkapslet i skalvæg af polyurinstof 80,0Potassium lignosulfonate (eg Reax® c-21) 0.5 15 Water 89.5 100.00 C. Compound of Example # 13 encapsulated in polyurea shell 80.0

Magnesiumsalt af lignosulfat ("Treax, LTN") 2,0Magnesium salt of lignosulfate ("Treax, LTN") 2.0

Vand 18,0 100,00Water 18.0 100.00

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56 Nâr man arbejder i henhold til opfindelsen, pâf0rer man effektive mængder af acetaniliderne ifolge opfindelsen pâ den jord, der indeholder planterne, eller de inkorpore-res i akvatiske medier pâ ehhver passende mâde. Pâforin-5 gen af flydende og partikelformede, faste blandinger pâ jorden kan gennemfores under anvendelse af konventionelle metoder, f. eks. pudringsorganer med energitilforsel, bomsprojtere og manuelle sprojtere og sprojteforstovere. Blandingerne kan ogsâ pâf0res fra fly som et pudder eller 10 en forstovet masse pâ grund af deres effektivitet ved lave doser. Pâforingen af herbicide blandinger til akvatiske planter gennemfores sædvanligvis ved at tilsætte blandingerne til de akvatiske medier pâ det omrâde, hvor man on-sker kontrol af de akvatiske planter.56 When operating in accordance with the invention, effective amounts of the acetanilides of the invention are applied to the soil containing the plants or incorporated into aquatic media in any appropriate manner. The application of liquid and particulate solid mixtures to the soil can be carried out using conventional methods, for example powders with energy supply, boom sprayers and manual sprayers and sprayers. The mixtures may also be applied from aircraft as a powder or a nebulized mass due to their effectiveness at low doses. The application of herbicidal mixtures to aquatic plants is usually accomplished by adding the mixtures to the aquatic media in the area where the aquatic plants are controlled.

15 Pàforingen af en effektiv mængde af fprbindelserne ifelge opfindelsen pâ voksestedet for de uonskede ukrudtsarter er essentiel og kritisk for udovelsen af opfindelsen. Den nojagtige mængde af aktiv bestanddel, som skal anvendes, afhænger af forsekllige faktorer, herunder plantearten og 20 udviklingstrinnet deraf, typen og tilstanden af jorden, mængden af regnfald og det specifikt anvendte acetanilid.The application of an effective amount of the compounds of the invention to the growth site of the undesirable weed species is essential and critical to the practice of the invention. The exact amount of active ingredient to be used depends on various factors, including the plant species and its developmental stage, the type and condition of the soil, the amount of rainfall and the specific acetanilide used.

Ved selektiv pâforing for spiringen pâ planterne eller jordbunden anvender man sædvanligvis en dosering pâ mel-lem 0/02 og ca. 11,2 kg/ha, fortrinsvis fra ca. 0,04 til 25 ca. 5,60 kg/ha eller passende fra 1,12 til 5,6 kg/ha af acetanilid.In selective application for germination on the plants or soil, a dosage is usually applied between 0/02 and approx. 11.2 kg / ha, preferably from approx. 0.04 to 25 approx. 5.60 kg / ha or suitably from 1.12 to 5.6 kg / ha of acetanilide.

Man kan i visse tilfælde kræve lavere eller hojere pâfe-ringsintensiteter. En sagkyndig kan let pâ basis af denne beskrivelse, herunder de ovenfor angivne eksempler, be-30 stemme den optimale pâforingsintensitet, som skal anven-des i ethvert specifikt tilfælde.In some cases lower or higher loading intensities may be required. On the basis of this description, including the examples set forth above, an expert can readily determine the optimum application intensity to be used in any particular case.

Betegnelsen "jord" anvendes i sin bredeste betydning, der skal omfatte aile konventionelle former for "jord”, derThe term "land" is used in its broadest sense to include all conventional forms of "land" which

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57 er defineret i Webster’s New International Dictionary, anden udgave, uafkortet (1961). Dette udtryk refererer sâledes til ethvert materiale eller medium, hvori végétation kan rodfæstes og vokse, og omfatter ikke blot 5 jord, men ogsâ kompost, dyregadning, humus, sand og lig- nende, der er velegnet til at understotte plantevækst.57 is defined in Webster's New International Dictionary, second edition, in full (1961). This term thus refers to any material or medium in which vegetation can be rooted and grow, and includes not only 5 soils, but also compost, animal manure, humus, sand and the like suitable for supporting plant growth.

Claims (36)

1. I 6-stillingen eventuelt med alkyl substituerede N-(0-substitueret-oxymethyl)-2'-trifluormethyl-2-chloracetani-lider, kendetegnet ved, at de har formlen f C1CH0C -CH OR 2 \ / Rl- joj —- 5 hvor R er C-^-alkyl eller alkoxyalkyl eller alkenyl el-ler alkynyl med op til 5 carbonatorner og er hydrogen, methyl eller ethyl; med det forbehold, at R er isopropyl, nâr R^ er hydrogen og R er ethyl, n-pro-10 pyl eller isopropyl, nâr R-^ er ethyl.1. At the 6-position optionally substituted with alkyl, N- (O-substituted-oxymethyl) -2'-trifluoromethyl-2-chloroacetanilides, characterized in that they have the formula f C1CHOC -CH OR2 - wherein R is C 1-6 alkyl or alkoxyalkyl or alkenyl or alkynyl of up to 5 carbon atoms and is hydrogen, methyl or ethyl; with the proviso that R is isopropyl when R 1 is hydrogen and R is ethyl, n-propyl or isopropyl when R 1 is ethyl. 2. Acetanilid ifolge krav 1, kendetegnet ved, at R er C2_^-alkyl.2. Acetanilide according to claim 1, characterized in that R is C2-6 alkyl. 3. Acetanilid ifolge krav 2, kendetegnet ved, at R^ er methyl.Acetanilide according to claim 2, characterized in that R 1 is methyl. 4. Acetanilid if0lge krav 3, kendetegnet ved, at det er N-(ethoxymethyl)-21-trifluormethyl-61-methyl-2-chloracetanilid.Acetanilide according to claim 3, characterized in that it is N- (ethoxymethyl) -21-trifluoromethyl-61-methyl-2-chloroacetanilide. 5. Acetanilid ifolge krav 3, kendetegnet ved, at det er N-(n-propoxymethyl)-2'-trifluormethyl-6,-methyl-20 2-chloracetanilid. 6„ Acetanilid ifolge krav 3» kendetegnet ved, at det er N-(isopropoxymethyl) - 2 '-trifluormethyl-6'-methyl- 2-chloracetanilid. DK 157189 BAcetanilide according to claim 3, characterized in that it is N- (n-propoxymethyl) -2'-trifluoromethyl-6, -methyl-2-chloroacetanilide. 6. Acetanilide according to claim 3 characterized in that it is N- (isopropoxymethyl) -2 '-trifluoromethyl-6'-methyl-2-chloroacetanilide. DK 157189 B 7. Acetanilid ^ iÎ0lge krav 3» kendetegnet ved, at det er N- (isodutoxymethyl )-21 -trifluormethyl- 6'-methyl-2-chloracetanilid.7. Acetanilide according to claim 3, characterized in that it is N- (isodutoxymethyl) -21-trifluoromethyl-6'-methyl-2-chloroacetanilide. 8. Acetanilid if0lge krav 2, kendetegnet ved, 5 at R^ er ethyl.Acetanilide according to claim 2, characterized in that R 1 is ethyl. 9. Acetanilid ifelge krav 3, kendetegnet ved, at det er N-(ethoxymethyl)-2' -trifluormethyl-6 * - ethyl-2-chloracetanilid.Acetanilide according to claim 3, characterized in that it is N- (ethoxymethyl) -2 '-trifluoromethyl-6 * - ethyl-2-chloroacetanilide. 10. Acetanilid ifalge krav 3» kendetegnet ved, 10 at det er N-(n-propoxymethyl)-2'-trifluormethy1-6’-ethyl- 2-chloracetanilid.10. Acetanilide according to claim 3, characterized in that it is N- (n-propoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide. 11. Acetanilid if0lge krav 3, kendetegnet ved, at det er N-(isopropoxymethyl)-2,-trifluormeth.yl-6t-ethyl-2-chloracetanilid.Acetanilide according to claim 3, characterized in that it is N- (isopropoxymethyl) -2, -trifluoromethyl-6t-ethyl-2-chloroacetanilide. 12. Acetanilid i£0lge krav 2, kendetegnet ved, at R1 er hydrogen.12. Acetanilide according to claim 2, characterized in that R1 is hydrogen. 13. Acetanilid if0lge krav 12, kendetegnet ved, at det er N-(isOpropoxymethyl)— 2,-trifluor*niethyl-2-chlor-acetanilid.Acetanilide according to claim 12, characterized in that it is N- (isopropoxymethyl) -2,2-trifluoro-methyl-2-chloro-acetanilide. 14. Acetanilid if0lge krav 1, kendetegnet ved, at R er et C^^-alkenyl-radikal.Acetanilide according to claim 1, characterized in that R is a C C ^^ alkenyl radical. 15. Acetanilid if0lge krav 14, kendetegnet ved, at det er N-(allyloxymethyl)-2,-trifluormet]ayl-6,-methyl-2-chloracetanilid.Acetanilide according to claim 14, characterized in that it is N- (allyloxymethyl) -2, trifluoromethyl] 6-methyl-2-chloroacetanilide. 16. Acetanilid ifelge krav 1, kendetegnet ved, at R er et C^_^-alkynyl-radikal. 1 Acetanilid if0lge krav 16, kendetegnet ved, DK 157189 B at det er N- (propargyloxymethyl )-2 ’ -trif luormethyl-6 * -methyl-2-chloracetanilid.Acetanilide according to claim 1, characterized in that R is a C 1-6 alkynyl radical. 1 Acetanilide according to claim 16, characterized in that it is N- (propargyloxymethyl) -2 '-trifluoromethyl-6 * -methyl-2-chloroacetanilide. 18. Acetanilid lf0lge krav 1, kendetegnet ved, at R er et alkoxyalkyl-radikal med op til 5 carbonatomer.Acetanilide according to claim 1, characterized in that R is an alkoxyalkyl radical having up to 5 carbon atoms. 19. Acetanilid ifalge krav 18, kendetegnet ved, at det er N- (2-methoxyethoxymethyl )-21 -trifluormethyl-6’-methyl-2-chloracetanilid.Acetanilide according to claim 18, characterized in that it is N- (2-methoxyethoxymethyl) -21-trifluoromethyl-6'-methyl-2-chloroacetanilide. 20. Herbicidblanding, kendetegnet ved, at den omfatter et adjuvans og en i herbicid henseende effektiv 10 masngde af et acetanilid ifelge krav 1.20. Herbicide composition, characterized in that it comprises an adjuvant and a herbicide effective amount of an acetanilide according to claim 1. 21. Blanding . ifalge krav 20, kendetegnet ved, at R i acetanilidet er C2_^-alkyl·.21. Mixture. according to claim 20, characterized in that R in the acetanilide is C2-6 alkyl ·. 22. Blanding if0lge krav 21 ^.k endetegnet ved, at R-j_ i acetanilidet er methyl.22. A mixture according to claim 21, k characterized in that R-j_ in the acetanilide is methyl. 23. Blanding if0lge krav 22, kendetegnet ved, at acetanilidet er N-(ethoxymethyl)-2’ -trifluormethyl-6’-methyl-2-chloracetanilid.Composition according to claim 22, characterized in that the acetanilide is N- (ethoxymethyl) -2 '-trifluoromethyl-6'-methyl-2-chloroacetanilide. 24. Blanding ifelge krav 22, kendetegnet ved, at acetanilidet er N-(n-propoxymethyl)-2,-trifluormethyl- 20 6 *-methyl-2-chloracetanilid.Composition according to claim 22, characterized in that the acetanilide is N- (n-propoxymethyl) -2, -trifluoromethyl-6 * -methyl-2-chloroacetanilide. 25. Blanding if0lge krav 22, kendetegnet ved, at acetanilidet er N-(isopropoxymethyl)-2,-trifluormethyl-61-methyl-2-chloracetanilid.A composition according to claim 22, characterized in that the acetanilide is N- (isopropoxymethyl) -2, -trifluoromethyl-61-methyl-2-chloroacetanilide. 26. Blanding if0lge krav 22, kendetegnet ved, 25 at acetanilidet er N-(isobutoxymethyl)-2,-trifluormethyl- 61-methyl-2-chloracetanilid. 6i DK 15 718 9 BThe composition according to claim 22, characterized in that the acetanilide is N- (isobutoxymethyl) -2, -trifluoromethyl-61-methyl-2-chloroacetanilide. 6i DK 15 718 9 B 27. Blanding if0lge krav 21, kendetegnet ved, at R1 er ethyl.Mixture according to claim 21, characterized in that R 1 is ethyl. 28. Blanding if0lge krav 27, kendetegnet ved, at acetanilidet er N-(ethoxymethyl) - 2 '-trifluormethyl- 5 6,-ethyl-2-chloracetanilid.A composition according to claim 27, characterized in that the acetanilide is N- (ethoxymethyl) -2 '-trifluoromethyl-6,6-ethyl-2-chloroacetanilide. 29. Blanding i£0lge krav 27, kendetegnet ved, at acetanilidet er N-(n-propoxyraethyl)-2,-trifluormethyl-6f-ethyl-2-chloracetanilid.A composition according to claim 27, characterized in that the acetanilide is N- (n-propoxyacryethyl) -2, -trifluoromethyl-6f-ethyl-2-chloroacetanilide. 30. Blanding ifolge krav 27, kendetegnet ved, 10 at acetanilidet'er* N-(isopropoxymethyl)-2f-trifluorme- thyl-6’-ethyl-2-chloracetanilid.A composition according to claim 27, characterized in that acetanilide ether * N- (isopropoxymethyl) -2f-trifluoromethyl-6'-ethyl-2-chloroacetanilide. 31. Blanding ifolge krav 21, kendetegnet ved, at R·^ er hydrogen.Mixture according to claim 21, characterized in that R 2 is hydrogen. 32. Blanding ifolge krav 31, kendetegnet ved, 15 at acetanilidet er N-(isopropoxymetîiyl)-2,-trifluormethyl- 2-chloracetanilid.Composition according to claim 31, characterized in that the acetanilide is N- (isopropoxymethyl) -2, -trifluoromethyl-2-chloroacetanilide. 33. Blanding if0lge krav 20, kendetegnet ved, at R i acetanilidet er et alkenylradikal med op til 5 car-bonatorner.A composition according to claim 20, characterized in that R in the acetanilide is an alkenyl radical with up to 5 carbon towers. 34. Blanding ifolge krav 33, kendetegnet ved, at acetanilidet’ er N-(allyloxymethyl)-21 -trifluormethyl-6’-methyl-2-chloracetanilid.A composition according to claim 33, characterized in that the acetanilide 'is N- (allyloxymethyl) -21-trifluoromethyl-6'-methyl-2-chloroacetanilide. 35. Blanding ifelge krav 20, kendetegnet ved, 25 at R i acetanilidet er et alkynylradikal med op til 5 carbonatomer.The mixture according to claim 20, characterized in that R in the acetanilide is an alkynyl radical of up to 5 carbon atoms. 36. Blanding ifolge krav 35, kendetegnet ved, at acetanilidet er N-(propargyloxymethyl)-2’-trifluormethyl-6 *-methyl-2-chloracetanilid. DK 157189 BA composition according to claim 35, characterized in that the acetanilide is N- (propargyloxymethyl) -2'-trifluoromethyl-6 * -methyl-2-chloroacetanilide. DK 157189 B 37. Blanding ifolge krav 20, kendetegnet ved, at R i acetanilidet er et alkoxyalkylradikal med op til 5 carbonatorner.A composition according to claim 20, characterized in that R in the acetanilide is an alkoxyalkyl radical having up to 5 carbon atoms. 38. Blanding ifolge krav 37, kendetegnet ved, 5 at acetanilidet er N-(2-methoxyethoxyraethyl)-2’-trifluor- methyl-6’-methyl-2-chloracetanilid.38. A composition according to claim 37, characterized in that the acetanilide is N- (2-methoxyethoxy acid ethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide.