DK143831B - PROCEDURE FOR SELECTIVE PREVENTION OF WEEDS IN CROPS AND METHOD FOR EXERCISING THE PROCEDURE - Google Patents

Description

(19) DANMARK(19) DENMARK

|j| (12) FREMUEGGELSESSKRIFT od 143831 b| J | (12) PROCEDURAL WRITING OR 143831 b

DIREKTORATET FOR PATENT- OG VAREMÆRKEVÆSENETDIRECTORATE OF THE PATENT AND TRADEMARKET SYSTEM

(21) Ansøgning nr, 1183/75 (51) Intel.3 A 01 N 33/18 // (22) Indleveringsdag 20 . mar .1975 C 07 C 87/62 (24) Løbedag 20. mar. 1975 (41) Aim. tilgængelig 24. S ep. 1975 (44) Fremlagt 1 9 · okt. 1 981 (86) International ansøgning nr. “ (86) International indleveringsdag -(85) Videreførelsesdag -(62) Stamansøgning nr. -(21) Application No, 1183/75 (51) Intel.3 A 01 N 33/18 // (22) Filing Day 20. Mar.1975 C 07 C 87/62 (24) Running Day Mar 20 1975 (41) Aim. available 24. S ep. 1975 (44) Presented 1 9 · Oct. 1 981 (86) International application no. ”(86) International filing day - (85) Transfer day - (62) Master application no. -

(30) Prioritet 23. mar. 1974, 13028/74, GE(30) Priority Mar 23 1974, 13028/74, GE

(71) Ansøger LILLY INDUSTRIES LIMITED, London W1R 0PA, GB.(71) Applicant LILLY INDUSTRIES LIMITED, London W1R 0PA, GB.

(72) Opfinder Herschel Donovan Porter, US.(72) Inventor Herschel Donovan Porter, US.

(74) Fuldmægtig Th. Ostenfeld Patent bureau A/S.(74) Clerk Th. Ostenfeld Patent bureau A / S.

(54) Fremgangsmåde til selektiv bekæra= pelse af ukrudt i afgrøder og mld= del til udøvelse af fremgangsmåden.(54) Method of selectively mowing weeds in crops and target = part for carrying out the process.

Den foreliggende opfindelse angår en fremgangsmåde til selektiv bekæmpelse af ukrudt i afgrøder, samt et middel til udøvelse af fremgangsmåden.The present invention relates to a method of selectively controlling weeds in crops, and to a method of practicing the method.

Fremgangsmåden er ifølge opfindelsen ejendommelig ved, at der tilføres afgrødeområdet en herbicidt effektiv mængde af et 2,6-di-nitroanilinderivat med den almene formel IThe process according to the invention is characterized in that the crop area is fed with a herbicidally effective amount of a 2,6-di-nitroaniline derivative of the general formula I

0 CH, 0 R - N - CH-C = CH70 CH, 0 R - N - CH-C = CH7

Ό | 2 LΌ | 2 L

2 °2N—(I)2 ° 2N— (I)

1 V1 V

CF3 2 143831 hvori R betegner en ethyl-, propyl- eller allylgruppe, under de forudsætninger, at 2,6-dinitroanilinderivatet, når R betegner ethylgruppen, tilføres i en anden form end som et flydende præparat omfattende et N-aryl-N-alkoxyurinstofherbicid, eller som en blanding indeholdende en herbicidt aktiv 3-methylthio-4-amino-6-substitueret-l,2,4-tria-zin-5-on.CF3 2 143831 wherein R represents an ethyl, propyl or allyl group, provided that when the 2,6-dinitroaniline derivative, when R represents the ethyl group, is administered in a form other than as a liquid composition comprising an N-aryl-N-alkoxyurea herbicide or as a mixture containing a herbicidally active 3-methylthio-4-amino-6-substituted-1,2,4-triazin-5-one.

Der kendes mange 2,6-dinitroanilinderivater med herbicid aktivitet og især kendes der fra beskrivelsen til britisk patent nr. 1,348,428 herbicidt aktive forbindelser af denne type, der ligesom de ved fremgangsmåden ifølge opfindelsen anvendte forbindelser indeholder en trifluormethylgruppe i 4-stillingen. Det har uventet vist sig, at de ved fremgangsmåden ifølge opfindelsen anvendte 2,6-dinitroanilinderivater, som indeholder en 2-methylallylgruppe, har et bredt aktivitetsspektrum over for mange ukrudtstyper, herunder ukrudtstyper, som ikke vides at kunne bekæmpes med de fra britisk patentskrift nr. 1,348,428 kendte forbindelser. Det har også vist sig, at de ved fremgangsmåden ifølge opfindelsen anvendte forbindelser kan anvendes som eneste herbicidt aktive forbindelse, hvorimod man for andre 2,6-dinitroanilinderivaters vedkommende, herunder de i britisk patentskrift nr. 1,348,428 omhandlede, kræver samtidig tilstedeværelse af andre herbicidt aktive forbindelser.Many 2,6-dinitroaniline derivatives with herbicidal activity are known and in particular, from the specification of British Patent No. 1,348,428 herbicidal active compounds of this type are known, which, like the compounds used in the process according to the invention, contain a trifluoromethyl group at the 4-position. Unexpectedly, it has been found that the 2,6-dinitroaniline derivatives used in the process of the invention which contain a 2-methylallyl group have a broad spectrum of activity for many types of weeds, including weeds that are not known to be combated with those of British Patent Specification 1,348,428 known compounds. It has also been found that the compounds used in the process of the invention can be used as the only herbicide active compound, whereas for other 2,6-dinitroaniline derivatives, including those disclosed in British Patent Specification No. 1,348,428, the presence of other herbicide active compounds.

Ved fremgangsmåden ifølge opfindelsen foretrækkes det at anvende forbindelsen med den almene formel I, hvori R betyder ethylgruppen. Herved har det vist sig, at man kan bekæmpe ukrudtstyper af slægten Solanum, fx. Solanum nigrum, over for hvilken de mest aktive forbindelser ifølge britisk patentskrift nr. 1,348,428 ikke udviser nogen væsentlig aktivitet.In the process of the invention, it is preferred to use the compound of general formula I wherein R is the ethyl group. This has proved that we can fight weed types of the genus Solanum, e.g. Solanum nigrum, against which the most active compounds of British Patent Specification No. 1,348,428 show no significant activity.

Blandt forbindelserne med formel I er det ikke tidligere kendt at anvende forbindelsen, hvori R betegner en propylgruppe, til herbicide formål og et middel til udøvelse af fremgangsmåden ifølge opfindelsen er derfor ejendommeligt ved, at det indeholder et 2,6-di-nitroanilinderivat med formlen CH,Among the compounds of formula I, it is not previously known to use the compound wherein R represents a propyl group for herbicidal purposes and an agent for carrying out the process according to the invention is therefore characterized in that it contains a 2,6-di-nitroaniline derivative of the formula CH

LL

CH3-CH2-CH2 - n - CH2C = CH2 °2n_V\_n°2CH3-CH2-CH2 - n - CH2C = CH2 ° 2n_V \ _n ° 2

VV

CF3 3 1 A3 331CF3 3 1 A3 331

De omhandlede 2,6-dinitroanilinderivater kan fremstilles ved, at man omsætter et dinitrobenzenderivat med formlen x °2nV^N-/N°2 i X| CF3 hvori X betegner halogen, fortrinsvis chlor, med en amin med formlen fH3 R - NH - CH2 - C = CH2 hvori R har den ovenfor anførte betydning.The present 2,6-dinitroaniline derivatives can be prepared by converting a dinitrobenzene derivative of the formula x ° 2nV ^ N- / N ° 2 into X | CF3 wherein X represents halogen, preferably chlorine, with an amine of the formula fH3 R - NH - CH2 - C = CH2 wherein R is as defined above.

Syntesen foretages fortrinsvis i et organisk opløsningsmiddel eller et basisk vandigt medium, ved en temperatur fra 0°C til ca. 100°C eller højere. Reaktionstiderne varierer typisk fra ca. en time til ca. 24 timer afhængigt af temperaturen.The synthesis is preferably carried out in an organic solvent or a basic aqueous medium, at a temperature of from 0 ° C to approx. 100 ° C or higher. The reaction times typically range from approx. about one hour to approx. 24 hours depending on the temperature.

Alle de som udgangsmaterialer anvendte forbindelser til syntese af de omhandlede forbindelser er kommercielt tilgængelige eller kan fremstilles ved hjælp af metoder som kendes fra den kemiske litteratur.All of the compounds used as starting materials for the synthesis of the compounds of the invention are commercially available or can be prepared by methods known in the chemical literature.

Anvendelige organiske opløsningsmidler omfatter de aromatiske carbonhydrider såsom benzen og toluen, alkoholerne såsom ethanol og isopropanol, og andre for reaktionen inerte opløsningsmidler såsom tetrahydrofuran og dimethylsulfoxid. Et syrebindende middel såsom triethylamin bør sættes til det organiske opløsningsmiddel til absorbtion af hydrogen halogenidet (f.eks. HC1] som frigøres under reaktion. Reaktionen forløber også godt i basisk vandigt medium; den anvendte base er fortrinsvis natriumcarbonat, selvom andre baser såsom natriumhydroxid eller kaliumcarbonat også er anvendelige.Useful organic solvents include the aromatic hydrocarbons such as benzene and toluene, the alcohols such as ethanol and isopropanol, and other inert solvents such as tetrahydrofuran and dimethyl sulfoxide. An acid-binding agent such as triethylamine should be added to the organic solvent for absorption of the hydrogen halide (e.g., HCl] which is released during reaction. The reaction also proceeds well in basic aqueous medium; the base used is preferably sodium carbonate, although other bases such as sodium hydroxide or potassium carbonate is also useful.

Reaktionstemperaturen kan variere fra 0°C til ca. 100°C eller endog højere, når højtryksapparatur anvendes. Som sædvanligt er det mest hensigtsmæssigt at lade reaktionen forløbe ved tilbagesval ingstemperaturen for reaktionsblandingen. Ingen bireaktioner eller termisk nedbrydning opstår ved at gennemføre reaktionerne ved 4 143831 forhøjede temperaturer.The reaction temperature can range from 0 ° C to approx. 100 ° C or even higher when high pressure equipment is used. As usual, it is most convenient to allow the reaction to proceed at reflux temperature of the reaction mixture. No side reactions or thermal degradation occur by conducting the reactions at elevated temperatures.

I almindelighed nærmer reaktionerne sig deres afslutning med en hastighed, der afhænger af temperaturen. Således kan reaktionshastigheden forøges ved anvendelse af et højtkogende opløsningsmiddel for reaktionen og ved at arbejde ved tilbagesvalingstemperatur. En time er tilstrækkeligt til at fremstille et væsentligt udbytte af en vilkårlig af forbindelserne. Selv ved lave temperaturer er 24 timer tilstrækkeligt for at man nærmer sig maksimalt udbytte for en vilkårlig af forbindelserne.In general, the reactions are approaching their termination at a rate dependent on temperature. Thus, the reaction rate can be increased by using a high boiling solvent for the reaction and by operating at reflux temperature. One hour is sufficient to produce a substantial yield of any of the compounds. Even at low temperatures, 24 hours is sufficient to reach maximum yield for any of the compounds.

I overensstemmelse med den ovennævnte almene fremgangsmåde fremstilledes forbindelserne med formel I.In accordance with the above general procedure, the compounds of formula I.

Eksempel 1 N-Allyl-N-methallyl-4- trifluormethyl-2,6-dinitroanilin, smeltepunkt 53-54°C.Example 1 N-Allyl-N-methallyl-4-trifluoromethyl-2,6-dinitroaniline, mp 53-54 ° C.

Eksempel 2 N-Ethyl-N-methallyl-4- trifluormethyl-2,6-dinitroanilin, smeltepunkt S4-57°C.Example 2 N-Ethyl-N-methallyl-4-trifluoromethyl-2,6-dinitroaniline, m.p. S4-57 ° C.

Eksempel 3 N-Methallyl-N-propyl-4-trifluormethyl -2,6-dinitroanilin, smeltepunkt 41-43°C.Example 3 N-Methallyl-N-propyl-4-trifluoromethyl -2,6-dinitroaniline, mp 41-43 ° C.

Følgende herbicide test-metode anvendtes til undersøgelsen af de omhandlede forbindelser.The following herbicidal test method was used for the study of the subject compounds.

Den jord, hvori test-planterne voksede, var en blanding af lige store volumendele sand og en middel-svær topjord. Planterne dyrkedes i flade, galvaniserede stålskåle af en længde på 35 cm, en bredde på 25 cm og en dybde på 8 cm. Skålenes bunde var riflede og perforerede til dræning.The soil in which the test plants grew was a mixture of equal volumes of sand and a medium-heavy top soil. The plants were grown in flat, galvanized steel bowls of a length of 35 cm, a width of 25 cm and a depth of 8 cm. The bottoms of the dishes were grooved and perforated for drainage.

Test-forbindelsen formuleredes ved opløsning af 120 mg deraf i 2.5 ml af en opløsning indeholdende 10 g emulgeringsmidler i en blanding af 1 liter acetone og 1 liter ethanol. De 2,5 ml opløsning dipergeredes dernæst i 22,5 ml vand indeholdende 0.045¾ af emulgeringsmidlerne. Den vandige dispersion fortyndedes passende til fremstilling af præparater, der ville tilføre de rette mængder af test-forbindelse, når 12,5 ml dispersion påførtes hver flade.The test compound was formulated by dissolving 120 mg thereof in 2.5 ml of a solution containing 10 g of emulsifiers in a mixture of 1 liter of acetone and 1 liter of ethanol. The 2.5 ml solution was then dispersed in 22.5 ml of water containing 0.045¾ of the emulsifiers. The aqueous dispersion was suitably diluted to prepare compositions that would provide the right amounts of test compound when 12.5 ml of dispersion was applied to each surface.

5 143831 3,785 1 af jordblandingen anbragtes i hver skål og udglat-tedes. Frø af test-planterne plantedes i jorden i rækker vinkelret på skålens længdeakse og dækkedes med jord. Ca. en halv liter flydende gødningsmiddel indeholdende 2,5 g opløselig 18-25-18 gødning sattes til hver skål efter plantning.The soil mixture was placed in each dish and smoothed. Seeds of the test plants were planted in the soil in rows perpendicular to the longitudinal axis of the bowl and covered with soil. Ca. half a liter of liquid fertilizer containing 2.5 g of soluble 18-25-18 fertilizer was added to each bowl after planting.

Test-forbindelsen påførtes skålen samme dag frøene plantedes ved at sprøjte dispersionen af forbindelsen jævnt over jorden med en forstøversprøjte.The test compound was applied to the dish the same day the seeds were planted by spraying the dispersion of the compound evenly over the ground with an atomizer.

Efter behandling anbragtes skålene i et drivhus, der holdtes ved en temperatur og fugtighed, som var passende for planternes vækst. Planterne iagttoges 12 dage efter behandling, og hvert tilfælde tildeltes karakterer efter en skala fra 1 - 5. En karakter på 1 viser, at planterne spirede og voksene normalt, og en karakter på 5 viser, at planterne ikke spirede eller døde hurtigt efter spiring. Karakterer på 2, 3 eller 4 viser henholdsvis ringe, moderat eller kraftig skade. De ved afprøvning af forbindelserne ifølge opfindelsen opnåede resultater ved tilførselsmængder på ca. 1,135 og ca. 4,540 kg/hektar var følgende, idet forbindelserne er identificeret ved hjælp af nummeret på det tilsvarende eksempel ovenfor.After treatment, the dishes were placed in a greenhouse maintained at a temperature and humidity appropriate to the growth of the plants. The plants were observed 12 days after treatment, and each case was awarded on a scale of 1 - 5. A grade of 1 indicates that the plants germinated and waxed normally, and a grade of 5 indicates that the plants did not germinate or die quickly after germination. Grades of 2, 3 or 4 show minor, moderate or severe damage, respectively. The results obtained when testing the compounds of the invention at feed amounts of about 1.135 and approx. 4,540 kg / hectare was as follows, the compounds being identified by the number of the corresponding example above.

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Som det fremgår af foranstående data er fremgangsmåden ifølge opfindelsen sikker at anvende på mange økonomisk vigtige afgrøder, blandt hvilke bomuld, soyabønner og sukkerroer er særligt foretrukne. Andre afgrøder, hvorpå fremgangsmåden med fordel kan anvendes, omfatter kartoffel, tomat, tobak, løg, melon og agurk.As can be seen from the foregoing data, the method according to the invention is safe to apply to many economically important crops, among which cotton, soybeans and sugar beets are particularly preferred. Other crops for which the method can be used advantageously include potato, tomato, tobacco, onion, melon and cucumber.

Fremgangsmåden ifølge opfindelsen kan anvendes på mange u-krudtstyper, der angriber og skader ovennævnte og andre afgrøder, således som ovenstående data belyser. Andre ukrudtstyper, der formodes at kunne bekæmpes, omfatter Solanum nigrum, Chenopodium album, Polygenum convolvulus, Datura stramonium, Portulaca oleracea, Convolvulus arvensis, Fumaria officinalis, Echinochloa crus-galli, Setaria sp., Poa annua og Phalaris minor.The method of the invention can be applied to many weed types that attack and damage the above and other crops, as illustrated by the above data. Other types of weed that are believed to be controlling include Solanum nigrum, Chenopodium album, Polygenum convolvulus, Datura stramonium, Portulaca oleracea, Convolvulus arvensis, Fumaria officinalis, Echinochloa crus-galli, Setaria sp., Poa annua and Phalaris minor.

Blandt de ved fremgangmåden ifølge opfindelsen anvendte 2,6-dinitroanilinderivater med den almene formel I er den mest foretrukne forbindelse som nævnt den, hvori R betegner ethylgruppen, dvs. N-ethyl-N-2-methylallyl-4-trifluormethyl-2,6-dinitroanilin. Denne forbindelse sammenlignedes med forbindelser ifølge britisk patentskrift nr. 1,348,428, nemlig N,N-dipropyl-4-trifluormethyl- 2.6- dinitroanilin og N-butyl-N-ethyl-4-trifluormethyl-2,6-dinitroanilin over for Solanum nigrum.Among the 2,6-dinitroaniline derivatives of the general formula I used in the process of the invention, the most preferred compound mentioned is that wherein R represents the ethyl group, i.e. N-ethyl-N-2-methylallyl-4-trifluoromethyl-2,6-dinitroaniline. This compound was compared to compounds of British Patent Specification No. 1,348,428, namely N, N-dipropyl-4-trifluoromethyl-2,6-dinitroaniline and N-butyl-N-ethyl-4-trifluoromethyl-2,6-dinitroaniline to Solanum nigrum.

De aktive bestanddele inkorporeredes i jorden før plantning af afgrøder af hhv. jordnødder og bomuld. X jordnødder gav forbindelsen N-ethyl-N-2-methylallyl-4-trifluormethyl-2,6-dinitroanilin ifølge opfindelsen en bekæmpelse af Solanum nigrum på 100% ved en tilført mængde på 1,25 kg/ha, mens den kendte forbindelse N-bu-tyl-N-ethyl-4-trifluormethyl-2,6-dinitroanilin gav en bekæmpelse af Solanum nigrum på 791 ved en tilført mængde på 1,15 kg/ha. I bomuld gav den før nævnte forbindelse ifølge opfindelsen en bekæmpelse af Solanum nigrum på 871 ved en tilført mængde på 1,0 kg/ ha, mens den kendte forbindelse N,N-dipropyl-4-trifluormethyl- 2.6- dinitroanilin gav en bekæmpelse af Solanum nigrum på 55% ved en tilført mængde på 1,0 kg/ha.The active ingredients were incorporated into the soil before planting crops of respectively. peanuts and cotton. X peanuts gave the compound N-ethyl-N-2-methylallyl-4-trifluoromethyl-2,6-dinitroaniline according to the invention a control of Solanum nigrum of 100% at an applied rate of 1.25 kg / ha, while the known compound N -Butyl-N-ethyl-4-trifluoromethyl-2,6-dinitroaniline gave a control of Solanum nigrum of 791 at an applied rate of 1.15 kg / ha. In cotton, the aforementioned compound of the invention gave a control of Solanum nigrum of 871 at an applied rate of 1.0 kg / ha, while the known compound N, N-dipropyl-4-trifluoromethyl-2,6-dinitroaniline gave a control of Solanum nigrum of 55% at an applied rate of 1.0 kg / ha.

I almindelighed er det bedst at tilføre forbindelserne inden afgrødefrøene plantes, men efter at afgrødeområdet er blevet gjort klart til plantning. Det er sædvanligvis mest effektivt at inkorporere forbindelsen i jordens toplag ved at blande jorden med et redskab såsom en roterende hakke, rullende kultivator eller pladeharve efter at forbindelsen er tilført markjorden. Inkorporerings-redskabet bør blande forbindelsen i et jordlag af fra ca, 5 cm til ca. 15 cm dybde.In general, it is best to add the compounds before the crop seeds are planted, but after the crop area has been made clear for planting. It is usually most effective to incorporate the compound into the top layer of the soil by mixing the soil with a tool such as a rotary pick, rolling cultivator or plate harrow after the compound is applied to the soil. The incorporation tool should mix the compound in a soil layer of from about 5 cm to approx. 15 cm depth.

8 143831 I det mindste en herbicidt effektiv mængde af forbindelsen skal tilføres afgrødeområdet. I almindelighed ligger effektive herbicide mængder i intervallet mellem ca. 0,28 og ca. 11,35 kg/ha.At least one herbicide effective amount of the compound should be applied to the crop area. In general, effective herbicidal amounts are in the range of about 0.28 and approx. 11.35 kg / ha.

Det foretrukne interval for den tilførte mængde er på ca. 0,57 til ca. 4,54 kg/ha. Det vil være indlysende for formanden at mængder, der enten ligger under eller over det anførte interval, til tider kan være nødvendige for at opnå de bedste resultater i praksis.The preferred range for the amount supplied is about 0.57 to approx. 4.54 kg / ha. It will be obvious to the President that quantities that are either below or above the stated range may sometimes be necessary to achieve the best results in practice.

Fremgangsmåden ifølge opfindelsen bekæmper væksten af ukrudtsspirer og spiringen af ukrudt i et omfang, der afhænger af ukrudtsarten og identiteten og mængderne af de tilførte forbindelser. I nogle tilfælde udryddes, som det fremgår af ovenstående herbicide testdata, hele mængden af ukrudt. I andre tilfælde beskadiges det spirende ukrudt kun, eller en del af ukrudtet dræbes, og en del beskadiges. Beskadigelsen af en ukrudtsspire, som vokser i et opdyrket område, er meget gunstig for afgrøden, fordi de normalt voksende afgrødeplanter skygger og får det langsomt voksende ukrudt til at visne. Skyggeeffekten af afgrøden er særlig vigtig ved en buskagtig afgrøde såsom bomuld eller en vilkårlig af bønne-familien.The method of the invention combats the growth of weed germs and the germination of weeds to an extent that depends on the weed species and the identity and quantities of the compounds applied. In some cases, as shown in the above herbicidal test data, the entire amount of weeds is eradicated. In other cases, the germinating weeds are only damaged or some of the weeds are killed and some are damaged. The damage to a weed seed growing in a cultivated area is very favorable to the crop because the normally growing crop plants shade and cause the slow growing weeds to wither. The shading effect of the crop is particularly important in a bushy crop such as cotton or any of the bean family.

Selvom forbindelserne kan tilføres det opdyrkede område i ren form, er det mest hensigtsmæssigt at tilføre dem i form af herbicide præparater. De herbicide præparater indeholder en eller flere af de omhandlede forbindelser kombineret med mindst én inert bærer. De inerte bærere kan enten være flydende eller faste.Although the compounds can be applied to the cultured area in pure form, it is most convenient to administer them in the form of herbicidal preparations. The herbicidal compositions contain one or more of the subject compounds combined with at least one inert carrier. The inert carriers can be either liquid or solid.

Inerte bærere som indgår i præparaterne og fremgangsmåder til fremstilling af præparaterne er sådanne, der er konventionelle inden for den landbrugstekniske kemi. En vis forklaring på formuleringen af de omhandlede herbicide præparater vil alligevel blive givet for at sikre at de bedste udførelsesformer fremgår klart.Inert carriers included in the compositions and methods of preparing the compositions are those conventional in the field of agricultural chemistry. Nevertheless, some explanation of the formulation of the herbicidal compositions in question will be provided to ensure that the best embodiments are clear.

Meget ofte formuleres forbindelserne som koncentrerede præparater for tilførsel til jorden i form af vandige dispersioner eller emulsioner, der indeholder fra ca. 0,1¾ til ca..l% af forbindelsen. Vanddispergérbare eller emulgerbare præparater er enten findelte faste stoffer sædvanlig kendt som befugtelige pulvere, eller vædsker sædvanligvis kendt som emulgerbare koncentrater.Very often, the compounds are formulated as concentrated preparations for application to the soil in the form of aqueous dispersions or emulsions containing from ca. 0.1 to about 1% of the compound. Water dispersible or emulsifiable compositions are either finely divided solids usually known as wettable powders, or liquids usually known as emulsifiable concentrates.

Herbicide befugtelige pulvere omfatter en intim blanding af den aktive forbindelse, en inert bærer og overfladeaktive midler. Koncentrationen af den aktive forbindelse er sædvanligvis fra ca.Herbicidal wettable powders include an intimate mixture of the active compound, an inert carrier and surfactants. The concentration of the active compound is usually from ca.

10¾ til ca. 90¾. Den inerte bærer er sædvanligvis udvalgt blandt attapulgit-lertyperne, montmorillonit-lertyperne, diatome-jordty- 143831 9 perne eller de rensede silicater. Effektive overfladeaktive midler, der udgør fra ca. 0,5¾ til ca. 10¾ af det befugtelige pulver, findes blandt de sulfonerede ligniner, de kondenserede naphthalin-sulfonater, naphthalinsulfonaterne, alkylbenzensulfonaterne, alkyl-sulfaterne og ikke-ioniske overfladeaktive midler såsom ethylenoxid-additionsforbindelser med phenol.10¾ to approx. 90¾. The inert carrier is usually selected from the attapulgite clays, montmorillonite clays, diatomaceous earth types or the purified silicates. Effective surfactants comprising from approx. 0.5¾ to approx. 10¾ of the wettable powder is found among the sulfonated lignins, the condensed naphthalene sulfonates, the naphthalene sulfonates, the alkyl benzene sulfonates, the alkyl sulfates and nonionic surfactants such as ethylene oxide addition compounds with phenol.

Typiske herbicide emulgerbare koncentrater af forbindelserne omfatter en bekvem koncentration af den aktive forbindelse, såsom fra ca. 50 til ca. 600 g/1 væske, opløst i en inert bærer såsom en blanding af vand-ublandbart organisk opløsningsmiddel og emulgeringsmidler. Det organiske opløsningsmiddel udvælges med hensyn til dets opløsningsevne og dets pris.Typical herbicidal emulsifiable concentrates of the compounds comprise a convenient concentration of the active compound, such as from ca. 50 to approx. 600 g / l of liquid dissolved in an inert carrier such as a mixture of water-immiscible organic solvent and emulsifiers. The organic solvent is selected for its solubility and its cost.

Anvendelige organiske opløsningsmidler omfatter aromaterne, specielt xylenerne, og af jordoliefraktionerne, specielt de højt-kogende naphthaleniske og olefiniske dele af jordolie såsom tung aromatisk naphtha. Andre organiske opløsningsmidler kan også anvendes såsom de terpeniske opløsningsmidler, herunder kolofonium-derivater. Emulgeringsmidler, der udgør ca. 0,5 til ca. 10¾ af de emulgerbare koncentrater, udvælges blandt de samme typer overfladeaktive midler, som anvendtes til befugtelige pulvere.Useful organic solvents include the aromatics, especially the xylenes, and of the petroleum fractions, especially the high-boiling naphthalene and olefinic portions of petroleum such as heavy aromatic naphtha. Other organic solvents may also be used such as the terpenic solvents, including rosin derivatives. Emulsifiers which constitute approx. 0.5 to approx. 10¾ of the emulsifiable concentrates are selected from the same types of surfactants used for wettable powders.

Granulære præparater er også hensigtsmæssige formler for tilførsel af forbindelserne ved simpel fordeling af præparatet jævnt over det opdyrkede område. Herbicide granulater omfatter typisk en forbindelse dispergeret på en granulær inert bærer, for hvilken groft malet ler er typisk. Partikelstørrelsen af sådanne granulater varierer sædvanligvis fra ca. 0,1 til ca. 3 mm. Den sædvanlige formuleringsproces omfatter opløsning af forbindelsen i et opløsningsmiddel såsom petroleum eller svær aromatisk naphtha, og tilførselen af opløsningen til bæreren i en passende blander. Mindre økonomisk kan forbindelsen dispergeres i en dej sammensat af fugtigt ler eller en anden bærer, hvilken dej dernæst tørres og formales groft til fremstilling af det ønskede granulære produkt.Granular compositions are also suitable formulas for supplying the compounds by simple distribution of the composition evenly over the cultured area. Herbicidal granules typically comprise a compound dispersed on a granular inert carrier for which coarse painted clay is typical. The particle size of such granules usually ranges from approx. 0.1 to approx. 3 mm. The usual formulation process involves dissolving the compound in a solvent such as petroleum or heavy aromatic naphtha, and feeding the solution to the carrier in a suitable mixer. Less economically, the compound can be dispersed in a dough composed of moist clay or another support, which dough is then dried and coarsely ground to produce the desired granular product.

De herbicide præparater kan tilføres det opdyrkede område ved anvendelsen af konventionelt apparatur. For eksempel kan vand-dispergerede præparater påføres ved hjælp af sprøjtemidler, der kan være håndbårne,traktormonterede, selvdrivende eller trukne. Granulære præparater kan påføres ved hjælp af en vilkårlig blandt mange 10 143831 påføringsmidler, der nu er i almindelig brug. Operatøren af tilførselsapparaturet behøver blot at drage omsorg for at tilføre en mængde af præparatet pr. hektar, som tilfører den ønskede mængde af forbindelsen, og at tilføre den jævnt over hele det opdyrkede område.The herbicidal compositions can be applied to the cultured area using conventional apparatus. For example, water-dispersed compositions may be applied by spraying agents which may be hand-borne, tractor-mounted, self-propelled or towed. Granular compositions can be applied by any of many commonly applied applicants. The operator of the feeder only needs to take care to supply an amount of the preparation per day. per hectare, which supplies the desired amount of compound and to apply it evenly throughout the cultivated area.

De herbicide præparater kan som eneste aktive bestanddel indeholde en forbindelse med formel I. Alternativt kan de også indeholde andre herbicider såsom urinstof-herbicider, f.eks.The herbicidal compositions may contain as a single active ingredient a compound of formula I. Alternatively, they may also contain other herbicides such as urea herbicides, e.g.

3-(3,4-dichlorphenyl)-1-methoxy-l-methylurinstof, 3-(4-chlorphenyl)- 1- methoxy-l-methylurinstof; 3-C4-bromphenyl)-1-methoxy-l-methyl-urinstof; 3-(3,4-dichlorphenyl)-l,l-dimethylurinstof; Ν'-4-(4-chlor-phenoxy)phenyl-N,N-dimethylurinstof, og N'-(3-chlor-4-methoxyphenyl)-Ν,Ν-dimethylurinstof; triazin-herbicider såsom 2-chlor-4-ethylamino--6-isopropylamino-l,3,5-triazin; 2-chlor-4,6-bis(ethylamino)-l,3,5-triazin; 4-ethylamino-2-methylthio-6-t-butylamino-l,3,5-triazin; phenoxy-herbicider såsom 4-(2,4-dichlor-phenoxy)-smørsyre; 4-(4-chlor- 2- methylphenoxy)-smørsyre og 2-[(4-chlor-o-tolyl)oxy]-propionsyre; carbamat-herbicider såsom isopropyl-N-(3-chlorphenyl)carbamat; amid-herbicider såsom N-(4-chlorphenyl)-2,2-dimethyl-valeramid og 2-(a-naphthoxy)-Ν,Ν-diethyl-propionamid; eller herbicider såsom 2-(1-methyl-n-propyl)-4,6-dinitrophenol; 3,5-dinitro-N,N-dipropyl-sulphanilamid; 5-amino-4-chlor-2-phenyl-3-pyridazon og l-(5-t-butyl- l,3,4-thiadiazol-2-yl)-l,3-dimethylurinstof og thiolcarbamat-herbicider såsom S-ethyl-N,N-dipropylthiocarbamat.3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea, 3- (4-chlorophenyl) -1-methoxy-1-methylurea; 3-C 4-bromophenyl) -1-methoxy-l-methyl-urea; 3- (3,4-dichlorophenyl) -l, l-dimethylurea; Ν'-4- (4-chloro-phenoxy) phenyl-N, N-dimethylurea, and N '- (3-chloro-4-methoxyphenyl) -Ν, Ν-dimethylurea; triazine herbicides such as 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine; 2-chloro-4,6-bis (ethylamino) -l, 3,5-triazine; 4-ethylamino-2-methylthio-6-t-butylamino-l, 3,5-triazine; phenoxy herbicides such as 4- (2,4-dichloro-phenoxy) -butyric acid; 4- (4-chloro-2-methylphenoxy) -butyric acid and 2 - [(4-chloro-o-tolyl) oxy] -propionic acid; carbamate herbicides such as isopropyl N- (3-chlorophenyl) carbamate; amide herbicides such as N- (4-chlorophenyl) -2,2-dimethyl-valeramide and 2- (α-naphthoxy) -Ν, Ν-diethyl-propionamide; or herbicides such as 2- (1-methyl-n-propyl) -4,6-dinitrophenol; 3,5-dinitro-N, N-dipropyl-sulphanilamid; 5-amino-4-chloro-2-phenyl-3-pyridazone and 1- (5-t-butyl-1,3,4-thiadiazol-2-yl) -1,3-dimethylurea and thiolcarbamate herbicides such as S ethyl-N, N-dipropylthiocarbamate.