DE1079885B - Means for combating unwanted plant growth - Google Patents

Means for combating unwanted plant growth

Info

Publication number
DE1079885B
DE1079885B DEB51896A DEB0051896A DE1079885B DE 1079885 B DE1079885 B DE 1079885B DE B51896 A DEB51896 A DE B51896A DE B0051896 A DEB0051896 A DE B0051896A DE 1079885 B DE1079885 B DE 1079885B
Authority
DE
Germany
Prior art keywords
acid
plant growth
unwanted plant
tetrachloro
salts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DEB51896A
Other languages
German (de)
Inventor
Dr Friedrich Becke
Dr Herbert Bittermann
Dr Adolf Fischer
Dr Herbert Stummeyer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DEB51896A priority Critical patent/DE1079885B/en
Publication of DE1079885B publication Critical patent/DE1079885B/en
Pending legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02Aryloxy-carboxylic acids; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N2300/00Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Description

=Mittel -zur Bekämpfung unerwünschten.-Pflanzenwachstums- ° ° Als Mittel zur Bekämpfung von Ackerunkräutern, besonders in Getreidekulturen, sind verschiedene Verbindungen bekannt, die äber zum Teil nicht alle Unkräuter vernichten.-Dies gilt vor. allein für die 2,4-Dichlorphenä,xyessigsäure, die2-Methyl-4-chförphenoxyessigsäüri# . ünd'--die. :Z,.4.,5-Trichlorplienoxpessigsäure und ihre: Salze,- die in großem -Xdßstab zur Bekämpfüng-von-Getreideunkräutern verwendet werden, aber geggen:das Klettenlabkraut (Galiürsi apariney-unwirksam sind, so daß sich dieses lästige Unkraut im Laufe der Zeit stark vermehrt hat. tderdings ist die 2-Methyl-4,chlötphenoxy-a=propinnsäure- zur. .Bekämpfung dieses Unkrauts herangezogen vvord'en,` afier da das synthetAche Prodükf ein Räcexnat°isf, während pflanzenliÜysiölogisch- nul:'' eine der b.eideh s-teieoisomeren Formen wirksam ist, braucht man verhältnismäßig große Metzgen . Uieser. Verbixidung,--.üzri das Klettenlabkraut zu vernichten, wodurch ihre Anwendung verteuert wird.= Means -for combating undesired.-plant growth- ° ° As Means for controlling arable weeds, especially in cereal crops, are various Known compounds which in part do not destroy all weeds.-This applies before. only for 2,4-dichlorophena, xyacetic acid, 2-methyl-4-chförphenoxyessigsäüri # . ünd '- the. : Z, .4., 5-Trichlorplienoxpessigsäure and its: salts, - which in large -Xdßstab can be used to control cereal weeds, but against: that Klettenlabkraut (Galiürsi apariney-are ineffective, so that this annoying weed has increased significantly over time. However, 2-methyl-4, chlorophenoxy-a = propinic acid to the. .Fighting this weed is used in the front, `afier da das synthetAche Prodükf a Räcexnat ° isf, while plant liÜysiölogisch- nul: '' one of the b.eideh s-teieoisomeric forms is effective, one needs relatively large butchers. Uieser. Verbixierung, -. Üzri to destroy the burdock weed, thereby reducing their application becomes more expensive.

Weiterhin sind chlorierte Benzoesäuren, wie die 2,3,5,6-Tetrachlorbenzoesäure und die 2,3,6-Trichlorbenzoesäure sowie deren Salze oder Derivate, als Unkrautbekämpfungsmittel bekannt, die gegen Dikotyle wirksam sind und auch das gegen die üblichen Mittel resistente Klettenlabkraut vernichten. Sie besitzen aber den großen Nachteil, daß sie am Getreide Wuchsschäden hervorrufen. Ihre allgemeine Anwendung ist daher, mit einem Risiko verbunden, so daß ihre Verwendung nur für wenige Spezialzwecke in Frage kommt.There are also chlorinated benzoic acids, such as 2,3,5,6-tetrachlorobenzoic acid and 2,3,6-trichlorobenzoic acid and its salts or derivatives as weed control agents known that are effective against dicots and also against the usual means destroy resistant burdock weeds. But they have the big disadvantage that they cause growth damage in the grain. Their general application, therefore, is with associated with a risk, so that their use for a few special purposes is only in question comes.

Es ist ferner, bekannt, Alkylbenzoesäuren, Halogenalkylbenzoesäuren, Aminobenzoesäuren und Halogenbenzoylbenzoesäuren sowie deren Salze oder Derivate zur Bekämpfung unerwünschten Pflanzenwachstums zu verwenden. Diese Verbindungen haben aber zum Teileine schlechte Wirkung auf das Unkraut oder, soweit sie eine gute Wirkung entfalten, hemmen sie das Wachstum des Getreides.It is also known, alkylbenzoic acids, haloalkylbenzoic acids, Aminobenzoic acids and halobenzoylbenzoic acids and their salts or derivatives to use to combat unwanted plant growth. These connections but sometimes have a bad effect on the weeds or, if they have one work well, they inhibit the growth of the grain.

Es wurde nun gefunden, daß die 2,3,5,6-Tetrachlor-4-methylbenzoesäure eine hervorragende herbicide Wirkung gegen Dikotyle, einschließlich der gegen die üblichen Unkrautvernichtungsmittel resistenten Arten, wie Klettenlabkraut, besitzt, ohne dabei Wuchsschäden am Getreide hervorzurufen. Die Verbindung zeigt sich z. B. wirksam gegen: Matricaria chamomilla, Raphanus raphanistrum, Stellaria media, Lamium amplexicaule, Galeopsis tetrahit, Chenopodium album, Galium aparine, Mercurialis annua und Sinapis arvensis.It has now been found that 2,3,5,6-tetrachloro-4-methylbenzoic acid excellent herbicidal activity against dicots, including against the common weedkiller-resistant species, such as burdock weed, without causing growth damage to the grain. The connection shows up e.g. B. effective against: Matricaria chamomilla, Raphanus raphanistrum, Stellaria media, Lamium amplexicaule, Galeopsis tetrahit, Chenopodium album, Galium aparine, Mercurialis annua and Sinapis arvensis.

Diese Wirkung war nicht vorauszusehen, denn die 2,3,4,6-Tetrachlorbenzoesäure, die 2,3,4,5-Tetrachlorbenzoesäure und die 2,4,5-Trichlorbenzoesäure sind als Herbicide praktisch unwirksam, so daß die Vermutung naheliegt, daß für die pflanzenphysiologische Wirksamkeit der Tri- und Tetrachlorbenzoesäuren die freie, nur durch Wasserstoff besetzte Para-Stellung im Phenylkern der chlorierten Benzoesäure notwendig ..ist. Auch die 2,3,5-Trichlorbenzoesäure besitzt, entsprechend dieser Vermutung, herbicide Eigenschaften.This effect could not be foreseen, because the 2,3,4,6-tetrachlorobenzoic acid, 2,3,4,5-tetrachlorobenzoic acid and 2,4,5-trichlorobenzoic acid are herbicides practically ineffective, so that the assumption is that for the plant physiological Effectiveness of the tri- and tetrachlorobenzoic acids the free, only by hydrogen occupied para position in the phenyl nucleus of chlorinated benzoic acid .. is necessary. According to this assumption, 2,3,5-trichlorobenzoic acid also has herbicides Properties.

Die herbicide Wirksamkeit der 2,3,5,6-Tetrachlorp-toluylsäure liegt in der gleichen Größenordnung wie bei den üblichen herbiciden Substanzen. Mit der neuen Verbindung werden praktisch alle Ackerunkräuter vernichtet, ohne daß das Getreide geschädigt wird. Die Anwendung der 2,3,5,6-Tetrachlor-4-methylbenzoesäure wird in den nachstehenden Beispielen erläutert. Beispiel 1 Etwa 10 bis 12 cm lange Klettenlabkrautpflanzen (2. bis 3. Laubblattrosette) werden mit dem Natriumsalz der 2,3,5,6-Tetrachlor-p-toluylsäure in Wirkstoffmengen von 2 bis 4 kg in 1'Q001 Wasser je Hektar besprüht. Nach einigen Tagen krümmen sich die Blätter, besonders an den Vegetationsspitzen, nach unten zum Stengel hin. Die Pflanzen bleiben in ihrem Wachstum zurück und setzen an den neuen Trieben nur ganz kleine Blättchen an. Nach 4 Wochen sind sie teilweise abgestorben. Nahezu dieselbe Wirkung erreicht man, wenn man statt des Natriumsalzes der 2,3,5,6-Tetrachlor-p-toluylsäure das 2,3,5,6-Tetrachlor-p-toluylsäureamid oder den 2,3,5,6-Tetrachlor-p-toluylsäurebutylglykolester anwendet.The herbicidal effectiveness of 2,3,5,6-tetrachlorop-toluic acid lies in the same order of magnitude as with the usual herbicidal substances. With the new connection practically all arable weeds are destroyed, without the grain is harmed. The application of 2,3,5,6-tetrachloro-4-methylbenzoic acid is described in the examples below. Example 1 Burdock weed plants about 10 to 12 cm long (2nd to 3rd rosette of leaves) are treated with the sodium salt of 2,3,5,6-tetrachloro-p-toluic acid Sprayed in amounts of active ingredient of 2 to 4 kg in 1'Q001 water per hectare. After some Days, the leaves curve down, especially at the tops of the vegetation towards the stem. The plants lag behind in their growth and continue to grow only very small leaflets on new shoots. Some of them died after 4 weeks. Almost the same effect is achieved if you use 2,3,5,6-tetrachloro-p-toluic acid instead of the sodium salt 2,3,5,6-tetrachloro-p-toluic acid amide or 2,3,5,6-tetrachloro-p-toluic acid butyl glycol ester applies.

Beispiel 2 2,3,5,6-Tetrachlor-p-toluylsäure-Natriumsalz (I) wird mit einer Menge von 2 kg im Vergleich zu 2 kg 2,3,6-Trichlorbenzoesäure-Natriumsalz (II) und 2 kg 2,3,5,6-Tetrachlorbenzoesäure-Natriumsalz (III) in je 10001 Wasser je Hektar auf Hafer, Weizen, Senf und Klettenlabkraut gespritzt. Nach 10 Wochen läßt sich feststellen, daß Senf und Klettenlabkraut nahezu vollkommen abgestorben sind. Die Hafer- und Weizenpflanzen machen nach der Anwendung von II und III einen gestauchten und zerzausten Eindruck, während sie bei I normal aussehen. Die genauen Werte für die herbicide Wirkung sind aus der nachfolgenden Tabelle ersichtlich: Substanz Hafer Weizen Senf Kletten- labkraut I . . . . . . . . . . . . 0 0 4 bis 5 4 II . . . . . . . . . . . . 3 bis 4 3 4 bis 5 4 bis 5 III ............ 3 3 4 bis 5 4 Bonitierungssdiema: 0 = ohne Beschädigung. 1 = einzelne Blätter mit ganz geringen Schäden. 2 = wenige Schäden oder Hemmung der meisten Pflanzen. 3 = starke Schäden, Blätter aber nicht absterbend, ganze Pflanze geschädigt. 4 = größter Teil der Blätter und auch einzelne Pflanzen abge- storben. 5 = Pflanzen völlig vernichtet. Beispiel 3 In einem Feldbestand mit Wintergerste wird im Spätherbst eine verunkrautete 2-qm-Parzelle mit einer Lösung des Natriumsalzes der 2,3,5,6-Tetrachlorp-toluylsäure behandelt, »die der Anwendung einer Menge von 3 kg des Salzes in 6001 Wasser je Hektar entspricht. Nach 3 Wochen wird eine charakteristische Blatt- und Stengelverkrümmung der zweikeimblätterigen- Unkräuter beobachtet. Nach weiteren 2 Wochen beginnen folgende Unkrautpflanzen abzusterben: Matricaria chamomilla, Raphanus raphanistrum, Stellaria media, Lamium amplexicaule, Galeopsis tetrahit, Chenopidium album, Galium aparine, Mercurialis annua und Sinapis arvensis.Example 2 2,3,5,6-Tetrachloro-p-toluic acid sodium salt (I) is added in an amount of 2 kg compared to 2 kg 2,3,6-trichlorobenzoic acid sodium salt (II) and 2 kg 2,3 , 5,6-tetrachlorobenzoic acid sodium salt (III) sprayed in 10001 water per hectare on oats, wheat, mustard and burdock. After 10 weeks it can be determined that mustard and burdock have almost completely died. The oat and wheat plants make a compressed and disheveled impression after applying II and III, while they look normal with I. The exact values for the herbicidal effect can be seen in the following table: substance oats Wheat mustard burdock bedstraw I. . . . . . . . . . . . 0 0 4 to 5 4 II. . . . . . . . . . . . 3 to 4 3 4 to 5 4 to 5 III ............ 3 3 4 to 5 4 Credit rating: 0 = without damage. 1 = individual leaves with very little damage. 2 = little damage or inhibition of most plants. 3 = severe damage, leaves but not dying, whole plant damaged. 4 = largest part of the leaves and also individual plants died. 5 = plants completely destroyed. Example 3 In late autumn a weed-covered 2 square meter plot of land with winter barley is treated with a solution of the sodium salt of 2,3,5,6-tetrachlorop-toluic acid, using an amount of 3 kg of the salt in 600 liters of water per hectare. After 3 weeks, a characteristic curvature of the leaves and stems of the dicotyledonous weeds is observed. After a further 2 weeks, the following weed plants begin to die: Matricaria chamomilla, Raphanus raphanistrum, Stellaria media, Lamium amplexicaule, Galeopsis tetrahit, Chenopidium album, Galium aparine, Mercurialis annua and Sinapis arvensis.

Eine ähnliche Wirkung wie im Beispiel 3 wird durch die Anwendung folgender Mischung je Hektar erzielt: 1,1 kg 2-Methyl-4-chlorphenoxyessigsäure-Na-Salz -I- 1,9 kg 2',3,6-Trichlor-p-toluyl-Na-Salz.An effect similar to that in Example 3 is obtained by using the following Mixture per hectare achieved: 1.1 kg of 2-methyl-4-chlorophenoxyacetic acid Na salt -I- 1.9 kg of 2 ', 3,6-trichloro-p-toluyl Na salt.

Claims (2)

PATENTANSPRÜCHE: 1. Mittel zur Bekämpfung unerwünschten Pflanzenwachstums, gekennzeichnet durch einen Gehalt an- 2,3,5,6-Tetrachlor-4-methylbenzoesäure oder deren Salzen, Estern oder Amiden. PATENT CLAIMS: 1. Means for controlling unwanted plant growth, characterized by a content of 2,3,5,6-tetrachloro-4-methylbenzoic acid or their salts, esters or amides. 2. Mittel nach Anspruch 1, dadurch gekennzeichnet, daß es zusätzlich noch 2,4-Dichlorphenoxyessigsäure oder -pröpionsäure oder, -buttersäure oder 2-Methyl-4-chlorphenoxyessigsäure oder deren Salze, Ester oder Amide enthält. In Betracht gezogene Druckschriften: Deutsche Patentschriften Nr. 747 96-1, 860 639, 1019 32'4, 1032 971, 1046 394; österreichische Patentschrift Nr. 200 387; französische Patentschriften Nr. 1125 728, 1047 895; USA.-Patentschrift Nr. 2 322 760.2. Agent according to claim 1, characterized in that it additionally contains 2,4-dichlorophenoxyacetic acid or propionic acid or butyric acid or 2-methyl-4-chlorophenoxyacetic acid or salts, esters or amides thereof. Considered publications: German Patent Nos. 747 96-1, 860 639, 1019 32'4, 1032 971, 1046 394; Austrian Patent No. 200,387; French Patent Nos 1125728, 1047 895th; U.S. Patent No. 2,322,760.
DEB51896A 1959-01-29 1959-01-29 Means for combating unwanted plant growth Pending DE1079885B (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1276402B (en) * 1961-01-05 1968-08-29 Shell Res Ltd Herbicidal agents containing halothiobenzamides

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2322760A (en) * 1942-02-20 1943-06-29 Du Pont Composition and method
DE747961C (en) * 1941-05-09 1944-10-23 Promotion of plant growth
DE860639C (en) * 1944-05-19 1952-12-22 Hoechst Ag Influencing plant growth
FR1047895A (en) * 1950-07-15 1953-12-17 Bataafsche Petroleum Composition and method of weed control
FR1125728A (en) * 1954-06-04 1956-11-06 Diamond Alkali Co Body compositions, process for their preparation and their applications, more particularly for regulating plant growth
AT200387B (en) * 1956-09-03 1958-10-25 Fisons Pest Control Ltd Methods and means of weed killing

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE747961C (en) * 1941-05-09 1944-10-23 Promotion of plant growth
US2322760A (en) * 1942-02-20 1943-06-29 Du Pont Composition and method
DE860639C (en) * 1944-05-19 1952-12-22 Hoechst Ag Influencing plant growth
FR1047895A (en) * 1950-07-15 1953-12-17 Bataafsche Petroleum Composition and method of weed control
FR1125728A (en) * 1954-06-04 1956-11-06 Diamond Alkali Co Body compositions, process for their preparation and their applications, more particularly for regulating plant growth
AT200387B (en) * 1956-09-03 1958-10-25 Fisons Pest Control Ltd Methods and means of weed killing

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1276402B (en) * 1961-01-05 1968-08-29 Shell Res Ltd Herbicidal agents containing halothiobenzamides

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