DE1019324B - Preparations for influencing plant growth - Google Patents
Preparations for influencing plant growthInfo
- Publication number
- DE1019324B DE1019324B DED20595A DED0020595A DE1019324B DE 1019324 B DE1019324 B DE 1019324B DE D20595 A DED20595 A DE D20595A DE D0020595 A DED0020595 A DE D0020595A DE 1019324 B DE1019324 B DE 1019324B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- plant growth
- influencing plant
- preparations
- influencing
- 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
Links
- 230000008635 plant growth Effects 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- -1 oxymethyl Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- FUXMTEKFGUWSNC-UHFFFAOYSA-N 2,3,4,5-tetrachlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl FUXMTEKFGUWSNC-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 208000012868 Overgrowth Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003123 plant toxin Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, 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
- A01N37/42—Biocides, 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 within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Mittel zur Beeinflussung des Pflanzenwachstums Die Erfindung betrifft Mittel zur Beeinflussung des Pflanzenwachstums.Means for influencing plant growth The invention relates to Preparations for influencing plant growth.
Es wurde gefunden, daß Mittel, die als aktiven Bestandteil eine Verbindung der allgemeinen Formel worin R eine substituierte oder unsubstituierte Formyl-, Oxymethyl-, Halogenmethyl- oder Carboxylgruppe oder der Rest eines Esters, eines Amides oder eines Salzes einer Carbonsäure ist, während X für ein Halogenatom steht, eine besondere Wirksamkeit in der Beeinflussung des Pflanzenwachstums aufweisen. Dieser Einfluß der Mittel auf Pflanzen kann, je nach der besonderen Anwendung und der Konzentration der Mittel, von einer sehr starken herbiciden Wirkung zu einer milderen Einwirkung auf das Pflanzenwachstum abgewandelt werden.It has been found that agents which contain a compound of the general formula as an active ingredient wherein R is a substituted or unsubstituted formyl, oxymethyl, halomethyl or carboxyl group or the residue of an ester, an amide or a salt of a carboxylic acid, while X stands for a halogen atom, have a particular effectiveness in influencing plant growth. This influence of the agents on plants can, depending on the particular application and the concentration of the agents, be changed from a very strong herbicidal action to a milder action on plant growth.
Insbesondere werden als aktive Bestandteile der erwähnten Mittel die 2, 3, 5, 6-Tetrahalogenbenzoesäuren angewendet, worunter die 2, 3, 5, 6-Tetrachlorbenzoesäure von der Formel bevorzugt ist.In particular, the 2, 3, 5, 6-tetrahalobenzoic acids are used as active constituents of the agents mentioned, including the 2, 3, 5, 6-tetrachlorobenzoic acid of the formula is preferred.
Es ist bereits bekannt, mehrfach chlorierte Benzoesäuren bzw. Alkylbenzoesäuren sowie die ihnen entsprechenden Aldehyde oder Alkohole und ihre Derivate zur Beeinflussung des Pflanzenwachstums zu verwenden. In den betreffenden Literaturstellen finden sich jedoch nur Angaben über 2fach und 3fach chlorsubstituierte Verbindungen, während andererseits bekannt ist, daß z. B. die 2, 3, 4, 5-Tetrachlorbenzoesäure keinerlei Aktivität in bezug auf die Beeinflussung des Pflanzenwachstums aufweist. Sowohl die letztere Tatsache wie das Fehlen jeglichen Hinweises in der Literatur auf die Anwendung von 4fach halogensubstituierten Benzoesäuren oder den entsprechenden, durch Ersatz der Carboxylgruppe entstehenden Verbindungen lassen die bei Anwendung der erfindungsgemäßen, in bestimmter Konfiguration 4fach chlorierten Verbindungen zu erzielenden Ergebnisse besonders überraschend erscheinen.It is already known that polychlorinated benzoic acids or alkylbenzoic acids and the corresponding aldehydes or alcohols and their derivatives for influencing them of plant growth. Find in the relevant literature references However, there is only information about 2-fold and 3-fold chlorine-substituted compounds, while on the other hand it is known that z. B. the 2, 3, 4, 5-tetrachlorobenzoic acid whatsoever Has activity in relation to influencing plant growth. As well as the latter fact as well as the lack of any reference in the literature to the Use of 4-fold halogen-substituted benzoic acids or the corresponding, Compounds formed by replacement of the carboxyl group leave the upon application of the compounds according to the invention, quadruply chlorinated in a certain configuration The results to be achieved appear particularly surprising.
Daß andere mit der Benzoesäure verwandte Verbindungen, wie die p-Aminobenzoesäure, deren Ester, Salze usw. oder die kernhalogenierten aromatischen Ketosäuren, das Wachstum von Pflanzen beeinflussen, ist ebenfalls bekannt, jedoch ließ sich auch hieraus kein Schluß auf die durch die Erfindung vermittelte Lehre ziehen.That other compounds related to benzoic acid, such as p-aminobenzoic acid, their esters, salts, etc. or the nucleus halogenated aromatic keto acids, the It is also known to influence the growth of plants, but it could also be used do not draw any conclusion from this about the teaching conveyed by the invention.
Gemäß der Erfindung benutzt man die 2, 3, 5, 6-Tetrahalogenbenzoesäuren bzw. die anderen oben gekennzeichneten Verbindungen zur Bereitung von flüssigen Mitteln zur Pflanzenbehandlung, wie Lösungen, Ölen, Emulsionen oder Dispersionen, die gegebenenfalls die verschiedensten Netzmittel, wie Alkylarylsulfonate, sulfonierte aromatische Kohlenwasserstoffe u. dgl., enthalten können. Solche flüssigen Mittel werden derart zubereitet, daß sie durch Versprühen oder Vergießen bzw. Beregnen entweder unmittelbar auf die Pflanzen oder auf den Boden zur Anwendung gebracht werden.According to the invention, the 2, 3, 5, 6-tetrahalobenzoic acids are used or the other compounds identified above for the preparation of liquids Agents for plant treatment, such as solutions, oils, emulsions or dispersions, which optionally sulfonated a wide variety of wetting agents, such as alkylarylsulfonates aromatic hydrocarbons and the like. Such liquid funds are prepared in such a way that they can be sprayed or poured or sprinkled applied either directly to the plants or to the soil will.
Ebenso können die Verbindungen nach der Erfindung auch trocken, d. h. in Form von Stäubemitteln in Verbindung mit den verschiedensten festen feinverteilten aktiven oder inerten Stoffen, wie Füllmitteln, z. B. Diatomeenerde, Talkum, Kreide, Fullererde, Aschenpulver u. dgl., angewandt werden.Likewise, the compounds according to the invention can also be dry, i.e. H. in the form of dusts in connection with the most diverse solid finely divided active or inert substances, such as fillers, e.g. B. diatomaceous earth, talc, chalk, Fuller's earth, ash powder and the like can be used.
Die für den jeweiligen besonderen Anwendungszweck zu benutzende Anteilsmenge der 2, 3, 5, 6-Tetrahalogenverbindung hängt selbstverständlich von der Natur der zu behandelnden Pflanzen, dem Grade der gewünschten Beeinflussung des Pflanzenwachstums bzw. der beabsichtigten Wirkung als Pflanzengift und außerdem von der Einwirkungszeit und den Anwendungsbedingungen, wie Klima, Wetter usw., ab.The proportion to be used for the particular application the 2, 3, 5, 6-tetrahalogen compound depends of course on the nature of the Plants to be treated, the degree of the desired influence on plant growth or the intended effect as a plant poison and also the exposure time and the conditions of use such as climate, weather, etc.
Bei der 2, 3, 5, 6-Tetrachlorbenzoesäure wurde im allgemeinen gefunden, daß ihre Eigenschaften zur Beeinflussung des Pflanzenwachstums bereits in Konzentrationen von nur 0,0001 Gewichtsprozent in Erscheinung treten. Höhere Konzentrationen, -wie 0,001 bis 0,1 Gewichtsprozent, führen zur Vernichtung der Pflanzen. Es folgt daraus, daß, beispielsweise bei der Unkrautbekämpfung, auch die höheren Konzentrationen benutzt, in gewissen Fällen sogar bevorzugt werden. In den meisten, wenn nicht in allen Fällen ist die gewünschte toxische Wirkung für die Konzentration und die Anwendungsform der Mittel maßgebend.In the case of 2, 3, 5, 6-tetrachlorobenzoic acid, it was generally found that their properties for influencing plant growth are already in concentrations of only 0.0001 percent by weight in appearance step. Higher concentrations, -like 0.001 to 0.1 percent by weight, lead to the destruction of the plants. It follows from the fact that, for example in weed control, the higher concentrations used, in certain cases even preferred. In most, if not in In all cases, the desired toxic effect is dependent on the concentration and the form of application the means decisive.
Die 2, 3, 5, 6-Tetrachlorbenzoesäure ist zur vielfachen Anwendung zwecks Beeinflussung des Pflanzenwachstums unter anderem auch als Mittel gegen Pflanzenkrankheiten bzw. -schädlinge geeignet, ihre Hauptanwendung findet sie jedoch als Herbicid, wie aus dem Beispiel hervorgeht. Beispiel Anwendung von 2, 3, 5, 6-Tetrachlorbenzoesäure als Herbicid Auf die Erde rund um 3 Wochen alte Tomatenpflanzen in Tontöpfen werden 10 cm3 wäßrige Lösungen versprüht, in welchen die Säure jeweils in den Konzentrationen 0,1, 0,01, 0,001 und 0,0001 °/o enthalten ist. Die 0,1 a/oige Lösung führte zu starker Verdickung, Verbiegung und Verdrehung des Stammes, der Wuchs war völlig verkümmert. Die 0,01 0/Qige Lösung führte in ähnlicher Weise zum Verbiegen bzw. Abknicken des Stammes und zur Wucherung. Die 0,001%ige Lösung verursachte starke Veränderungen an den Blättern, jedoch keine Verdickung des Stammes, und die 0,0001 %ige Lösung führte nur zu Veränderungen an den Blättern.The 2, 3, 5, 6-tetrachlorobenzoic acid is for multiple applications for the purpose of influencing plant growth, among other things as an agent against plant diseases or pests suitable, but its main application is as a herbicide, such as is evident from the example. Example application of 2, 3, 5, 6-tetrachlorobenzoic acid as a herbicide. On the ground around 3 weeks old tomato plants in clay pots 10 cm3 of aqueous solutions are sprayed, in which the acid in each case in the concentrations 0.1, 0.01, 0.001 and 0.0001% is included. The 0.1 a / o solution led to stronger Thickening, bending and twisting of the trunk, the growth was completely stunted. The 0.01% solution similarly led to bending or kinking of the Tribal and to overgrowth. The 0.001% solution caused major changes on the leaves, but no thickening of the trunk, and the 0.0001% solution only led to changes in the leaves.
Vergleichsversuche mit der unter der Handelsbezeichnung z>2, 4-Da bekannten 2, 4-Dichlorphenoxyessigsäure zeigten, daß die Produkte nach der Erfindung diesem viel verwendeten Herbicid mindestens ebenbürtig, in gewissen Fällen überlegen sind. Insbesondere ist die Selektivität von z. B. 2, 3, 5, 6-Tetrachlorbenzoesäure als Vorzug zu erwähnen. Durch Kontrollversuche wurde nachgewiesen, daß dieses Mittel im Gegensatz zu vielen anderen vorgeschlagenen Herbiciden in einer gegen Unkraut voll wirksamen Dosierung gegenüber Maispflanzen so gut wie unschädlich ist.Comparative tests with the one under the trade name z> 2, 4-Da known 2, 4-dichlorophenoxyacetic acid showed that the products according to the invention At least as good as this much used herbicide, superior in certain cases are. In particular, the selectivity of z. B. 2, 3, 5, 6-tetrachlorobenzoic acid to be mentioned as a preference. Control experiments have shown that this agent unlike many other proposed herbicides in one against weeds fully effective dosage against maize plants is as good as harmless.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1019324XA | 1954-06-04 | 1954-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1019324B true DE1019324B (en) | 1957-11-14 |
Family
ID=22287235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED20595A Pending DE1019324B (en) | 1954-06-04 | 1955-06-03 | Preparations for influencing plant growth |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1019324B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1079885B (en) | 1959-01-29 | 1960-04-14 | Basf Ag | Means for combating unwanted plant growth |
| DE1115516B (en) | 1958-10-15 | 1961-10-19 | Amchem Prod | Herbicides |
| DE1115514B (en) | 1957-11-19 | 1961-10-19 | Amchem Prod | Herbicides |
| DE1133176B (en) | 1957-11-05 | 1962-07-12 | Philips Nv | Preparations for influencing plant growth |
| DE1138278B (en) * | 1958-04-24 | 1962-10-18 | Amchem Prod | Plant killers, especially herbicides |
| DE1146693B (en) | 1958-09-15 | 1963-04-04 | Amchem Prod | Process for converting biennial fruit trees, especially apple trees, into annual fruiting ones |
| DE1267903B (en) * | 1958-12-17 | 1968-05-09 | Du Pont | Total herbicide |
| DE1417429B1 (en) * | 1959-08-04 | 1972-09-14 | Velsicol Chemical Corp | 2-methoxy-3,6-dichlorobenzoic acid, its acid anhydride, salts, esters and amides |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE567705C (en) * | 1928-10-09 | 1933-01-07 | William Eggert Jun | Method of treating seed plants |
| 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 |
-
1955
- 1955-06-03 DE DED20595A patent/DE1019324B/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE567705C (en) * | 1928-10-09 | 1933-01-07 | William Eggert Jun | Method of treating seed plants |
| 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 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1133176B (en) | 1957-11-05 | 1962-07-12 | Philips Nv | Preparations for influencing plant growth |
| DE1115514B (en) | 1957-11-19 | 1961-10-19 | Amchem Prod | Herbicides |
| DE1138278B (en) * | 1958-04-24 | 1962-10-18 | Amchem Prod | Plant killers, especially herbicides |
| DE1146693B (en) | 1958-09-15 | 1963-04-04 | Amchem Prod | Process for converting biennial fruit trees, especially apple trees, into annual fruiting ones |
| DE1115516B (en) | 1958-10-15 | 1961-10-19 | Amchem Prod | Herbicides |
| DE1267903B (en) * | 1958-12-17 | 1968-05-09 | Du Pont | Total herbicide |
| DE1079885B (en) | 1959-01-29 | 1960-04-14 | Basf Ag | Means for combating unwanted plant growth |
| DE1417429B1 (en) * | 1959-08-04 | 1972-09-14 | Velsicol Chemical Corp | 2-methoxy-3,6-dichlorobenzoic acid, its acid anhydride, salts, esters and amides |
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