IE45599B1 - Methods of treating plants and crops with propynlamine derivatives and pesticidal preparations suitable therefor - Google Patents
Methods of treating plants and crops with propynlamine derivatives and pesticidal preparations suitable thereforInfo
- Publication number
- IE45599B1 IE45599B1 IE450/77A IE45077A IE45599B1 IE 45599 B1 IE45599 B1 IE 45599B1 IE 450/77 A IE450/77 A IE 450/77A IE 45077 A IE45077 A IE 45077A IE 45599 B1 IE45599 B1 IE 45599B1
- Authority
- IE
- Ireland
- Prior art keywords
- methyl
- propynyl
- chlorobenzyl
- preparation
- salt
- Prior art date
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations 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
Abstract
The present invention provides pesticidally active compounds of the general formula I (I) in which R represents a group of the formula in which n represents 0, 1, 2 or 3 and each X represents an alkoxy group or a halogen atom; when n represents 2 or 3 the substituents represented by X may be the same or different.
Description
The present invention is concerned with methods of treating plants and crops with pesticidally active, especially insecticidally and ovicidally active, 2-propynylamine derivatives and with pesticidal preparations suitable therefor containing such 2-propynylamine derivatives.
& There have already become known as monoamine oxidase inhibitors, compounds which include for example, trans-2-phenylcyclopropylamine sulphate, l-isonicotinyl-2-isopropyl hydrazine phosphate, isonicotinic acid 2-{2-(benzylcarbamoyl)-ethyl}-hydrazide and also a 2-propynylamine derivative, namely N-benzyl-K-m2thyl-2-propynylamine.
It has now been found that 2-propynylamine derivatives of the general formula I
CH3
R-CHj-N-CH2-C=CH (I), in which R represents an unsubstituted or substituted aromatic hydrocarbon group, and salts thereof, surprisingly exhibit an outstanding action against insect pests as well as against their eggs.
This action is especially.surprising and could not have been foreseen, since the other oxidase inhibitors mentioned above do not have such an action.
The action found is effective in particular, agains Lepidoptera, thus, for example, against Spodoptera littoratis (Egyptian cotton moth),
Namestra brassicae (cabbage moth) and Pieris brassicae (large cabbage butterfly).
Moreover, the compounds of the general formula I and their salts are distinguished by a slight toxicity towards warm-blooded animals.
Thus, for example, the acute LDS0-mouse per os is 700 mg/kg in the case
- 2 45599 of N-benzyl-N-methyl-2-propynylamine, and 305 mg/kg in the case of N(2-chloro-benzyl)-N-methyl-2-propynylami ne.
Furthermore, as these compounds are particularly well tolerated by plants, they can be used advantageously and without danger against pests in vegetable crops.
As such crops there may be mentioned, for example, crops of cotton, tomatoes, cauliflower, cabbage, dwarf beans. Riff beans, sugar beet, maize and rice.
The present invention accordingly provides a pesticidal preparation, which comprises at least one compound selected from compounds of the general formula I
CH,
I
R-—CH^ N CH2—CeCH (I), in which R represents an unsubstituted or substituted aromatic hydrocarbon group, and salts thereof, in admixture or conjunction with a suitable carrier.
The present invention further provides a pesticidal preparation which comprises at least two compounds selected from compounds of the general formula I, in which R has the meaning given above, and salts thereof.
The present invention further provides a method of protecting a living plant against pests, wherein the plant is treated with at least one compound selected from compounds of the general formula I, in which
- 3 R has the meaning given above, and salts thereof.
The present invention further provides a method of protecting a crop against pests, wherein the crop is treated with at least one compound selected from compounds of the general formula I, in v’Ah R h s the meaning given above, and salts thereof.
The most favourable application concentration for the active compounds used in accordance with the methods of the present invention when applied in the form of pesticidal preparations is approximately 0.01% to 1.0%, preferably 0.05% to 0.2%, by weight; when two or more of these active compounds are used these concentration ranges refer of course to the total concentrations.
Among the compounds of the general formula I and their salts there may be used in accordance with the present invention more especially those in which R represents a group of the formula
in which £ represents 0, 1, 2 or 3 and each X represents an alkyl, alkoxy or nitro group or a halogen atom; when n, represents 2 or 3 the substituents represented by X may be the same or different.
However, optimum actions occur in the case of those compounds in 20 which according to the general formula I, £ represents 0, 1, 2 or 3 and X represents an alkyl or alkoxy group containing 1 to 3 carbon atoms, a chlorine atom or a nitro group.
- 4 45599
The compounds of the general formula I used in accordance with the present invention may be applied in each case, in the free form or in the form of salts thereof with inorganic or organic acids.
Among the salts, the hydrochlorides are especially suitable for 5 use in accordance with the present invention.
Specific compounds and salts which may be used in accordance with the present invention are, for example, those listed in the following Table:
TABLE I
Compound Physical Constant N-(4-Chlorobenzyl)-N-methyl-2-propynylamine B.P.:96-106°C/2 torr 4-Chlorobenzyl-methyl-2-propynyl-ammoniurn chloride M.p.: 216.5-217°C N-Benzyl-N-methyl-2-propynylami ne B.p.: 115-120°C/25 torr N-(2-Chlorobenzyl)-N-methyl-2-propynylami ne B.p.: 92-94°C/2.5 torr N-(3-Chlorobenzyl)-N-methyl-2-propynylami ne B.p.: 94-103°C/3 torr N-(3,4-Di chiorobenzyl)-N-methyl-2-propynylami ne n§° = 1.5497 N-(2,4-Di chiorobenzyl)-N-methyl-1-2-propynylami ne ng° = 1.5485 N-(-3-Methoxybenzyl)-N-methyl-2-propynylami ne B.p.: 102-105°C/l torr Benzyl-methyl-2-propynyl-ammoniurn chioride M.p.: 154-155°C 2-Chlorobenzyl-methyl-2-propynyl-ammoni urn chloride M.p.: 160-160.5°C 3-Chlorobenzyl-methyl-2-propynyl-ammoni urn chloride M.p.: 182-183.5°C 2,4-Di ch1orobenzyl-methyl-2-propynyl-ammonium chloride M.p.: 171-172°C
- 5 45599
TABLE I (Continued)
Compound_Physical Constant
3-Methoxybenzy1-methyl-2-propynylammonium chloride M.p.: 165-166°C
3,4-Di chlorobenzyl-methyl-2-propynylammonium chloride M.p.: 185-186°C
The free bases are colourless liquids that are readily soluble in organic solvents, for exiample hydrocarbons, halogenated hydrocarbons, ethers, ketones, alcohols, esters, carboxylic acid amides and carboxylic acid nitriles. Their solubility in water is slight. The 2-propynylamine derivatives can be isolated easily as crystalline bodies in the form of their hydrogen halide salts; the latter are readily soluble in water, but only sparingly soluble in organic solvents.
The compounds used in accordance with the present invention are known per se or may be prepared by processess known per se.
They may be prepared, for example, by reacting a propargyl halide of the general formula
HC=C—CH2—Hal, in which Hal represents a halogen atom, preferably a chlorine or bromine atom, in the presence of a solvent and of an acid-binding agent with an N-substituted methylamine of the general formula
R—CHj—NH—CH3, in which R has the meaning given above, and, if desired, converting the resulting compound of the general formula I into a salt thereof with
- 6 45399 an acid.
In order to synthesize the compounds of the general formula I, the reactants are used in approximately equimolar quantities. Suitable reaction media are solvents that are inert towards the reactants. The following are mentioned as examples of such solvents: halogenated hydrocarbons, for example methylene chloride, chloroform and carbon tetrachloride, aliphatic and aromatic hydrocarbons, for example petroleum ether, cyclohexane, benzene, toluene and xylene, alcohols for example methanol and ethanol, and ketones, for example acetone, methyl isobutyl ketone and isophorone.
The reaction takes place between 0° and 100°C, but generally between room temperature and the reflux temperature of the reaction mixture in question.
Tertiary amines, for example triethylamine or Ν,Ν-dimethylaniline, pyridine bases or suitable inorganic bases, for example oxides, hydroxides and carbonates of alkali metals and alkaline earth metals, are used to bind the hydrohalic acids formed.
As a rule, the propargyl halide is added portionwise to the appropriate N-substituted methylamine and the hydrogen halide acceptor, but it is also possible to add the reactants in the reverse order.
After the reaction has taken place, the hydrogen halide salt formed is removed by filtration and washed with the appropriate solvent. After removing the solvent from the filtrate, the residue is subjected to fractional distillation under reduced pressure and the reaction products are obtained as colourless liquids.
The salts of the 2-propynylamine derivatives may, if desired, be
- 7 Ρ 45599 obtained by treating the amines with, for example, ethereal solutions of the acids while cooling.
They can be easily recrystallized from a suitable organic solvent, for example a mixture of ethanol and ether.
The active compounds used in accordance with the present invention may be applied alone, or in the form of mixtures with one another or with other active substances. If desired, other plant-protecting agents or pest-combating agents may be added depending on the purpose desired.
The action and speed of action can be enhanced, for example, by action-increasing additives, for example organic solvents, wetting agents and oils) This permits a reduction in the quantity of the active substance itself applied.
The active compounds used in accordance with the present invention or mixtures thereof are advantageously applied in the form of pesticidal preparations, for example powders, strewable preparations, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid vehicles or diluents and, if desired, of surface-active agents, for example wetting, adherent, emulsifying and/or dispersing agents.
Suitable liquid carriers are, for example, water, aliphatic hydrocarbons, aromatic hydrocarbons, for example benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide and dimethylformamide, and also mineral oil fractions.
Suitable solid carriers are, for example, mineral earths, for example Tonsil (Trade Mark), silica gel, talcum, kaolin, attaclay, limestone and silicic acid, and vegetable products, for example meals.
- 8 45599
As surface-active agents there may be mentioned, for example, calcium lignin sulphonate, polyoxyethylene alkyl phenyl ethers, naphthalene sulphonic acids and salts thereof, phenol sulphonic acids and salts thereof, formaldehyde condensates, fatty alcohol sulphates and also substituted benzene sulphonic acids and salts thereof.
The total amount of the active substance or substances in the various pesticidal preparations may vary within wide limits. For example, concentrate preparations ready for dilution before application may contain approximately 10 to 80% by weight of active substance(s), approximately 90 to 20% by weight of liquid or solid carrier and, if desired, also up to 20% by weight of surface-active agent(s).
The active compounds may be applied in the usual manner, for example with water as carrier in quantities of spray liquor of about 100 to 1000 litres per hectare. It is also possible to apply the active compounds by the so-called low-volume and ultra-low-volume methods as well as in the form of so-called microgranules.
The production of these preparations may be carried out in a manner known per se, for example by mixing or grinding methods. If desired, the individual components may be mixed together only shortly before they are used, as is the case in practice, for example, in the so-called tank-mix method.
The following Examples illustrate the invention. Examples 1 and 2 illustrate the manufacture of the compounds of the general formula I and their salts, and Examples 3 to 5 illustrate their pesticidal action.
- 9 455.89
Example 1.
N-(4-Chlorobenzyl)-N-methyl-2-propynylamine.
23.8 Grams (0.2 mole) of propargyl bromide were added portionwise at room temperature, while stirring, to a solution of 31.1 grams (0.2 mole) of N-(4-chlorobenzyl)-methylamine and 30.3 grams (0.3 mole) of triethylamine in 150 ml of dry benzene. The solution was heated for 17 hours under reflux. The mixture was then filtered to remove the solid phase, the solvent was distilled off in vacuo, and the residue remaining was subjected to fractional distillation under reduced pressure 30.9 Grams of N-(4-chlorobenzyl)-N-methyl-2-propyny1amine (79% of the theoretical yield) were thus obtained as a colourless liquid having a boiling point Of 96—1O6°C/2 torr.
Example 2.
4-Chlorobenzyl-methyl-2-propynyl-ammonium chloride.
ml of an HCl-saturated ether solution were added at -5°C to a solution of 5 grams (0.0258 mole) of N-(4-chlorobenzyl)-N-methyl-2propynylamine in 50 ml of ether. It was allowed to stand overnight at room temperature, and then the thick, white crystalline magma was removed
- 10 4SS98 by filtering with suction, washed with ether, and recrystallized from an ethanol-ether mixture. 5.6 Grams (94.5% of the theoretical yield) of 4-chlorobenzyl-methyl-2-propynyl-ammonium chloride having a melting point of 216.5—217°C were obtained.
Each of the other compounds listed in Table I above can be prepared in a manner analogous to that described in Example(s) 1 and/or 2.
Example 3.
In a series of tests the compounds used in accordance with the present invention were applied as aqueous solutions of the salts or as aqueous emulsions of the bases, which had been formulated as emulsion concentrates, the application being carried out in each case at the concentration indicated in the Table below. The procedure was the same with two of the three agents used for comparison, namely trans-2-phenylcyclopropylamine sulphate and l-isonicotinyl-2-isopropylhydrazine phosphate; in the case of the other agent used for comparison, namely isonicotinic acid 2-{2-(benzylcarbamoyl)-ethyl}-hydrazide, the compound was dissolved in acetone and diluted with water to the concentration indicated in the Table.
Batches of eggs, 2 to 3 days old, of the Egyptian cotton moth, which had been deposited on filter paper by fertilized female moths, were immersed in the aforesaid preparations of active substances until complete wetting was achieved and then placed in closed Petri dishes until they were assessed 4 days after the treatment.
The criterion for evaluating the pesticidal action was the percentage emergence prevention as compared with untreated eggs.
The results obtained are summarized in the following Table,
- 11 4559®
Active substance Emergence prevention as % Compound in accordance with the invention concentration (%) N-(4-Chlorobenzyl)-N-methyl-2-propynylamine 0.02 100 5 4-Chlorobenzyl -methyl -2-propynyl -ammoni urn chloride 0.1 100 N-Benzyl-N-methyl-2-propynylami ne 0.04 100 N-(2-Chlorobenzyl)-N-methyl-2-propynylami ne 0.1 100 N-(3-Chlorobenzyl)-N-methyl-2-propynylami ne 0.1 100 10 N-(3,4-Dichlorobenzyl)-N-methyl-2-propynylamine 0.04 100 N- (2,4-Di chiorobenzyl)-N-methyl-2-propynylami ne 0.04 100 N-(3-Methoxybenzyl)-N-methyl-2-propynylami ne 0.1 100 Benzyl-methyl-2-propynyl-ammoni urn chiori de 0.1 100 2-Chlorobenzyl-methyl-2-propynyl-ammoni urn 15 chloride 0.04 80 3-Chlorobenzyl-methyl-2-propynyl-ammoni urn chloride 0.1 100 2 9 4-D ichiorobenzyl-methyl-2-propynyl-ammoni urn chloride 0.1 100 20 3-Methoxybenzyl-methyl-2-propynyl-ammoni urn chloride 0.04 70 3,4-Di chiorobenzyl-methyl-2-propylyl-ammonium 0.04 100 Comparison Agents Trans-2-phenylcyclopropylami ne sulphate 1.0 0 25 l-Isonicotinyl-2-isopropylhydrazine phosphate 1.0 0 isonicotinic acid 2-{2-(benzylcarbamoyl)- ethyll-hydrazide 1.0 0
- 12 455SS
Example 4.
In a series of tests the compounds used in accordance with the present invention were applied as aqueous solutions of the salts or as aqueous emulsions of the bases, which had been formulated as emulsion concentrates, the application being carried out in each case at the concentration indicated in the Table below. The procedure was the same with two of the three agents used for comparison, namely trans-2-phenylcyclopropylamine sulphate and 1-isonicotinyl-2-isopropylhydrazine phosphate; in the case of the other agent used for comparison, namely isonicotinic acid 2-{2-(benzyl carbamoyl)-ethyl}-hydrazide, the compound was dissolved in acetone and diluted with water to the concentration indicated in the Table.
Batches of eggs, two days old, of the large cabbage butterfly, which had been deposited by fertilized female butterflies on cauliflower leaves, were immersed in the aforesaid preparations of active substances until complete wetting was achieved and placed in closed Petri dishes until they were assessed 4 days after the treatment.
The criterion for evaluating the pesticidal action was the percentage emergence prevention as compared with untreated eggs.
The results obtained are summarized in the following Table.
- 13 45599
Active substance Compound in accordance with the concentration Emergence prevention as % present invention (%) N-(4-Chlorobenzyl)-N-methyl-2-propynylamine 0.06 100 5 N-Benzyl-N-methyl-2-propynylami ne 0.1 100 N-(2,4-Di chlorobenzyl)-N-methyl-2- propynylamine 0.1 100 2-Chlorobenzyl-methyl-2-propynyl- ammonium chloride 0.1 100 10 3,4-Di chiorobenzyl-methyl-2-propynyl- ammonium chloride 0.08 100 Comparison Agents Trans-2-phenylcyclopropylami ne sulphate 1.0 0 1-Isoni coti nyl-2-i sopropylhydrazine phosphate 1.0 0 15 Isonicotinic acid 2-{2-(benzylcarbamoyl)- ethyl} hydrazide 1.0 0
Example 5.
In a series of tests the compounds used in accordance with the 20 present invention were applied as an aqueous solution of the salt or as aqueous emulsions of the bases, which had been formulated as emulsion concentrates, the application being carried out at the concentration indicated in the Table below. The procedure was the same with the agents used for comparison, namely trans-2-phenylcyclopropylamine sul25 phate and 1-isonicotinyl-2-isopropylhydrazine phosphate.
Potted mustard seedlings, which had been covered with eggs by female diamond back moths (Plutella maculipennis), were sprayed, until dripping
- 14 45599 wet, with the aforesaid preparations of active substances. After the ' ‘ treatment, the pots were placed in ventilated glass cylinders for 7 days.
The criterion for evaluating the pesticidal action was the damage on the treated plants caused by eating as compared with such damage on untreated plants.
The results obtained are summarized in the following Table.
Active substance Eating Compound in accordance with the concentration damage present invention (%) as %
N-(4-Chlorobenzyl)-N-methyl-2-propynylami ne 0.05 0 N-Benzy1-N-methyl-2-propynylami ne 0.05 0 3,4-Di chlorobenzyl-methyl-2-propynyl- ammonium chloride 0,05 0 Comparison Agents 15 Trans-2-phenylcyclopropylamine sulphate 0.1 100 1-1soni coti nyl-2-i sopropy!hydrazi ne phosphate 0.1 100
- 15 . 4.5599
Claims (20)
1. WHAT WE CLAIM IS;1. A pesticidal preparation which comprises at least one compound selected from compounds of the general formula I R—CHg·· Ν CH^—C ξ CH (I). 2. ,4-di chlorobenzyl-methyl-2-propynyl-ammoni urn chiori de, 3-methoxybenzyl-methyl-2-propynyl-ammonium chloride and 2- chlorobenzyl-methyl-2-propynyl-ammonium chioride, 2.4- di chlorobenzyl-methyl-2-propynyl-ammoni um chiori de, 2- chlorobenzyl-methyl-2-propynyl-ammoni urn chiori de, 2- chlorobenzyl-methyl-2-propynyl-ammonium chioride, 2,4-diehlorobenzyl-methyl-2-propynyl-ammoni um chiori de, 3-methoxybenzyl-methyl-2-propynyr-ammonium chloride and 2- chlorobenzyl-methyl-2-propynyl-ammoni urn chiori de,
2. A preparation as claimed in claim 1, wherein R represents a group of the formula Xi in which £ represents 0, 1, 2 or 3 and each X represents an alkyl, alkoxy or nitro group or a halogen atom. 3. - chlorobenzyl-methyl-2-propynyl-ammoni urn chiori de, 3.4- di chlorobenzyl-methyl-2-propynyl-ammoni um chiori de. 30. A method as claimed in claim 23, wherein the plant is treated with a pesticidal preparation as claimed in any one of claims 1 to 22. 31. A method as claimed in any one of claims 23 to 29, wherein the plant is treated with a preparation containing the active substance in a concentration of approximately 0.01 to 1.0£ by weight. 32. A method as claimed in claim 31, wherein the concentration is 0.05 to 0.22> by weight. 33. A method as claimed in claim 23, conducted substantially as described in Example 5 herein. 34. A method of protecting a crop against pests, wherein the crop is treated with at least one compound selected from compounds of the general formula I ch 3 I R—CH 2 —N-CH 2 —CsCH (I), in which R represents an unsubstituted or substituted aromatic hydrocarbon 21 group, and salts thereof. 35. A method as claimed in claim 34, wherein R represents a group of the formula 3-methoxybenzyl-methyl-2-propyny1-ammonium chloride and 3- chlorobenzyl-methyl-2-propynyl-ammoni um chiori de, 3,4-di chiorobenzyl-methyl-2-propynyl-ammonium chlori de. 3-methoxybenzyl-methyl-2-propynyl-ammonium chloride and 3- chlorobenzyl-methyl-2-propynyl-ammonium chloride, 25 2,4-dichiorobenzyl-methyl-2-propynyl-anmonium chloride, 3- chlorobenzyl-methyl-2-propynyl-ammoni urn chlori de
3. A preparation as claimed in claim 2, wherein X represents an alkyl or alkoxy group containing 1 to 3 carbon atoms, a chlorine atom or 4. -chlorobenzyl-methyl-2-propynyl-ammonium chloride, 20 N-benzyl-N-methyl-2-propynylami ne, N-(Z-ch1orobenzyl)-N-methyl-2-propynylamine - 22 45539 N-(3-chlorobenzyl)-N-methyl-2-propynylami ne, N-(3,4-di chiorobenzyl)-N-methyl-2-propynylami ne, N-(2,4-di chlorobenzyl)-N-methyl-2-propynylami ne, N-(3-methoxybenzyl)-N-methyl-2-propyny1 amine, 4-chlorobenzyl-methyl-2-propynyl-ammonium chiori de, N-benzyl-N-methyl-2-propynylami ne, - 20 4539s Ν-(2-chlorobenzyl)-N-methyl-2-propynylami ne, N-(3-chlorobenzyl)-N-methyl-2-propynylami ne, N-(3,4-di chiorobenzyl)-N-methyl-2-propynylamine, N- (2,4-di chlorobenzyl)-N-methyl-2-propynylami ne, N-(3-methoxybenzyl)-N-methyl-2-propynylamine, benzyl-methyl-2-propynyl-ammoni urn chiori de, 4-ch1orobenzyl-methyl-2-propynyl-ammonium chloride, N-benzyl-N-methyl-2-propynylami ne,
4. A preparation as claimed in any one of claims 1 to 3, wherein each salt is a salt with an inorganic acid. 5. Benzyl-methyl-2-propynyl-ammonium chloride, 5 in which £ represents 0, 1, 2 or 3 and each X represents an alkyl, alkoxy or nitro group or a halogen atom. 35. A method as claimed in claim 35, wherein X represents an alkyl or alkoxy group containing 1 to 3 carbon atoms, a chlorine atom or a nitro group. 5 or a nitro group, 5 N-(2-chlorobenzyl)-N-methyl-2-propynylami ne, N-(3-chlorobenzyl)-N-methyl-2-propynylami ne, N-(3,4-di chiorobenzyl)-N-methyl-2-propynylami ne, N-(2,4-dichlorobenzyl)-N-methyl-2-propynylamine, N-(3-methoxybenzyl)-N-methyl-2-propynylami ne,
5. A preparation as claimed in claim 4, wherein each salt is a hydrochloride. 20 5 in which R represents an unsubstituted or substituted aromatic hydrocarbon group, and. salts thereof, in admixture or conjunction with a suitable carrier.
6. A preparation as claimed in any one of claims 1 to 3, wherein each salt is a salt with an organic acid.
7. A preparation as claimed in any one of claims 1 to 5, containing
8. A pesticidal preparation, comprising at least two compounds selected from compounds of the general formula ϊ CH, I r_CH 2 —N—CH 2 —C=CH (I), in which R represents an unsubstituted or substituted aromatic hydro20 carbon group, and salts thereof.
9. A preparation as claimed in claim 8, wherein R represents a group of the formula 10. 3,4-dichiorobenzyl-methyl-2-propynyl-ammonium chloride. 41. A method as claimed in claim 34, wherein the crop is treated With a pesticidal preparation as claimed in any one of claims 1 to 22, 42. A method as claimed in any one of claims 34 to 40, wherein the crop is treated with a preparation containing the active substance in 10 37. A method as claimed in any one of claims 34 to 36, wherein each salt is a salt with an inorganic acid. 38. A method as claimed in claim 37, wherein each salt is a hydrochloride. 39. A method as claimed in any one of claims 34 to 36, wherein each 15 salt is a salt with an organic acid. 40. A method as claimed in any one of claims 34 to 38, wherein the crop is treated with at least one compound selected from N-(4-ch1orobenzyl)-N-methyl-2-propynylamine, 10 or alkoxy group containing 1 to 3 carbon atoms, a chlorine atom or a nitro group. 26. A method as claimed in any one of claims 23 to 25, wherein each salt is a salt with an inorganic acid. 27. A method as claimed in claim 26, wherein each salt is a hydro15 chloride. 28. A method as claimed in any one of claims 23 to 25, wherein each salt is a salt with an organic acid. 29. A method as claimed in any one of claims 23 to 27, wherein the plant is treated with at least one compound selected from 20 N-(4-chlorobenzyl)-N-methyl-2-propynylamine,
10. A preparation as claimed in claim 9, wherein X represents an alkyl or alkoxy group containing 1 to 3 carbon atoms, a chlorine atom 10 benzyl-methyl-2-propynyl-ammoniurn chloride,
11. A preparation as claimed in any one of claims 8 to 10, wherein each salt is a salt with an inorganic acid.
12. A preparation as claimed in claim 11, wherein each salt is a hydrochloride. 10
13. A preparation as claimed in any one of claims 8 to 10, wherein each salt is a salt with an organic acid.
14. A preparation as claimed in any one of claims 8 to 12, contain ing at least two compounds selected from N-(4-chlorobenzy1)-N-methyl-2-propynylamine, 15. A concentration of approximately 0.01 to 1,0$ by weight. 43. A method as claimed in claim 42, wherein the concentration is 0.05 to 0.2% by weight. 44. A method as claimed in any one of claims 34 to 43, wherein the crop is a cotton, tomato, cauliflower, cabbage, dwarf bean, Riff bean,
15. A preparation as claimed in any one of claims 1 to 14, which is in the fora of a powder, a strewable preparation, granules, a solution, an emulsion or a suspension. 15 4-chloroberizyl-methyl-2-propynyl-ammonium chloride, N-benzyl-N-methyl-2-propynylanrine, N-(2-chlorobenzyl)-N-methyl-2-propynylami ne, N-(3-chiorobenzyl)-N-methyl-2-propynylami ne, N-(3,4-di chlorobenzyl)-N-methyl-2-propynylamine, 20 N-(2,4-di chlorobenzyl)-N-methyl-2-propynylami ne, N-(3-methoxybenzyl)-N-methyl-2-propynylamine, benzyl-methyl-2-propynyl-ammonium chloride, 15 3,4-dich1orobenzy1-methyl-2-propynyl-ammonium chloride. 15 a nitro group.
16. A preparation as claimed in any one of claims 1 to 7 and 15, containing a single compound selected from compounds of the general formula I and salts thereof. - 16 45599 at least one compound selected from N-(4-chlorobenzyl)-N-methyl-2-propynylamine,
17. A preparation as claimed in any one of claims 1 to 7 and 15, containing two or more compounds selected from compounds of the general formula I and salts thereof. - 17 45599 in which £ represents 0, 1, 2 or 3 and each X represents an alkyl, alkoxy or nitro group or a halogen atom.
18. A preparation as claimed in any one of claims 1 to 17, which also contains one or more active substances selected from plant-protecting agents and pest-combating agents other than compounds of the general formula I and salts thereof. - 18 4559
19. A preparation as claimed in any one of claims 1 to 18, wherein the total amount present of active substance or substances is approximately 10 to 80% by weight. 20. A preparation as claimed in any one of claims 1 to 19, containing a single surface-active agent in an amount of up to 20% by weight. 21. A preparation as claimed in any one of claims 1 to 19, containing two or more surface-active agents in a total amount of up to 20% by weight. 22. Any one of the pesticidal preparations as claimed in claim 1 and substantially as described in any one of Examples 3 to 5 herein. 23. A method of protecting a living plant against pests, wherein the plant is treated with at least one compound selected from compounds of the general formula I CH, I R—CH^—N—CH2——CSCH (I), in which R represents an unsubstituted or substituted aromatic hydrocarbon group, and salts thereof. 24. A method as claimed in claim 23, wherein R represents a group 5 of the formula in which ji represents 0, 1, 2 or 3 and each X represents an alkyl, alkoxy or nitro group or a halogen atom. 25. A method as claimed in claim 24, wherein X represents an alkyl
20. Sugar beet, maize or rice crop.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762609280 DE2609280A1 (en) | 1976-03-04 | 1976-03-04 | SCHAEDLING INHIBITOR |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE45599L IE45599L (en) | 1977-09-04 |
| IE45599B1 true IE45599B1 (en) | 1982-10-06 |
Family
ID=5971660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE450/77A IE45599B1 (en) | 1976-03-04 | 1977-03-02 | Methods of treating plants and crops with propynlamine derivatives and pesticidal preparations suitable therefor |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS52108022A (en) |
| AU (1) | AU508246B2 (en) |
| BE (1) | BE852088A (en) |
| CA (1) | CA1090250A (en) |
| CS (1) | CS193084B2 (en) |
| DD (1) | DD129611A5 (en) |
| DE (1) | DE2609280A1 (en) |
| DK (1) | DK50977A (en) |
| FR (1) | FR2342661A1 (en) |
| GB (1) | GB1578852A (en) |
| HU (1) | HU177907B (en) |
| IE (1) | IE45599B1 (en) |
| IL (1) | IL51463A (en) |
| IT (1) | IT1143638B (en) |
| LU (1) | LU76644A1 (en) |
| NL (1) | NL7701575A (en) |
| SU (1) | SU656462A3 (en) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5030625A (en) * | 1984-11-22 | 1991-07-09 | Sandoz Ltd. | Anti-fungal homopropargylamine compounds |
| EP0191269B1 (en) * | 1984-11-22 | 1991-03-06 | Sandoz Ag | Novel homopropargylamines |
| US4933413A (en) * | 1989-04-10 | 1990-06-12 | Dow Corning Corporation | Process for synthesis of acylamino organosilicon compounds |
| ES2354993T3 (en) | 2007-09-07 | 2011-03-21 | Cutech S.R.L. | COMPOSITIONS THAT INCLUDE PARGILINA. |
| US9113347B2 (en) | 2012-12-05 | 2015-08-18 | At&T Intellectual Property I, Lp | Backhaul link for distributed antenna system |
| US9768833B2 (en) | 2014-09-15 | 2017-09-19 | At&T Intellectual Property I, L.P. | Method and apparatus for sensing a condition in a transmission medium of electromagnetic waves |
| US9762289B2 (en) | 2014-10-14 | 2017-09-12 | At&T Intellectual Property I, L.P. | Method and apparatus for transmitting or receiving signals in a transportation system |
| US9769020B2 (en) | 2014-10-21 | 2017-09-19 | At&T Intellectual Property I, L.P. | Method and apparatus for responding to events affecting communications in a communication network |
| US9312919B1 (en) | 2014-10-21 | 2016-04-12 | At&T Intellectual Property I, Lp | Transmission device with impairment compensation and methods for use therewith |
| US9780834B2 (en) | 2014-10-21 | 2017-10-03 | At&T Intellectual Property I, L.P. | Method and apparatus for transmitting electromagnetic waves |
| US9742462B2 (en) | 2014-12-04 | 2017-08-22 | At&T Intellectual Property I, L.P. | Transmission medium and communication interfaces and methods for use therewith |
| US9680670B2 (en) | 2014-11-20 | 2017-06-13 | At&T Intellectual Property I, L.P. | Transmission device with channel equalization and control and methods for use therewith |
| US9544006B2 (en) | 2014-11-20 | 2017-01-10 | At&T Intellectual Property I, L.P. | Transmission device with mode division multiplexing and methods for use therewith |
| US10650940B2 (en) | 2015-05-15 | 2020-05-12 | At&T Intellectual Property I, L.P. | Transmission medium having a conductive material and methods for use therewith |
| US10812174B2 (en) | 2015-06-03 | 2020-10-20 | At&T Intellectual Property I, L.P. | Client node device and methods for use therewith |
| US9509415B1 (en) | 2015-06-25 | 2016-11-29 | At&T Intellectual Property I, L.P. | Methods and apparatus for inducing a fundamental wave mode on a transmission medium |
| US9722318B2 (en) | 2015-07-14 | 2017-08-01 | At&T Intellectual Property I, L.P. | Method and apparatus for coupling an antenna to a device |
| US10784670B2 (en) | 2015-07-23 | 2020-09-22 | At&T Intellectual Property I, L.P. | Antenna support for aligning an antenna |
| US9735833B2 (en) | 2015-07-31 | 2017-08-15 | At&T Intellectual Property I, L.P. | Method and apparatus for communications management in a neighborhood network |
| US9769128B2 (en) | 2015-09-28 | 2017-09-19 | At&T Intellectual Property I, L.P. | Method and apparatus for encryption of communications over a network |
| US9729197B2 (en) | 2015-10-01 | 2017-08-08 | At&T Intellectual Property I, L.P. | Method and apparatus for communicating network management traffic over a network |
| US10665942B2 (en) | 2015-10-16 | 2020-05-26 | At&T Intellectual Property I, L.P. | Method and apparatus for adjusting wireless communications |
| US11032819B2 (en) | 2016-09-15 | 2021-06-08 | At&T Intellectual Property I, L.P. | Method and apparatus for use with a radio distributed antenna system having a control channel reference signal |
| US10811767B2 (en) | 2016-10-21 | 2020-10-20 | At&T Intellectual Property I, L.P. | System and dielectric antenna with convex dielectric radome |
| US10727599B2 (en) | 2016-12-06 | 2020-07-28 | At&T Intellectual Property I, L.P. | Launcher with slot antenna and methods for use therewith |
| US10637149B2 (en) | 2016-12-06 | 2020-04-28 | At&T Intellectual Property I, L.P. | Injection molded dielectric antenna and methods for use therewith |
| US10755542B2 (en) | 2016-12-06 | 2020-08-25 | At&T Intellectual Property I, L.P. | Method and apparatus for surveillance via guided wave communication |
| US10819035B2 (en) | 2016-12-06 | 2020-10-27 | At&T Intellectual Property I, L.P. | Launcher with helical antenna and methods for use therewith |
| US10694379B2 (en) | 2016-12-06 | 2020-06-23 | At&T Intellectual Property I, L.P. | Waveguide system with device-based authentication and methods for use therewith |
| US10601494B2 (en) | 2016-12-08 | 2020-03-24 | At&T Intellectual Property I, L.P. | Dual-band communication device and method for use therewith |
| US10938108B2 (en) | 2016-12-08 | 2021-03-02 | At&T Intellectual Property I, L.P. | Frequency selective multi-feed dielectric antenna system and methods for use therewith |
| US10777873B2 (en) | 2016-12-08 | 2020-09-15 | At&T Intellectual Property I, L.P. | Method and apparatus for mounting network devices |
| US10916969B2 (en) | 2016-12-08 | 2021-02-09 | At&T Intellectual Property I, L.P. | Method and apparatus for providing power using an inductive coupling |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB918217A (en) * | 1900-01-01 | |||
| BE591650A (en) * | 1959-06-10 | 1960-10-03 | Abbott Lab | Method for inhibiting the action of mono-amine oxidase in warm-blooded animals |
| US3149160A (en) * | 1961-03-23 | 1964-09-15 | Dow Chemical Co | Nu-(2-propynyl) omiron-bromoaniline |
| US3121745A (en) * | 1961-03-23 | 1964-02-18 | Dow Chemical Co | Propynly p-nitroanilines |
| US3231614A (en) * | 1963-12-26 | 1966-01-25 | Dow Chemical Co | N-2-propynyl and n, n-di(2-propynyl)-(2-propynyloxy)-anilines |
| US3781443A (en) * | 1971-10-26 | 1973-12-25 | Lilly Co Eli | Phenethanolamine n-methyl transferase inhibiting benzylamines |
-
1976
- 1976-03-04 DE DE19762609280 patent/DE2609280A1/en not_active Withdrawn
-
1977
- 1977-01-26 LU LU76644A patent/LU76644A1/xx unknown
- 1977-02-04 CS CS77749A patent/CS193084B2/en unknown
- 1977-02-08 DK DK50977A patent/DK50977A/en not_active Application Discontinuation
- 1977-02-10 CA CA271,480A patent/CA1090250A/en not_active Expired
- 1977-02-15 NL NL7701575A patent/NL7701575A/en not_active Application Discontinuation
- 1977-02-16 IL IL51463A patent/IL51463A/en unknown
- 1977-02-21 GB GB7195/77A patent/GB1578852A/en not_active Expired
- 1977-03-02 IE IE450/77A patent/IE45599B1/en unknown
- 1977-03-03 AU AU22897/77A patent/AU508246B2/en not_active Expired
- 1977-03-03 HU HU77SCHE596A patent/HU177907B/en unknown
- 1977-03-03 SU SU772456551A patent/SU656462A3/en active
- 1977-03-04 BE BE175468A patent/BE852088A/en not_active IP Right Cessation
- 1977-03-04 JP JP2370277A patent/JPS52108022A/en active Granted
- 1977-03-04 IT IT20932/77A patent/IT1143638B/en active
- 1977-03-04 DD DD7700197682A patent/DD129611A5/en unknown
- 1977-03-04 FR FR7706455A patent/FR2342661A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52108022A (en) | 1977-09-10 |
| IT1143638B (en) | 1986-10-22 |
| IE45599L (en) | 1977-09-04 |
| FR2342661A1 (en) | 1977-09-30 |
| AU2289777A (en) | 1978-09-07 |
| JPS574601B2 (en) | 1982-01-27 |
| CA1090250A (en) | 1980-11-25 |
| SU656462A3 (en) | 1979-04-05 |
| NL7701575A (en) | 1977-09-06 |
| IL51463A0 (en) | 1977-04-29 |
| HU177907B (en) | 1982-01-28 |
| DK50977A (en) | 1977-09-05 |
| FR2342661B1 (en) | 1980-06-27 |
| DD129611A5 (en) | 1978-02-01 |
| BE852088A (en) | 1977-09-05 |
| LU76644A1 (en) | 1977-06-24 |
| DE2609280A1 (en) | 1977-09-15 |
| CS193084B2 (en) | 1979-09-17 |
| GB1578852A (en) | 1980-11-12 |
| AU508246B2 (en) | 1980-03-13 |
| IL51463A (en) | 1980-11-30 |
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