CA1129882A - Benzamide derivatives and their use as herbicides - Google Patents
Benzamide derivatives and their use as herbicidesInfo
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- CA1129882A CA1129882A CA353,781A CA353781A CA1129882A CA 1129882 A CA1129882 A CA 1129882A CA 353781 A CA353781 A CA 353781A CA 1129882 A CA1129882 A CA 1129882A
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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
- 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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE The present invention relates to new substituted benzamides of the formula wherein R represents a vinyl or ethinyl radical. The inven-tion also relates to the use of such compounds as herbicides per se, or in combination with other pesticidal or herbicidal substances. Preferably, they are used in the form of liquid or solid mixtures, or liquid or solid solutions. The invention also relates to a process of making the herbicides.
Description
Z~882 The present invention rela-tes to new substituted benzamides oE the formula O-C-NI-I-CH -R
CH3~CH3 wherein R represents a vinyl or ethinyl radical. The inven-tion also relates to the use of such compounds as herbicides per se, or in combination with other pesticidal or herbicidal substances. Preferably, they are used in the ~orm of liquid or solid mixtures, or liquid or solid solutions.
A number of substances of the benzam:ide series are already known which have herbicidal properties. U.S. patents 3,534,098 and 3,640,699 describe 3,5-disubstituted 1,1-dimethylpropinyl henzamides and their use as herbicides. As substituents in the 3,5 positions, F,Cl,Br or the methyl radical are mentioned. U.S. patent 3,551,484 describes N-(l,l-dimethyl-propenyl) -3,5-disubstituted benzamide 5 and their herbicidal properties.
From this series, the 3,5-dichloro-N-(l,l-dimethyl~
propinyl)-benzamide, which is sold commercially under the trademark "KERB", has achie~ed particular importance; this compound has, however, in its phytotoxic activity, the drawback of low tolerance to a number of useful plants.
In J. Agr. Food Chem., Vol. 19, No. 3, 1971, p. 417-21, the relationships between structure and herbiciclal ~., 9~3~Z
activity are studied on a number of benzamides, which have a similar skructure to 3,5-dichloro-N-(1,1-dlmethylpropinyl)-benzamide. In this article it is shown that di-substikution at the aromatic radical leads to the best results. 11 is main-tained that 3,5-dimethyl substitution is not superior ; to 3,5-dichloro subs-titution. Taking as an example the 3,5-dichloro substitution,it is stated moreover that the activity increases from propylamide through the allylamide to propargylamide, the activity being further strengthened by dimethyl substitution at the first carbon atom of the alkyl radical.
It is the object of the present invention to provide a herbicide having a selective phytotoxic effect which, while having a high tolerance to useful plants, has a high efective-ness against undesirable plants in agricultural and horti-cultural areas, or any other areas under cultivation.
It has been found, according to the invention, that the desirable effect is achieved by benzamide compounds, which do not have 3,5-dichloro substitution, but 3,5-climethyl substitution, and which do not exhibit dimethyl substitution at the first carbon atom of the alkyl radical. These two differences in the structure of the molecule should, in accordance with the cited studies, lead to a decxease in herbicidal effectiveness.
In view of the above-mentioned studies it could not be expected and is therefore surprising that tha compounds ~lZ~1~8~:
of the invention are of such high herbicidal potency, while having at the same time an improved selecti~:ity, that is to say, having a high tolerance to useful plant~. Thus, the compounds according to -the invention are equal to or surpass the known 3,5-dichloro-N-(dimethylpropinyl)--benzamide in their herbicidal effectiveness.
The extreme importance of these new agents for agricultural purposes will be demons-trated by the following example of winter rape:
Winter rape is sown in the fall after other important ~gricultural plants, e.g. grains, are sown. It is a known fact that a considerable amount of grain is lost before the harvest and during the threshing which results in individual grains dropping to the soil. These grains germinate after the following cultiva-tion as so-called l'off-grade grain" or "scatterings". As these grains grow, they constitute a considerable rival for the wintex rape, since they take up some of the available water J nutrients, light and space. They cannot be tolerated because they lead to a high reduction in yield.
It is therefore of great significance to modern agriculture to provide a herbicide which combats the off-grade grains and the various weeds, while saving the useful plants of the cultivation.
The herbicidal effect oE the compounds according to the invention extends, first of all, to highly yield-8~
reducing weeds, such as e.g. wild oats, foxtail; meadowgcass (e.g., hair grass, thyrsus grass, brome grass and poa spec;es), true grasses, (e.g., wind grass, rye grass, dogstail), species of millet grasses (e.g., chick corn, bristle millet) and to off-grade grains in general (for example, wheat, barley, rye, oats) and important dicotyledonous weeds (such as, e.g., knot plants, speedwell, deadnettle, chickweed and others).
Examples of other agricultural and horticultural cultivations in which the agents according to the - invention are used for selective effect are: rape, mustard, alfalfa, potatoes, vegetable cabbages (e.g., white cabbage, red cabbage, cauliflower), radishes, lettuce, endives, sunflowers, ar-tichokes, and ornamental shrubs from the family of compositae (e.g., -~
chrysanthemums, asters and dahlias).
The preparation of the new compounds according to the invention may be carried out in a manner known per se, by starting with 3,5-dimethyl benzoic acid, which is commercially available. This compound is then converted into the acid chloride by treatment with thionyl chloride or phosphorus pentachloride, preferably in the presence of an inert solvent (e.g., benzene, toluene, petrol ether, or chloroform), at temperatures of 20C
to 120C. In the next step of the reaction, the acid chloride is reacted with allylamine or propargylamine at temperatures from 20C to 120C to form the corresponding amide. In order to neutralize the hydrochloric acid formed in the reaction, ~..j, ?f~
an excess amount of amine is added, or one operates in the presence oE an auxiliary base (e.g., triethylamine or pyridine).
As previously m2ntioned, the compounds according to the invention may be used ~ se or in mixture In general, they are used in mixtures with solid or liquid diluents or in solutions with solid or li~uid solvents, with an amount of effective agent from 0.01 to 95% by weight.
The mixtures or solutions, respectively, are generally in the form of emulsion concentrates, pastes, spray powders, granulates, or microcapsules.
Emulsion concentrates as a rule contain 10 - 60 preferably 15 - 40%, by weight of the effective agent,
CH3~CH3 wherein R represents a vinyl or ethinyl radical. The inven-tion also relates to the use of such compounds as herbicides per se, or in combination with other pesticidal or herbicidal substances. Preferably, they are used in the ~orm of liquid or solid mixtures, or liquid or solid solutions.
A number of substances of the benzam:ide series are already known which have herbicidal properties. U.S. patents 3,534,098 and 3,640,699 describe 3,5-disubstituted 1,1-dimethylpropinyl henzamides and their use as herbicides. As substituents in the 3,5 positions, F,Cl,Br or the methyl radical are mentioned. U.S. patent 3,551,484 describes N-(l,l-dimethyl-propenyl) -3,5-disubstituted benzamide 5 and their herbicidal properties.
From this series, the 3,5-dichloro-N-(l,l-dimethyl~
propinyl)-benzamide, which is sold commercially under the trademark "KERB", has achie~ed particular importance; this compound has, however, in its phytotoxic activity, the drawback of low tolerance to a number of useful plants.
In J. Agr. Food Chem., Vol. 19, No. 3, 1971, p. 417-21, the relationships between structure and herbiciclal ~., 9~3~Z
activity are studied on a number of benzamides, which have a similar skructure to 3,5-dichloro-N-(1,1-dlmethylpropinyl)-benzamide. In this article it is shown that di-substikution at the aromatic radical leads to the best results. 11 is main-tained that 3,5-dimethyl substitution is not superior ; to 3,5-dichloro subs-titution. Taking as an example the 3,5-dichloro substitution,it is stated moreover that the activity increases from propylamide through the allylamide to propargylamide, the activity being further strengthened by dimethyl substitution at the first carbon atom of the alkyl radical.
It is the object of the present invention to provide a herbicide having a selective phytotoxic effect which, while having a high tolerance to useful plants, has a high efective-ness against undesirable plants in agricultural and horti-cultural areas, or any other areas under cultivation.
It has been found, according to the invention, that the desirable effect is achieved by benzamide compounds, which do not have 3,5-dichloro substitution, but 3,5-climethyl substitution, and which do not exhibit dimethyl substitution at the first carbon atom of the alkyl radical. These two differences in the structure of the molecule should, in accordance with the cited studies, lead to a decxease in herbicidal effectiveness.
In view of the above-mentioned studies it could not be expected and is therefore surprising that tha compounds ~lZ~1~8~:
of the invention are of such high herbicidal potency, while having at the same time an improved selecti~:ity, that is to say, having a high tolerance to useful plant~. Thus, the compounds according to -the invention are equal to or surpass the known 3,5-dichloro-N-(dimethylpropinyl)--benzamide in their herbicidal effectiveness.
The extreme importance of these new agents for agricultural purposes will be demons-trated by the following example of winter rape:
Winter rape is sown in the fall after other important ~gricultural plants, e.g. grains, are sown. It is a known fact that a considerable amount of grain is lost before the harvest and during the threshing which results in individual grains dropping to the soil. These grains germinate after the following cultiva-tion as so-called l'off-grade grain" or "scatterings". As these grains grow, they constitute a considerable rival for the wintex rape, since they take up some of the available water J nutrients, light and space. They cannot be tolerated because they lead to a high reduction in yield.
It is therefore of great significance to modern agriculture to provide a herbicide which combats the off-grade grains and the various weeds, while saving the useful plants of the cultivation.
The herbicidal effect oE the compounds according to the invention extends, first of all, to highly yield-8~
reducing weeds, such as e.g. wild oats, foxtail; meadowgcass (e.g., hair grass, thyrsus grass, brome grass and poa spec;es), true grasses, (e.g., wind grass, rye grass, dogstail), species of millet grasses (e.g., chick corn, bristle millet) and to off-grade grains in general (for example, wheat, barley, rye, oats) and important dicotyledonous weeds (such as, e.g., knot plants, speedwell, deadnettle, chickweed and others).
Examples of other agricultural and horticultural cultivations in which the agents according to the - invention are used for selective effect are: rape, mustard, alfalfa, potatoes, vegetable cabbages (e.g., white cabbage, red cabbage, cauliflower), radishes, lettuce, endives, sunflowers, ar-tichokes, and ornamental shrubs from the family of compositae (e.g., -~
chrysanthemums, asters and dahlias).
The preparation of the new compounds according to the invention may be carried out in a manner known per se, by starting with 3,5-dimethyl benzoic acid, which is commercially available. This compound is then converted into the acid chloride by treatment with thionyl chloride or phosphorus pentachloride, preferably in the presence of an inert solvent (e.g., benzene, toluene, petrol ether, or chloroform), at temperatures of 20C
to 120C. In the next step of the reaction, the acid chloride is reacted with allylamine or propargylamine at temperatures from 20C to 120C to form the corresponding amide. In order to neutralize the hydrochloric acid formed in the reaction, ~..j, ?f~
an excess amount of amine is added, or one operates in the presence oE an auxiliary base (e.g., triethylamine or pyridine).
As previously m2ntioned, the compounds according to the invention may be used ~ se or in mixture In general, they are used in mixtures with solid or liquid diluents or in solutions with solid or li~uid solvents, with an amount of effective agent from 0.01 to 95% by weight.
The mixtures or solutions, respectively, are generally in the form of emulsion concentrates, pastes, spray powders, granulates, or microcapsules.
Emulsion concentrates as a rule contain 10 - 60 preferably 15 - 40%, by weight of the effective agent,
2 - 25% by weight of dispersion auxiliaries and organic solvents and/or water. Spraying powders usually contain 10 - 80%, preferably 15 - 70%, by weight of the ~ffective agent, 1 - 10% by weight of dispersion auxiliaries~ and 10 - 89% by weight of inert ingredients. Granulates and microcapsules contain in addition to inext ingredients, binders and/or coatings, and 1 - 10%, preEerably 5 10~, by weight of the active agent.
As dispersing agents used in accordance with the invention, alkyl and aryl sulfonates, methyl cellulo~e, polymeric sulfonic acids and their salts, polyalcohols, .Z9~Z
fatty acid esters, fatty alcohol ethers and fatty amines are suitable. Organic solvents suitabl~ for use are, e.g., alcohols, such a~ ethanol, butanol, climethyl-formamide (D~F), dimethylsulfoxide tDMSO), N-m~!thylpyr-rolidone and aromatics, such as toluene and xylene.
As inert ingredients, the following, e.g., are suitable: kaolin, china-clay, talcum, calcium carbonate, highly dispersed silica, silicon gels, kieselguhr,diatomaceous earth, pumice,brick chips, corn husks and thickening agents such as starch and carboxy-methylcellulose. Suitable hinders include, e.g., magnesium sulfate, gypsum and gum arabic.
Suitable formulations of herbicides with agents according to the invention include, e.g~, the following:
1. Emulsion concentrate:
20% by weight of effective agent 50% by weight of isopropanol 20~ by weight of xYlene 10% by weight of extenders and binders of the firm Atlas-Chemie, Essen, West Germany, sold under the trademark "Atplus 526."
2. Spraying powders:
20% by weight of effective agent 44% by weight of China-clay 16% by weight of highly dispersed silica 15% by weight of lignin sulfonate ~Cellulose pitch) 5% by weight of sodium-alkylnaphthalene ~ulfonate-formaldehyde-condensate sold under the trademark "Atlox 4862."
In general, the efect.ive agents are used in amounts o~ O.S - 8 kg/ha and, preferably, 2 - 4 kg/ha.
The application as herbicides may be carried out on the plants (post-emergence process) or ~y direGt application to a surface of the soll free of vegetat.ion (pre-emergence or pre-seeding process). Better herbicidal effects are obatined by application o the herbicides to the soil, preferably before sowing of cult.ivated plants, with working of the agents into the 10 uppermost layers of the so.il with mechanical means so as to form flat strata in the soil.
In the following, the preparation of the herbicides according to the invention will be more fully illustrated by a number of examples, which will also demonstrate the herbicidal properties of the products per se and in comparison with known herbicides. It should, however, be understood that these examples are given by way of illustration only and not by limitation.
Preparation of 3,5-dimethyl-benzallylamide:
Step .l:
Into a three-neck flask with stirrer and refulx cooler, 170 g (1.13 mol) of 3,5-dimethyl benzoic acid are introduced together with 1,500 g toluene and about 2 g N,N-dimethylformamide, and heated to abou~ 70C~ 202 g (1.7 mol) of thionyl chloride are added dropwise and heated .
Z~8~3Z
under reflux, until the gas development has ceased. Then, the excess amount of thionyl chloride and the solvent axe withdrawn and the residue is d.istilled in vacuo. Obtained are 182.7 g of 3,5-dimethyl-benzoic acid chloride, which is 95.9% of the theoretical amount.
Step 2:
74 g (1.3 mol) of allylamine and 131 g (1.3 mol) of triethylamine are introduced, together with l,800 g of toluene, into a reaction flask and heated to about 70C.
To this, 182 g (1.08 mol) of 3,5-dimethyl-benzoic acid chloride mixed with 200 g of toluene are added drop by drop within an hour, and further stirring is carried out at 70 - 80C for one hour. After having filtered off the triethylaminehydro chloride, washing with water follows to effect neutrality and the toluene is withdrawn under reduced pressure. As reaction product, 201 g of 3,5~dimethyl-benzallylamide are obtained, which is sufficiently pure for most purposes; it is a reddish-brown oil and corresponds to 98.5% of the theoretical yield. If further purification of the product is desired, it can be distilled at a temperature of I40 - 145C and a pressure o 0.05 Torr ~ 6.7 N/m2. The distillate solidiies to a wax-like mass having a melting point of 40 - 42C.
~ 8 l~Z~
Example 2 Preparation o~ 3,5-dime-thyl-benzoic acid propargylamide.
The preparation of the acid chloride is carried out as in Example 1.
In the second step, 200 ml of toluene, 3 g (0.054 mol) of propargylamine, and 5.5 g (0.054 mol) of triethylamine are introduced into a three-neck flask equipped with a stirrer and reflux cooler. Then, 9.2 g (0.054 mol) of 3,5-dimethyl-benzoic chloride are added drop by drop and the mixture is heated for two hours under reflux. The mixture is cooled and filtered, and the filtrate washed with a total of 150 ml of water. While washing, part of the product is already precipitated, which is filtered off. The toluene phase is concentrated to about 40 ml at which time a further amount of product is obtained in the form of white crystals. After drying in a drying chamber a yield of 7.5 g (73.6% of the theoretical) of 3,5-dimethyl-benzoic acid propargylamide is obtained.
Example 3 The herbicidal effectiveness of the products according to the invention was tested using them once in a hot house. In the described test, the seed grains of the cultivated plants and the weeds were sown in a mineral-containing soil of a field poor in humus, and lightly covered with soil particles. I~mediately after the sowing, ln any case before germination took place, the herbicides according _ g -to the invention were uniformly sprayed onto the veyetation-free area in the form of spraying powders or emulsion con~
centrates.
Four weeks after the treatment, the plants were finally tested for damage or total destruction, with control - plants serving as a reference which grew up in the meanwhile without having been treated.
Effectiveness in ~ with the use of 0.5 - 8 kg/ha of effective agent in the pre-emergence process.
1 year culti- ............ old off~
vàted -sugar wild.-meadow- - grade ~ k~/ha' mustard beet' oats` qrass foxtail.'~rain .. 0~.'5~ '"'0 '' "'"'`'0'"''
As dispersing agents used in accordance with the invention, alkyl and aryl sulfonates, methyl cellulo~e, polymeric sulfonic acids and their salts, polyalcohols, .Z9~Z
fatty acid esters, fatty alcohol ethers and fatty amines are suitable. Organic solvents suitabl~ for use are, e.g., alcohols, such a~ ethanol, butanol, climethyl-formamide (D~F), dimethylsulfoxide tDMSO), N-m~!thylpyr-rolidone and aromatics, such as toluene and xylene.
As inert ingredients, the following, e.g., are suitable: kaolin, china-clay, talcum, calcium carbonate, highly dispersed silica, silicon gels, kieselguhr,diatomaceous earth, pumice,brick chips, corn husks and thickening agents such as starch and carboxy-methylcellulose. Suitable hinders include, e.g., magnesium sulfate, gypsum and gum arabic.
Suitable formulations of herbicides with agents according to the invention include, e.g~, the following:
1. Emulsion concentrate:
20% by weight of effective agent 50% by weight of isopropanol 20~ by weight of xYlene 10% by weight of extenders and binders of the firm Atlas-Chemie, Essen, West Germany, sold under the trademark "Atplus 526."
2. Spraying powders:
20% by weight of effective agent 44% by weight of China-clay 16% by weight of highly dispersed silica 15% by weight of lignin sulfonate ~Cellulose pitch) 5% by weight of sodium-alkylnaphthalene ~ulfonate-formaldehyde-condensate sold under the trademark "Atlox 4862."
In general, the efect.ive agents are used in amounts o~ O.S - 8 kg/ha and, preferably, 2 - 4 kg/ha.
The application as herbicides may be carried out on the plants (post-emergence process) or ~y direGt application to a surface of the soll free of vegetat.ion (pre-emergence or pre-seeding process). Better herbicidal effects are obatined by application o the herbicides to the soil, preferably before sowing of cult.ivated plants, with working of the agents into the 10 uppermost layers of the so.il with mechanical means so as to form flat strata in the soil.
In the following, the preparation of the herbicides according to the invention will be more fully illustrated by a number of examples, which will also demonstrate the herbicidal properties of the products per se and in comparison with known herbicides. It should, however, be understood that these examples are given by way of illustration only and not by limitation.
Preparation of 3,5-dimethyl-benzallylamide:
Step .l:
Into a three-neck flask with stirrer and refulx cooler, 170 g (1.13 mol) of 3,5-dimethyl benzoic acid are introduced together with 1,500 g toluene and about 2 g N,N-dimethylformamide, and heated to abou~ 70C~ 202 g (1.7 mol) of thionyl chloride are added dropwise and heated .
Z~8~3Z
under reflux, until the gas development has ceased. Then, the excess amount of thionyl chloride and the solvent axe withdrawn and the residue is d.istilled in vacuo. Obtained are 182.7 g of 3,5-dimethyl-benzoic acid chloride, which is 95.9% of the theoretical amount.
Step 2:
74 g (1.3 mol) of allylamine and 131 g (1.3 mol) of triethylamine are introduced, together with l,800 g of toluene, into a reaction flask and heated to about 70C.
To this, 182 g (1.08 mol) of 3,5-dimethyl-benzoic acid chloride mixed with 200 g of toluene are added drop by drop within an hour, and further stirring is carried out at 70 - 80C for one hour. After having filtered off the triethylaminehydro chloride, washing with water follows to effect neutrality and the toluene is withdrawn under reduced pressure. As reaction product, 201 g of 3,5~dimethyl-benzallylamide are obtained, which is sufficiently pure for most purposes; it is a reddish-brown oil and corresponds to 98.5% of the theoretical yield. If further purification of the product is desired, it can be distilled at a temperature of I40 - 145C and a pressure o 0.05 Torr ~ 6.7 N/m2. The distillate solidiies to a wax-like mass having a melting point of 40 - 42C.
~ 8 l~Z~
Example 2 Preparation o~ 3,5-dime-thyl-benzoic acid propargylamide.
The preparation of the acid chloride is carried out as in Example 1.
In the second step, 200 ml of toluene, 3 g (0.054 mol) of propargylamine, and 5.5 g (0.054 mol) of triethylamine are introduced into a three-neck flask equipped with a stirrer and reflux cooler. Then, 9.2 g (0.054 mol) of 3,5-dimethyl-benzoic chloride are added drop by drop and the mixture is heated for two hours under reflux. The mixture is cooled and filtered, and the filtrate washed with a total of 150 ml of water. While washing, part of the product is already precipitated, which is filtered off. The toluene phase is concentrated to about 40 ml at which time a further amount of product is obtained in the form of white crystals. After drying in a drying chamber a yield of 7.5 g (73.6% of the theoretical) of 3,5-dimethyl-benzoic acid propargylamide is obtained.
Example 3 The herbicidal effectiveness of the products according to the invention was tested using them once in a hot house. In the described test, the seed grains of the cultivated plants and the weeds were sown in a mineral-containing soil of a field poor in humus, and lightly covered with soil particles. I~mediately after the sowing, ln any case before germination took place, the herbicides according _ g -to the invention were uniformly sprayed onto the veyetation-free area in the form of spraying powders or emulsion con~
centrates.
Four weeks after the treatment, the plants were finally tested for damage or total destruction, with control - plants serving as a reference which grew up in the meanwhile without having been treated.
Effectiveness in ~ with the use of 0.5 - 8 kg/ha of effective agent in the pre-emergence process.
1 year culti- ............ old off~
vàted -sugar wild.-meadow- - grade ~ k~/ha' mustard beet' oats` qrass foxtail.'~rain .. 0~.'5~ '"'0 '' "'"'`'0'"''
3,5-Dimethyl- 1 0 0 100 100 75 95 Benzallylamide 2 0 0 100 100 90 100 .4 0 10 100 100 100 100 . 8 10 20 100 100 100 100 __ __ ~ _ .
: 0.5 0 0 70 90 75 60 3,5-Dimethyl- 1 0 0 85 100 95 80 benzoic-pro- 2 0 0 100 100 98 100 pargylamide 4 0 0 100 100 100 100 . ~ . ..
Comparison Exam~le 1 For comparison, tests were carried out with a commercial herbicide, 'IKERB 50 Wl'*,~ which has been used extensively for combating weeds and undesirable grass species, on the one hand, and 3,5-dichloro~benzallylamide, on the other hand, the criteria used being as described in Example 3.
Effectiveness in % with the use of 0.5 - 8 kg/ha effective substance.
* Trade Mark . ,~, 1 year kg/ha culti- old of-Eff. vated sugar wild meadow grade Aqent mustard beet oats q~ass foxtail qrain - _ 0.5 10 65 `` 95 ~5 90 65 Propyzamide 1 40 85 100 100 100 75 (KERB 50 W)* 2 95 90 100 100 100 95
: 0.5 0 0 70 90 75 60 3,5-Dimethyl- 1 0 0 85 100 95 80 benzoic-pro- 2 0 0 100 100 98 100 pargylamide 4 0 0 100 100 100 100 . ~ . ..
Comparison Exam~le 1 For comparison, tests were carried out with a commercial herbicide, 'IKERB 50 Wl'*,~ which has been used extensively for combating weeds and undesirable grass species, on the one hand, and 3,5-dichloro~benzallylamide, on the other hand, the criteria used being as described in Example 3.
Effectiveness in % with the use of 0.5 - 8 kg/ha effective substance.
* Trade Mark . ,~, 1 year kg/ha culti- old of-Eff. vated sugar wild meadow grade Aqent mustard beet oats q~ass foxtail qrain - _ 0.5 10 65 `` 95 ~5 90 65 Propyzamide 1 40 85 100 100 100 75 (KERB 50 W)* 2 95 90 100 100 100 95
4 9~ 95 100 100 100 100 _ _ 0.5 10 10- ~7~ 77r~-----er--~
3,5-Dimethyl- 1 40 25 75 85 45 65 Benzallylamide 2 50 40 95 98 60 95 4 75 75 100 1(;)0 75 98 _ _ 8_ 9 Q _ 85 100 1(~ U~
Example 3 and Comparison Example 1 clearly show the remarkably superior tolerance of cultivated plants (useful plants) by treatment with the herbicides according to the invention as compared to known herbicides, the activity towards weeds and undesirable grasses being equal. The comparison of 3,5-dichlorobenzallylamide with the compound of the invention, 3,5-dimethylbenzallylamide,demonstrates the critical importance of the 3,5-dimethyl position in the herbicides behavior towards cultivated plants.
Example 4 In a further test series, the effectiveness of the products of the invention when used in the pre-seeding process with working into the soil. Herbicides are g~nerally worked into the uppermost layer of the soil, if an improve-ment of the effectiveness against the undesirable weeds and the like can be accomplished~ for instance, in existing dryness of the soil. In the above process, effec-tive agents are evenly sprayed onto the vegetation-free 50il in the form of e-mulsion concentrates or spraying powders.
*Trade Mark ~.
Immediately after the spraying, the agents are worked into the uppermost soil surface by means of a rake to a depth oE 2 - 3 cm. 24 hours thereafter, t.he sesdin~
of grains of cultivated plants and weeds is carried out into the herbicide--treated soil surface. The final testing for damage or total destruction of the plants takes place four weeks after the ~reatment, with control plants serving as a, - reference, which grew up in the meanwhile without having been treated.
Activity in % with the use of effective ingredient of 1 kg/ha in the pre-seeding process with mechanical work-in.
1 year off- old winter- sugar grade wild meadow fox- knot kq/ha raFe beet qrain oats qrass tail weed _ ~ . _ __ 3,5-Dimethyl-Benzallylamide 1 O O 98 100 100 98 100 . .
3,5-Dimethyl-Benzoic- 1 O O100 100 100 9598 propargyl-amide Comparison Example 2 The compounds used for comparison are commercially obtainable herbicides, which have been used for quite some time for pest control in winter rape and sugar beets in a pre-seeding process followed by work-in~ In addition, 3,5-dichlorobenzallylamide is used for comparison as in the Comparison Example 1. Otherwise, the procedure was the same as in Example 4.
Lzg~38~:
Effec-tiveness in ~ with -the use o 1 kg/ha o effective agen-t in the pre-seeding 2rocess with work-in.
1 year o~f~ old winter- sugar grade wild nead~ fox- knot .~ . kg/ha rape } t grain oats grass tail weed Triflura-lin 1 40 95 75 95 100100 95 (Elancolan) Triallate ~Avadex BW) k 1 O 100 100 100 0 3,5-di-chloro- .
benzallyl- 1 60 35 95 100 10070 85 amide __ _ _ Example 4 shows, taken together with Comparison Example 2, the superior tolerance of the herbicides accord-ing to the invention to cultivated plants, when compared to conventional herbicides, the effect on weeds being equal in both cases.
* Trade Mark .~t - 13 -
3,5-Dimethyl- 1 40 25 75 85 45 65 Benzallylamide 2 50 40 95 98 60 95 4 75 75 100 1(;)0 75 98 _ _ 8_ 9 Q _ 85 100 1(~ U~
Example 3 and Comparison Example 1 clearly show the remarkably superior tolerance of cultivated plants (useful plants) by treatment with the herbicides according to the invention as compared to known herbicides, the activity towards weeds and undesirable grasses being equal. The comparison of 3,5-dichlorobenzallylamide with the compound of the invention, 3,5-dimethylbenzallylamide,demonstrates the critical importance of the 3,5-dimethyl position in the herbicides behavior towards cultivated plants.
Example 4 In a further test series, the effectiveness of the products of the invention when used in the pre-seeding process with working into the soil. Herbicides are g~nerally worked into the uppermost layer of the soil, if an improve-ment of the effectiveness against the undesirable weeds and the like can be accomplished~ for instance, in existing dryness of the soil. In the above process, effec-tive agents are evenly sprayed onto the vegetation-free 50il in the form of e-mulsion concentrates or spraying powders.
*Trade Mark ~.
Immediately after the spraying, the agents are worked into the uppermost soil surface by means of a rake to a depth oE 2 - 3 cm. 24 hours thereafter, t.he sesdin~
of grains of cultivated plants and weeds is carried out into the herbicide--treated soil surface. The final testing for damage or total destruction of the plants takes place four weeks after the ~reatment, with control plants serving as a, - reference, which grew up in the meanwhile without having been treated.
Activity in % with the use of effective ingredient of 1 kg/ha in the pre-seeding process with mechanical work-in.
1 year off- old winter- sugar grade wild meadow fox- knot kq/ha raFe beet qrain oats qrass tail weed _ ~ . _ __ 3,5-Dimethyl-Benzallylamide 1 O O 98 100 100 98 100 . .
3,5-Dimethyl-Benzoic- 1 O O100 100 100 9598 propargyl-amide Comparison Example 2 The compounds used for comparison are commercially obtainable herbicides, which have been used for quite some time for pest control in winter rape and sugar beets in a pre-seeding process followed by work-in~ In addition, 3,5-dichlorobenzallylamide is used for comparison as in the Comparison Example 1. Otherwise, the procedure was the same as in Example 4.
Lzg~38~:
Effec-tiveness in ~ with -the use o 1 kg/ha o effective agen-t in the pre-seeding 2rocess with work-in.
1 year o~f~ old winter- sugar grade wild nead~ fox- knot .~ . kg/ha rape } t grain oats grass tail weed Triflura-lin 1 40 95 75 95 100100 95 (Elancolan) Triallate ~Avadex BW) k 1 O 100 100 100 0 3,5-di-chloro- .
benzallyl- 1 60 35 95 100 10070 85 amide __ _ _ Example 4 shows, taken together with Comparison Example 2, the superior tolerance of the herbicides accord-ing to the invention to cultivated plants, when compared to conventional herbicides, the effect on weeds being equal in both cases.
* Trade Mark .~t - 13 -
Claims (14)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS
1. A compound of the formula wherein R represents a member of the group consisting of a vinyl and ethinyl radical.
2. A compound according to Claim 1, wherein R
represents a vinyl radical.
represents a vinyl radical.
3. A compound according to Claim 1, wherein R
represents an ethinyl radical.
represents an ethinyl radical.
4. A process for producing a herbicide comprising a compound of the formula wherein R represents a member of the group consisting of a vinyl and ethinyl radical, comprising the steps of:
reacting 3,5-dimethylbenzoic acid with thionyl chloride to form the corresponding acid chloride; and converting said chloride into the corresponding amide by reaction with a compound selected from the group consisting of allylamine and propargylamine.
reacting 3,5-dimethylbenzoic acid with thionyl chloride to form the corresponding acid chloride; and converting said chloride into the corresponding amide by reaction with a compound selected from the group consisting of allylamine and propargylamine.
5. The process according to Claim 4, wherein said converting step is effected in the presence of an auxiliary base.
6. The process according to Claim 5, wherein said auxiliary base is a member selected from the group consisting of triethylamide or pyridine.
7. A method of killing undesired vegetation comprising applying to the locus to be treated a compound of the formula wherein R represents a member of the group consisting of a vinyl and ethinyl radical.
8. The method according to Claim 7, wherein said compound is applied in the form of an emulsion concentrate comprising 10-60% by weight of said compound as the effective agent, 2-25% by weight of dispersion auxiliaries and organic solvents and/or water.
9. The method according to Claim 7, wherein said compound is applied in the form of a spraying powder containing 10-80% by weight of said compound as the effective agent, 1-10% by weight of dispersion auxiliaries, and 10-89% by weight of inert ingredients.
10. The method according to Claim 7, wherein said compound is applied in the form of a granulate or microcapsule containing 1-10% by weight of said compound as the effective agent, inert ingredients and bindings and/or coatings.
11. The method according to Claim 7, wherein said compound is used in an amount of 0.5-8 kg/ha.
12. The method according to Claim 7, wherein said compound is used in a pre-seeding process and is worked into the soil mechanically,
13. The method according to Claim 7, wherein said compound is in admixture with a diluent selected from the group consisting of a solid diluent and a liquid diluent.
14. The method according to Claim 7, wherein said compound is dissolved in a solvent selected from the group consisting of a liquid solvent and a solid solvent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792926982 DE2926982A1 (en) | 1979-07-04 | 1979-07-04 | BENZAMIDE DERIVATIVES AS HERBICIDES |
| DEP2926982.7 | 1979-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1129882A true CA1129882A (en) | 1982-08-17 |
Family
ID=6074880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA353,781A Expired CA1129882A (en) | 1979-07-04 | 1980-06-11 | Benzamide derivatives and their use as herbicides |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0022249B1 (en) |
| JP (1) | JPS5610158A (en) |
| AT (1) | ATE352T1 (en) |
| CA (1) | CA1129882A (en) |
| DE (2) | DE2926982A1 (en) |
| ES (1) | ES8107003A1 (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3534098A (en) * | 1967-01-10 | 1970-10-13 | Rohm & Haas | 3,5-disubstituted benzamides |
| US3640699A (en) * | 1967-01-10 | 1972-02-08 | Rohm & Haas | 3 5-disubstituted benzamides |
| US3652670A (en) * | 1968-12-05 | 1972-03-28 | Abbott Lab | Substituted propargyl benzamides |
| FR2186190A1 (en) * | 1972-05-29 | 1974-01-11 | Pepro | Fungicidal chlorobenzamide compsns - for treating fungal disease of plants |
| US4054576A (en) * | 1973-11-19 | 1977-10-18 | Stauffer Chemical Company | Insect repellant compounds |
-
1979
- 1979-07-04 DE DE19792926982 patent/DE2926982A1/en not_active Withdrawn
-
1980
- 1980-04-30 JP JP5772880A patent/JPS5610158A/en active Pending
- 1980-06-11 CA CA353,781A patent/CA1129882A/en not_active Expired
- 1980-07-03 EP EP80103785A patent/EP0022249B1/en not_active Expired
- 1980-07-03 AT AT80103785T patent/ATE352T1/en not_active IP Right Cessation
- 1980-07-03 DE DE8080103785T patent/DE3060073D1/en not_active Expired
- 1980-07-03 ES ES493060A patent/ES8107003A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES493060A0 (en) | 1981-08-16 |
| DE2926982A1 (en) | 1981-01-22 |
| ES8107003A1 (en) | 1981-08-16 |
| ATE352T1 (en) | 1981-11-15 |
| DE3060073D1 (en) | 1982-01-14 |
| EP0022249A1 (en) | 1981-01-14 |
| JPS5610158A (en) | 1981-02-02 |
| EP0022249B1 (en) | 1981-11-04 |
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Legal Events
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|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19990817 |