US3098001A - Acaricide agent - Google Patents

Acaricide agent Download PDF

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Publication number
US3098001A
US3098001A US102080A US10208060A US3098001A US 3098001 A US3098001 A US 3098001A US 102080 A US102080 A US 102080A US 10208060 A US10208060 A US 10208060A US 3098001 A US3098001 A US 3098001A
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Prior art keywords
spider mites
attack
agents
benzyl
formula
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US102080A
Inventor
Werres Horst
Czyzewski Alfred
Jager Albert
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Bayer Pharma AG
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Schering AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals

Definitions

  • the present invention relates to a new aoaricide agent, and more particularly to agents for com-batting plant damaging spider mites.
  • the present invention mainly comprises an acaricide composition
  • a carrier and a compound of the formula:
  • R is selected from the group consisting of hydrogen and alkyl, wherein R is alkyl, wherein X is selected from the group consisting of oxygen and sulfur, wherein X is selected from the group consisting of oxygen and sulfur, and wherein R is selected from the group consisting of benzyl and halogen-substituted benzyl radical-s.
  • R is either hydrogen or an alkyl, and when it is an alkyl it is preferably a lower alkyl and most preferably methyl. Likewise, R which is an alkyl is preferably a lower alkyl and most preferably methyl.
  • the substituent R is either benzyl or a halogen-substituted benzyl.
  • R is a halogen-substituted benzyl it is a benzyl substituted by one or more halogens, most preferably by chlorine and/ or bromine.
  • the compounds which are used according to the present invention are partially known compounds which can be produced by known methods, for example by the reaction of the corresponding substituted benzyl halogenide with the salt (preferably the alkali metal or ammonium salt) of the corresponding carbamic acid, for example the monothiocarbamic acid or the dithiocarb amic acid.
  • the salt preferably the alkali metal or ammonium salt
  • acaricidal agents of the present invention have been found to be much more eflfective than O-phenyl esters or S-phenyl esters of carbamic acids or monothiocarbamic acid-s.
  • the compounds of the present invention may be used in various acaricidal dosages in application thereof to an area subject to spider mites attack in order to combat such spider mites attack, and the range of dosage may vary quite considerably in view of the fact that very low dosages are efiiective, and very high dosages are compatible with continuation of the plant life.
  • the agents can be applied with any carrier commonly used for agents of this type, and in any form, for example in the form of a suspension, emulsion, powder, solution, aerosol, or the like.
  • the agents may be applied alone or in admixture with other insecticides, fungicides, or the like.
  • suitable liquid and solid carriers for the compounds of the present invention are water, mineral oils, organic solvents, emulsifying or suspending agents, bentonite, fullers earth, gypsum, lime, diatomaceous earth, pyrophyllite, silica, talc, chalk, or the like.
  • Emulsifiers, wetting agents or binding agents may be added to the preparations as well as carrier gases, odoriferous substances, substances for attracting, or repellants.
  • the preparations can be in the form of dust, agents for spreading, gnanulates, for spraying, atomizable liquids, aerosols, etc.
  • the amount of the active substance of the compounds of this invention which are used in the preparations for combatting spider mites may vary in ample limits. It depends on the kind of formulation, the kind of application, the desired measure of control and the kind of the pests to be combatted. Depending on the kind of preparation the amount of active substance in the agent may be about 0.1 to 90 percent by weight.
  • the agents may be applied in concentrations as low as 0.01 percent by weight. Usually good results are received by concentrations between about 0.025 and 10 percent in liquid or solid carriers. For special purposes higher concentrations may be desired for instance as high as about 20 percent.
  • R is selected from the group consisting of hydrogen and alkyl, wherein R is alkyl, wherein X is selected from the group consisting of oxygen and sulfur, wherein X is selected from the group consisting of oxygen and sulfur, and wherein R is selected from the group consisting of benzyl and halogen-substituted benzyl radicals.
  • R is selected from the group consisting of hydrogen and alkyl, wherein R is alkyl, wherein X is selected from the group consisting of oxygen and sulfur, wherein X is selected from the group consisting of oxygen and sulfur, and wherein R is selected from the group consisting of benzyl and halogen-substituted benzyl radicals.
  • R is p-chlorobenzyl
  • R is benzyl
  • R is p-chlorobenzyl
  • NCSR CH3 0 wherein R is p-chlorobenzyl.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

3,098,001 ACARICIDE AGENT Horst Werres, Rerlin-Charlottenburg, Alfred Czyzewski, Berlin-Tempelhof, and Albert Jager, Berlin-Hermsdorf, Germany, assignors to Schering A.G., Berlin, Germany No Drawing. Filed Dec. 28, 1960, Ser. No. 102,080 Claims priority, application Germany Dec. 28, 1959 (Ilaims. (Cl. 167-30) The present invention relates to a new aoaricide agent, and more particularly to agents for com-batting plant damaging spider mites.
Various chemicals have been suggested for combat-ting plant damaging mites, for example the fred spider. However, in most cases the agent used is only effective against certain development stages of the spider mites so that a complete destruction has not been obtainable prior to the present invention.
It is particularly true that the initial action of the known acaricides is too low, or the same are only effective as ovicides. In addition, it has been particularly difiicult to develop acaricides which are both effective and which are compatible with plants.
It is accordingly a primary object of the present invention to provide an acaricidal agent which avoids all of the above mentioned disadvantages of the known agents.
It is another object of the present invention to provide a new acaricide agent which is highly effective against all development stages of spider mites, and which in addition is compatible with plants.
It is yet another object of the present invention to provide a plant-compatible acaricidal agent which is highly effective against all development stages of plant damaging parasites such as the spider mites, etc.
Other objects and advantages of the present invention will be apparent from a further reading of the specification and of the appended claims.
With the above and other objects in view, the present invention mainly comprises an acaricide composition comprising a carrier and a compound of the formula:
wherein R is selected from the group consisting of hydrogen and alkyl, wherein R is alkyl, wherein X is selected from the group consisting of oxygen and sulfur, wherein X is selected from the group consisting of oxygen and sulfur, and wherein R is selected from the group consisting of benzyl and halogen-substituted benzyl radical-s.
The substituent R as indicated above is either hydrogen or an alkyl, and when it is an alkyl it is preferably a lower alkyl and most preferably methyl. Likewise, R which is an alkyl is preferably a lower alkyl and most preferably methyl.
As indicated, the substituent R is either benzyl or a halogen-substituted benzyl. Preferably when R is a halogen-substituted benzyl it is a benzyl substituted by one or more halogens, most preferably by chlorine and/ or bromine.
The compounds which are used according to the present invention are partially known compounds which can be produced by known methods, for example by the reaction of the corresponding substituted benzyl halogenide with the salt (preferably the alkali metal or ammonium salt) of the corresponding carbamic acid, for example the monothiocarbamic acid or the dithiocarb amic acid.
Compounds of the above general formula wherein the States Patent 0 TABLE 1 Compound N 0. X1
ommmmmm It should, however, be noted that compounds which are substituted at the nitrogen atom with other alkyl groups or wherein the benzyl radical is substituted by other halogen-s are also active acaricidal agents.
The acaricidal agents of the present invention have been found to be much more eflfective than O-phenyl esters or S-phenyl esters of carbamic acids or monothiocarbamic acid-s.
The compounds of the present invention may be used in various acaricidal dosages in application thereof to an area subject to spider mites attack in order to combat such spider mites attack, and the range of dosage may vary quite considerably in view of the fact that very low dosages are efiiective, and very high dosages are compatible with continuation of the plant life.
The agents can be applied with any carrier commonly used for agents of this type, and in any form, for example in the form of a suspension, emulsion, powder, solution, aerosol, or the like. The agents may be applied alone or in admixture with other insecticides, fungicides, or the like.
Among the suitable liquid and solid carriers for the compounds of the present invention are water, mineral oils, organic solvents, emulsifying or suspending agents, bentonite, fullers earth, gypsum, lime, diatomaceous earth, pyrophyllite, silica, talc, chalk, or the like. Emulsifiers, wetting agents or binding agents may be added to the preparations as well as carrier gases, odoriferous substances, substances for attracting, or repellants. As indicated the preparations can be in the form of dust, agents for spreading, gnanulates, for spraying, atomizable liquids, aerosols, etc.
The following examples are illustrative of preparations prepared in accordance with the present invention. The scope of the invention is not, however, meant to be limited to the specific details of the examples:
Example 1 PREPARATION OF A WW TABLE POWDER FOR 'SPRAYING A mixture is prepared of:
50% N,N-dimethylthiocarbamic acid benzyl ester 10% lignin sulfonic acid (calcium salt) 5% sodium salt of sulfonated ethylmethyloleylamide 3 urea-formaldehyde condensate 2% starch decomposition product 30% carrier (aluminum silicate) Example 2 PREPARATION OF AN EhIULSION CONCENTRATE A preparation is prepared of: 20% N,N-dimethylthiocarbamic acid benzyl ester 1% of a mixture of oil soluble sulfonates and polyoxyethylene products 89% solvent naphtha The activity of the new acaricidal agents of the present invention is apparent from Table 2 below:
The tests Were carried out in such manner that bush beans which were infested with bean spider mites of all stages of developments (adults-A), (nymphsN), (larvaeL) and (summer eggs-E) were treated with aqueous suspensions of the agents indicated. The acaricidal effect was determined after 1, 3 and 7 days.
The above figures are the result of 15 parallel series of experiments under equal conditions.
The amount of the active substance of the compounds of this invention which are used in the preparations for combatting spider mites may vary in ample limits. It depends on the kind of formulation, the kind of application, the desired measure of control and the kind of the pests to be combatted. Depending on the kind of preparation the amount of active substance in the agent may be about 0.1 to 90 percent by weight. The agents may be applied in concentrations as low as 0.01 percent by weight. Usually good results are received by concentrations between about 0.025 and 10 percent in liquid or solid carriers. For special purposes higher concentrations may be desired for instance as high as about 20 percent.
Without further analysis, the foregoing will so fully reveal the gist of the present invention that others can by applying current knowledge readily adapt it for various applications without omitting features that, from the standpoint of prior art, fairly constitute essential characterisics of the generic or specific aspects of this invention and, therefore, such adaptations should and are intended to be comprehended within the meaning and range of equivalence of the following claims.
What is claimed as new and desired to be secured by Letters Patent is:
1. The method of killing acarids, which comprises contacting the acarids with a compound of the formula:
wherein R is selected from the group consisting of hydrogen and alkyl, wherein R is alkyl, wherein X is selected from the group consisting of oxygen and sulfur, wherein X is selected from the group consisting of oxygen and sulfur, and wherein R is selected from the group consisting of benzyl and halogen-substituted benzyl radicals.
2. The method of combatting spider mites attack, which comprises applying to an area subject to spider mites attack a compound of the formula:
wherein R is selected from the group consisting of hydrogen and alkyl, wherein R is alkyl, wherein X is selected from the group consisting of oxygen and sulfur, wherein X is selected from the group consisting of oxygen and sulfur, and wherein R is selected from the group consisting of benzyl and halogen-substituted benzyl radicals.
3. The method of combatting spider mites attack, which comprises applying to an area subject to spider mites attack a compound of the formula:
N- C-S-R; CH3 0 wherein R is benzyl.
4. The method of combatting spider mites attack, which comprises applying to an area subject to spider mites attack a compound of the formula:
wherein R is p-chlorobenzyl.
5. The method of combatting spider mites attack, which comprises applying to an area subject to spider mites attack a compound of the formula:
wherein R is benzyl.
6. The method of combatting spider mites attack, which comprises applying to an area subject to spider mites attack a compound of the formula:
wherein R is p-chlorobenzyl.
7. The method of combatting spider mites attack, which comprises applying to an area subject to spider mites attack a compolgid of the formula:
Cfiz (H) wherein R is benzyl.
8. The method of combatting spider mites attack, which comprises applying to an area subject to spider mites attack a compound of the formula:
NCSR; CH3 0 wherein R is p-chlorobenzyl.
9. The method of combatting spider mites attack, which comprises applying to an area subject to spider mites attack a compound of the formula:
10. The method of combatting spider mites attack,
which comprises applying to an area subject to spider mites attack a compound of the formula:
NC-ORa CH3 0 wherein R is p-chlorobenzyl.
References Cited in the file of this patent UNITED STATES PATENTS 2,854,374 Huisman Sept. 30, 1958 2,990,319 Jones June 27, 1961 FOREIGN PATENTS 320,209 Switzerland May 15, 1957 692,659 Germany May 30, 1940.

Claims (1)

1. THE METHOD OF KILLING ACARIDS, WHICH COMPRISES CONTACTING THE ACARIDS WITH A COMPOUND OF THE FORMULA:
US102080A 1959-12-28 1960-12-28 Acaricide agent Expired - Lifetime US3098001A (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3265563A (en) * 1961-05-01 1966-08-09 Stauffer Chemical Co Phenyl nu-alkyl thiolcarbamate microbiocide
US3301885A (en) * 1964-04-13 1967-01-31 Velsicol Chemical Corp Phenyl nu-hydrocarboxy nu-hydrocarbyl thiocarbamates
US3340294A (en) * 1965-05-10 1967-09-05 Velsicol Chemical Corp N-substituted and unsubstituted alkyl and alkenyl-2-dimethylamino-benzhydrylcarbamates
US3356713A (en) * 1962-11-14 1967-12-05 Velsicol Chemical Corp p-phenylene-dicarbamates
US3377346A (en) * 1963-06-12 1968-04-09 Sandoz Ltd Novel parasiticides and their production
US3399228A (en) * 1963-04-02 1968-08-27 Union Carbide Corp 3, 4-dichlorobenzyl nu-methylcarbamate herbicide
US3422199A (en) * 1967-05-23 1969-01-14 Velsicol Chemical Corp Acaricidal composition containing n-substituted and unsubstituted alkyl and alkenyl - 2-dimethylamino-benzhydrylcarbamates
US3852167A (en) * 1972-02-08 1974-12-03 Dow Chemical Co Flotation of nickel sulfide ores
US3923854A (en) * 1969-05-08 1975-12-02 Ciba Geigy Ag Derivatives of thiocarbamic acid, their manufacture and their use for combating insects and representatives of the order acarina
US4108885A (en) * 1967-08-25 1978-08-22 Schering Ag Salts of thiocarbamic esters with fungicidal and fungistatic action
WO1983000329A1 (en) * 1981-07-27 1983-02-03 Stauffer Chemical Co S-benzyl thiolcarbamates and their use in controlling weeds in rice fields

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE692659C (en) * 1937-05-21 1940-06-24 I G Farbenindustrie Akt Ges Insect control
CH320209A (en) * 1953-05-16 1957-03-31 Rhone Poulenc Chemicals Use of carbamic esters in insect control
US2854374A (en) * 1953-06-09 1958-09-30 Philips Corp Method of killing insects using chlorophenyl-n,n-dimethylcarbamates
US2990319A (en) * 1955-03-24 1961-06-27 Fmc Corp Synergistic insecticidal compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE692659C (en) * 1937-05-21 1940-06-24 I G Farbenindustrie Akt Ges Insect control
CH320209A (en) * 1953-05-16 1957-03-31 Rhone Poulenc Chemicals Use of carbamic esters in insect control
US2854374A (en) * 1953-06-09 1958-09-30 Philips Corp Method of killing insects using chlorophenyl-n,n-dimethylcarbamates
US2990319A (en) * 1955-03-24 1961-06-27 Fmc Corp Synergistic insecticidal compositions

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3265563A (en) * 1961-05-01 1966-08-09 Stauffer Chemical Co Phenyl nu-alkyl thiolcarbamate microbiocide
US3356713A (en) * 1962-11-14 1967-12-05 Velsicol Chemical Corp p-phenylene-dicarbamates
US3399228A (en) * 1963-04-02 1968-08-27 Union Carbide Corp 3, 4-dichlorobenzyl nu-methylcarbamate herbicide
US3399048A (en) * 1963-04-02 1968-08-27 Union Carbide Corp Substituted benzyl nu-methylcarbamates as herbicides
US3377346A (en) * 1963-06-12 1968-04-09 Sandoz Ltd Novel parasiticides and their production
US3301885A (en) * 1964-04-13 1967-01-31 Velsicol Chemical Corp Phenyl nu-hydrocarboxy nu-hydrocarbyl thiocarbamates
US3340294A (en) * 1965-05-10 1967-09-05 Velsicol Chemical Corp N-substituted and unsubstituted alkyl and alkenyl-2-dimethylamino-benzhydrylcarbamates
US3365484A (en) * 1965-05-10 1968-01-23 Velsicol Chemical Corp Alkyl benzhydrylcarbamates
US3422199A (en) * 1967-05-23 1969-01-14 Velsicol Chemical Corp Acaricidal composition containing n-substituted and unsubstituted alkyl and alkenyl - 2-dimethylamino-benzhydrylcarbamates
US4108885A (en) * 1967-08-25 1978-08-22 Schering Ag Salts of thiocarbamic esters with fungicidal and fungistatic action
US3923854A (en) * 1969-05-08 1975-12-02 Ciba Geigy Ag Derivatives of thiocarbamic acid, their manufacture and their use for combating insects and representatives of the order acarina
US3852167A (en) * 1972-02-08 1974-12-03 Dow Chemical Co Flotation of nickel sulfide ores
WO1983000329A1 (en) * 1981-07-27 1983-02-03 Stauffer Chemical Co S-benzyl thiolcarbamates and their use in controlling weeds in rice fields

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