US3663707A - Molluscicidal oxime carbamates - Google Patents

Molluscicidal oxime carbamates Download PDF

Info

Publication number
US3663707A
US3663707A US1861A US3663707DA US3663707A US 3663707 A US3663707 A US 3663707A US 1861 A US1861 A US 1861A US 3663707D A US3663707D A US 3663707DA US 3663707 A US3663707 A US 3663707A
Authority
US
United States
Prior art keywords
methylcarbamate
acetaldoxime
compounds
carbon atoms
bait
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US1861A
Other languages
English (en)
Inventor
Johannes Th W Montagne
Willem A Van Tongeren
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell USA Inc
Original Assignee
Shell Oil Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Oil Co filed Critical Shell Oil Co
Application granted granted Critical
Publication of US3663707A publication Critical patent/US3663707A/en
Assigned to E.I. DU PONT DE NEMOURS AND COMPANY reassignment E.I. DU PONT DE NEMOURS AND COMPANY ASSIGNS AS OF OCTOBER 1, 1986 THE ENTIRE INTEREST SUBJECT TO AGREEMENTS RECITED (SEE RECORD FOR DETAILS). Assignors: SHELL OIL COMPANY
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

  • This invention relates to the use of certain oxime carbamates as molluscicides.
  • This invention relates to molluscicidal use of certain oxime carbamate compounds.
  • the present invention provides a method of combatting molluscs which comprises applying to a mollusc habitat a molluscicidally effective amount of a composition comprising, as active ingredient, an oxime carbamate of general formula:
  • R is cyanoalkylthio of 1 to 6 carbon atoms, or alkynylthio of up to 6 carbon atoms; R is alkyl of 1 to 6 carbon atoms; R is alkyl of 1-2 carbon atoms.
  • Example's of these compounds include: 1-(5-cyano- :their high activity, are compounds of Formula I wherein R is propynylthio or butynylthio; R is alkyl of l to 3 carbon atoms. Examples of this class of compounds include: l-propargylthio acetaldoxime N-methylcarbamate,
  • the compound most preferred for use in the method of the invention is 1-(2-cyanoethylthio) acetaldoxime N- methylcarbamate.
  • Oximes can exist in two stereoisomeric forms known as syn and anti, and this type of stereoisomerism exists also in the oxime carbamates of the present invention. Both stereoisomeric forms of the oxime carbamates, together with mixtures of the two forms, fall within the scope of the present invention.
  • mollusc are agricultural and horticultural pests.
  • the method of the invention is therefore particularly useful for the protection against attack by such molluscs of crops which are growing or are to be grown in a mollusc habitat.
  • compositions suitable for use in the method of the invention comprise a compound of Formula I and a carrier or a surface-active agent or both a carrier and a surfaceactive agent, and also a food bait for the mollusc.
  • carrier means a material, which may be inorganic or organic and of synthetic or natural origin, with which the active compound is mixed or formulated to facilitate its application to the plant, seed, soil or other object to be treated, or its storage, transport or handling.
  • the carrier may be a solid or a tfluid. Any of the material usually applied in formulating pesticides may be used as as carrier.
  • suitable solid carriers are silicates, clays, for example, kaolinite clay, synthetic hydrated silicon oxides, synthetic calcium silicates, elements such as for example, carbon and sulphur, natural and synthetic resins such as for example, coumarone resins, rosin, copal, shellac, dammar, polyvinyl chloride and styrene polymers and 'copolymers, solid polychlorophenols, bitumen, asphaltite, waxes, such as for example, beeswax, parafliu 'wax, montan wax and chlorinated mineral waxes, and
  • solid fertilizers for example, superphosphates.
  • Suitable fluid carriers are water, alcohols, such as for example, isopropanol, ketones, such as for ex 'ample, acetone, methyl ethyl ketone, methyl isobutyl
  • the surface-active agent may be a wetting agent, an emulsifying agent or a dispersing agent; it may be nonionic or ionic. Any of the surface-active agents usually applied in formulating herbicides or insecticides may be used.
  • suitable surface-active agents are the sodium or calcium salts of polyacrylic acids, the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; partial esters of the above fatty acids with glycerol, sorbitan, sucrose or pentaerythritol; condensation products of alkyl phenols, for example, p-octylphenol or p-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or'sulphonates of these condensation products; and alkali metal salts, preferably sodium salts of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example, sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates such as sodium dodecylbenz
  • compositions of the method of the invention include a food bait for the mollusc, which may also act as carrier for the toxicant.
  • the mollusc food bait may be wheat, corn, barley, maize, rice, bran, groundnut, or any other vegetable product used for animal feeding.
  • One or more of the following substances may be used as a supplement to the mollusc food bait, making the food bait more palatable to the mollusc:
  • B vitamin particularly, B1, B2, B6, nicotinic acid or nicotinamide.
  • an animal or vegetable proteinaceous material for example, albuminoids and their hydrolytic degradative products, particularly those obtained by enzymic hydrolysis, for example, with pepsin, such as a metaproteins, proteoses, peptones, polypeptides, peptides, diketopiperazines and amino carboxylic acids.
  • pepsin such as a metaproteins, proteoses, peptones, polypeptides, peptides, diketopiperazines and amino carboxylic acids.
  • nucleic acid or a hydrolytic degradation product thereof such as a nucleotide, a nucleoside, adenine, guanine, cytosine, uracil or thymine.
  • an ammonium salt for example, ammonium acetate.
  • an amino sugar for example, glucosamine or galactosamine.
  • compositions may be formulated in any of the ways used for formulating pesticides.
  • Particularly suitable formulations are granules or pellets comprising 0.5- 25, preferably 2-10% w. toxic and up to about 50% W. bait attractant.
  • the granules or pellets may be manufac tured by any of the known techniques, for example, by agglomeration, extrusion, compaction or stick-on techniques.
  • Granules are usually prepared to have a size between 10 and 100 BS mesh.
  • the formulations preferably also include 0.l-5% w. preservative, 05-20% W. binding agent and -70% w. slow release modifiers.
  • a preservative into the compositions inhibits the occurrence of fungal and/or bacterial growth on or in the compositions, and thus largely overcomes any problems of deterioration in use or from storage for long periods.
  • Any food preservative known to the art as haivng fungistatic or fungicidal and/or bacterial or bacteriostatic action may be used, for example, sodium benzoate, methyl p-hydroxybenzoate, cetyl trimethyl ammonium bromide, citric acid, tartaric acid, sorbic acid, a phenol, an alkyl phenol or a chlorinated phenol.
  • Suitable binding agents such as alginic acid, alginates, alginate esters, starches, dextrins, cellulose derivatives and glues.
  • Suitable release modifiers include clays, such as bentonite or kaolinite, silicon oxides, polymeric materials such as cellulose, cellulose ethers, particularly cellulose acetate, and resins, for example, urea formaldehyde resins, soya flour, waxes stearates and oils, for example, castor oil.
  • a suitable dye for example, a blue dye, may be also incorporated into the bait granules or pellets to render them unattractive to other forms of wild life, such as birds, and domestic animals.
  • Hal represents a halogen, preferably chlorine, atom and R R R and R have the meanings defined in respect of Formula I.
  • the compounds of the invention are illustrated in the following examples, in which parts by weight (w.) and parts by volume (v.) bear the same relation as the kilogram to the liter.
  • EXAMPLE IV.MOLLUSCICIDAL ACTIVITY The molluscicidal activity of the compounds used in the method of the invention was tested by one or more of the following methods, using as test molluscs, fieldcollccted specimens of the grey field slug Agriolimax reticulams.
  • a 2 /2 bait was prepared by dissolving a fixed weight of the test compound in acetone, mixing this solution with the appropriate amount of milled bran and allowing the acetone to evaporate. 0.5 g. of this bran bait was sprinkled over the surface of a moist filter paper in a Petri-dish and 4. specimens of A. reticulatus wereintroduced and left exposed to the bait for 24 hours. The slugs were then transferred to a clean Petri-dish containing moist filter paper and fresh lettuce and after 48 hours the mortalities were recorded.
  • test (c) The contact activity of certain of the test compounds was assessed by spraying a solution of the toxicant onto a moist mud surface to give a concentration of 2 kg. toxicant/ha. Specimens of A. reticulatus were introduced and exposed to the surface for 24 hours. Recovery was on fresh lettuce as in test (a) above.
  • a method of combatting molluscs which comprises cyanoalkyl of 1 to 4 carbon atoms; and R is alkyl of 1 to applying to said molluscs a molluscicidally effective amount 3 carbon atoms. of an oxime carbamate of the following formulap 4.
  • R is cyanoalkylthio of 1 to 6 carbon atoms or 5 Crown, H Econ Em vol. 60, No. 4 (1967), pp. alkynylthio of up to 6 carbon atoms; R is alkyl of 1 to 1048, 1049 p U V V V 6 carbon atoms; and R is alkyl of 1 to 2 carbonatoms.
  • V 1 Y 2.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US1861A 1969-01-21 1970-01-09 Molluscicidal oxime carbamates Expired - Lifetime US3663707A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3323/69A GB1240622A (en) 1969-01-21 1969-01-21 Molluscicides

Publications (1)

Publication Number Publication Date
US3663707A true US3663707A (en) 1972-05-16

Family

ID=9756155

Family Applications (1)

Application Number Title Priority Date Filing Date
US1861A Expired - Lifetime US3663707A (en) 1969-01-21 1970-01-09 Molluscicidal oxime carbamates

Country Status (5)

Country Link
US (1) US3663707A (enrdf_load_stackoverflow)
CH (1) CH523007A (enrdf_load_stackoverflow)
DE (1) DE2002178A1 (enrdf_load_stackoverflow)
FR (1) FR2028779B1 (enrdf_load_stackoverflow)
GB (1) GB1240622A (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5017620A (en) * 1989-08-10 1991-05-21 E. M. Matson, Jr., Company, Inc. Pesticide composition

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4454134A (en) * 1976-06-14 1984-06-12 Union Carbide Corporation Amide carbamates and amide oxime compounds
LU81543A1 (fr) * 1979-07-23 1981-03-24 Airwick Ag Compositions insecticides systemiques a diffusion controlee
US4640927A (en) * 1984-03-30 1987-02-03 Uniroyal Chemical Company, Inc. Substituted oxime carbamates
US4826685A (en) * 1986-11-17 1989-05-02 Landec Labs, Inc. Molluscicidal device

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1498899A (enrdf_load_stackoverflow) * 1965-11-10 1968-01-10 Shell Nv
FR1467548A (fr) * 1966-01-10 1967-01-27 Du Pont Carbamyl hydroxamates, leur préparation et leur utilisation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5017620A (en) * 1989-08-10 1991-05-21 E. M. Matson, Jr., Company, Inc. Pesticide composition

Also Published As

Publication number Publication date
DE2002178A1 (de) 1970-07-30
FR2028779A1 (enrdf_load_stackoverflow) 1970-10-16
GB1240622A (en) 1971-07-28
FR2028779B1 (enrdf_load_stackoverflow) 1973-10-19
CH523007A (de) 1972-05-31

Similar Documents

Publication Publication Date Title
AU734985B2 (en) Improvement in the effect of herbicides
EP0010588B1 (de) Schwefelhaltige Oxim-Verbindungen und ihre Verwendung zum Schutz von Kulturpflanzen
US3663707A (en) Molluscicidal oxime carbamates
CA1257608A (en) Certain n-phenyl amines and their use as herbicides
US2779669A (en) Acyl pseudourea herbicidal composition and a method for killing weeds therewith
JPH0655708B2 (ja) スルホンアミド系化合物及び農業用殺菌剤
FR2577759A1 (fr) Composition pesticide a base de buprofezine et de carbone actif
KR950004704B1 (ko) 이미노옥사졸리딘 및 그 제조방법
JP3560636B2 (ja) 軟体動物駆除剤
US4210440A (en) Urea derivatives, process for preparing the same and herbicidal composition containing the same
JP2010526843A (ja) カタツムリ用ベイト剤
CS240995B2 (en) Insecticide agent and production method of its effective compound
DE2226301A1 (de) Alkyl-1-(n-substituierte thiocarbamoyl)-2-benzimidazolcarbamate
HU201653B (en) Preparation against mollusks containing 2-92-chloro-1-methoxy-ethoxy)-phenyl-methyl-carbamate and in given case methyl-benzimidazole-2-il-carbamate as agent
EP0617893B1 (en) Molluscicides
KR790001602B1 (ko) 제초제 조성물
US4102673A (en) 1-Phenyl-hexyl ureas as herbicides
EP0175332A2 (en) Herbicide compositions of extended soil life
PL100507B1 (pl) Srodek szkodnikobojczy
JPS5826882B2 (ja) 水面施用用農薬粒剤
CS241095B2 (en) Herbicide
CH663612A5 (de) N-substituierte aminopropansulfonsaeure-derivate.
CA1219864A (en) Pesticidal nitromethane derivatives
KR830001149B1 (ko) 살충 조성물
JPS5827763B2 (ja) 除草剤

Legal Events

Date Code Title Description
AS Assignment

Owner name: E.I. DU PONT DE NEMOURS AND COMPANY

Free format text: ASSIGNS AS OF OCTOBER 1, 1986 THE ENTIRE INTEREST SUBJECT TO AGREEMENTS RECITED;ASSIGNOR:SHELL OIL COMPANY;REEL/FRAME:004676/0234

Effective date: 19860929