US2911337A - Method of combating insects comprising contacting with a dichloro-1, 3, 5-triazine - Google Patents

Method of combating insects comprising contacting with a dichloro-1, 3, 5-triazine Download PDF

Info

Publication number
US2911337A
US2911337A US664461A US66446157A US2911337A US 2911337 A US2911337 A US 2911337A US 664461 A US664461 A US 664461A US 66446157 A US66446157 A US 66446157A US 2911337 A US2911337 A US 2911337A
Authority
US
United States
Prior art keywords
triazine
dichlor
compounds
mol
insects
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
US664461A
Other languages
English (en)
Inventor
Uhlenbroek Jan Hendrik
Haeck Hans Heinz
Bijloo Johan Dirk
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.)
US Philips Corp
North American Philips Co Inc
Original Assignee
US Philips Corp
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 US Philips Corp filed Critical US Philips Corp
Application granted granted Critical
Publication of US2911337A publication Critical patent/US2911337A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms

Definitions

  • TWAIClzh-n In this formula Ar designateslan aryl-group, n a number of the value 1 or 2 and x a'number of the value 0, 1, 2, '3
  • phytotoxical' compounds according to the invention have a particular activity against herbaceous. plants, the more strigo'us kinds are also aifected by the said means, but to'a' lesser'ex-tent.
  • Reference rnay furthermore be made to the compounds 2 chloro-'4,6(-diarylamino) l,3, 5-triazine and 2,4-'dichlor-6-arylamino- 1,3,5-tri-azine. These compounds could also be used as fungicides. v
  • This compound is moreover said to havea slight insecticidal activity.
  • the present invention relates to a method of producing means for combating noxious organisms, comprising a derivative of 1,3,S-triazine and is characterized in that a compound of the general formula:
  • X designates NH, -'0- or -S* and R a the group of R had more than 11 carbon atoms.
  • the combating means according to the invention which are derivatives of 2-oxy-4,6-dichlor-l,3,5triazine particularly those are important, in which theflgroup of R contains 3 to'll. carbon atoms.
  • The'active compounds or a mixture thereof can be worked up to obtain combating means in a conventional manner.
  • the active compounds are mixed with solid or liquid carriers or, if necessary, dissolved therein, and, if desired, enriched with dispersion agents,
  • Preparations thus obtained may be'sprayed, pulverized or nebulized in air either as such or emulsified or dispersed in a liquid, for example water.
  • a liquid for example water.
  • mixable oils, spray. powders and atomizing powders These forms are referred to only by way of example and do not intend to restrict the invention.
  • emulsifier In order to produce mixable oils the mixture of active compounds-is dissolved in a suitable solvent, which is immiscible with water, and to this solution is added an emulsifier.
  • suitable solvents are, for example, xylene, toluene dioxane, petroleum distillates rich in aromatic compounds, for example, solvent naphtha, distilled tar oil, furthermore tetraline, cyclohexane or mixtures of these liquids.
  • emulsifiers may beu-sed alkyl phenoxypoly .glycolethers, poly-oxyethylene sorbitane esters of fatty acids or poly oxy-ethylene sorbitol esters of fatty acids.
  • the concentration of the active compounds in the liquidmi-xable with water is not subjected to narrow limits. It may vary,-for example, between 2 and 50% by weight.
  • the mixable oils are emulsified in 'water and this emulsion is sprayed.
  • concentration of active compounds in these aqueous emulsions 1iesbetween0.01 and 0.5% by weight.
  • Thespray powders may be produced by mixing the active compounds with a solid, inert carrier, usually in the presence of a dispersion agent and/ or wetting agent.
  • the spray powders Prior to their use the spray powders are dispersed in liquid, preferably in water and this dispersion is sprayed.
  • any auxiliary substances may in addition be ground.
  • the carrier material may, for example, be alum earth, diatomaceous earth, kaolin, dolomite, talcum, gypsum, chalk, bentonite, attapulgite, infuson'al earth, celite, wood meal, tobacco dust or ground coconut shells.
  • Suitable dispersion agents are lignine sulphonates and naphthalene sulphonates.
  • Wetting agents may be fatty alcohol sulphates, alkyl-aryl-sulphonates or fatty acid condensation products, for example those known under the trade name of Igepon.
  • the concentration of the active compounds is not subjected to narrow limits.
  • the concentration will be chosen to lie between 10 and 80% by weight.
  • Atomizing powders may be produced by applying an active compound or mixtures thereof, as such, or dissolved in a solvent, to a solid carrier. When used, the preparation thus obtained is atomized in the air in a dry, finely pulverulent state.
  • suitable light carriers are employed, also in the manner described for the production of spray powders.
  • the carrier material may be the products referred to above for the production of spray powders.
  • the concentration of active compounds in the atomizing powders is lower than that of the spray powders or mixable oils, but it exceeds the concentration of active compounds in dispersions or emulsions, obtained by diluting spray powders or mixable oils with liquids.
  • the atomizing powders often contain 1 to 20% of active compounds. It may be superfluous to observe that the mixable oils, the spray powders or the atomizing powders according to the invention may be produced by mixing two mixable oils (or spray powders and atomizing powders), each of which contains one of the active compounds.
  • the compounds according to the invention have a comparatively high chlorine content and are capable of splitting ofi hydrochloric acid. 7 This may be undesirable.
  • a compound may be added to the combating substances, which compound is capable of binding the hydrochloric acid set free. To this end use may be made of propylene oxide. A concentration of about 1 to of this compound usually yields satisfactory results.
  • the compounds of the invention are fairly stable, when kept in stock; some of them lose their activity rather soon when they are applied to the soil or mixed therein. Owing to this property these compounds, of which we may mention particularly 2n-butylmercapto-, and 2n-butoxy-, -4,6-dichlor-1,3,5-triazine are particularly suitable to destroy weed like plants from agricultural or horticultural fields before the cultural plants have come up. To this end the compounds may be employed in a quantity of 2 to 20 kgs. per hectare. A quantity of about kgs. per hectare often gives satisfactory results.
  • the phytocidal effect of the compounds of the given formula was determined by tests on tomatoes and garden bean plants in the following manner.
  • a compound to be examined was dissolved in acetone (concentration 1% by weight). Then this liquid was sprayed on a number of tomatoand garden bean-plants in a quantity which corresponded to 10 kgs. of active substance per hectare. A similar test was made with a 3% acetone solution, which was applied to plants in a These powders may be pror quantity which corresponded to 30 kgs. of active substance per hectare. Each series of tests was carried out on two tomato plants and two garden bean plants, the age of which was 3 to 4 weeks. Ten days after the application it was fixed to what extent the plants had suffered from the treatment. The following standard was fixed:
  • triazine -r 100 87 100 100 211-.propyl, mereaptoi, 6-diehlor-l,3,
  • tliazine 100 97 100 100 2n-lsopropy1 mercapto-et, fi-dichlor-l,
  • insecticides according, to the, invention may be dissolved in readily condensable, inert liquids, which are gaseous at room temperature; Assuch use may be made, for example, of fluorine-chlorine-methanes, for instance Freon. If
  • diluents may be added to these solutions, for I example, methylene" chloride. These solutions can be readily nebulized.
  • chloroform tetrachlorcarbon acetone
  • aliphatic ethers for instance diethylether, dimethyl-ether, furthermore aromatic hydrocarbons
  • reaction for instance toluene or benzene. It has been found that inthese solvents the presence of water affects adversely the'yield'of the reaction, so that the reaction is preferably carried, out in an anhydrous medium.
  • an acid binder use may particularly be made of 2,6-alkyl-substituted pyridine, for instances 2,6-dimethyl-' pyridine, 2,4, 6-trimethyl-pyridine, Zmethyl-chinoline, although also other tertiary amines may be used, for instance: dirnethylor diethyl-aniline.
  • the said compounds may, as an alternative, be obtained by causing cyanuric acid chloride to react with a compound of the formula: HXR is an excess quantity in the presence of. an inorganic acid binder, for instance sodium carbonate, sodium bicarbonate or sodium hydroxide. This reaction may be carried out in an aqueous medium.
  • an inorganic acid binder for instance sodium carbonate, sodium bicarbonate or sodium hydroxide.
  • the compounds, wherein X designates O or S-. may furthermore .be produced by reacting cyanuric acid chloride with a compound of the formula: MeX-R, wherein Me designates an alkali atom, for instance sodium ethanolate or-potassium methanolate, or an alkali compound of an aliphatic mercaptane.
  • Me designates an alkali atom, for instance sodium ethanolate or-potassium methanolate, or an alkali compound of an aliphatic mercaptane.
  • This reaction is carried out preferably in the presence of an excess quantity of the alcohol or the mercaptane.
  • other organic solvents for'instance, aliphatic or aromatic others, such as dimethylor diethyl-ether, phenetol anisol; furthermore acetone or benzene and toluene, may be used as diluents.
  • EXAMPLE II.2-ETHOXY-4,6-DICHLOR-1,3,5-TRIAZINE 18.4 g. cyanuric chloride (0.1 mol) was dissolved in 120 mls. of acetone. While being cooled on ice, this solution had added to it in succession, 4.6 g. of ethyl alcohol (0.1 mol) and 13.5 mls. of collidine in a manner such that the temperature of the reaction mixture did not exceed C. The mixture was kept at room temperature for three hours. The hydrochloride acid salt of: collidine formed was then filtered off and washed with acetone. The filtrate was then poured out in ice water.
  • the 2-e'thoxy-4,6-dichlor-1,3,5triazine was precipitated in the form on an oil, which was absorbed in diethyl ether.
  • the ethereal solution was washed four to five times with water, dried on sodium sulphate, filtered and evaporated to dryness. The remaining oil was distilled.
  • the reaction mixture was kept for one hour at a temperature not rising above 0 C. and was then poured out on ice.
  • the 2-methylmercapto-4,6-dichlor-1,3,5 ,-triazine was precipitated in the form of a solid substance; After filtering, washing with water and drying on concentrated sulphuric acid in vacuo, 17.5 g. (89%) of 2- methylmercapto 4,6 dichlor-1,3,5-tn'azine was obtained (melting point 57 to 59 C.). Recrystallisation of the substance from petroleum ether (60 to 80) did not raise the melting point.
  • EXAMPLE XIII.2ETHYLM ERCAPTO-4,6-DICHLOR- 1,3,5-TRIAZINE 18.45 g. (0.1 mol) of cyanuric chloride was dissolved in mls. of acetone. While being cooled on ice, 10 g. (0.16 mol) of ethyl-mercaptan was added, then 13.5 mls. of collidine. During the reaction the mixture was cooled with ice. The reaction was continued for three hours at a temperature between 20 to 25 C. Then the deposit of the hydrochloride acid salt of collidine was filtered ofif, washed out with acetone.
  • EXAMPLE XIV.-2N PROPYLMERCAPTO-4,6-DICHLOB- 1,3,5-TRIAZINE In the same manner as described in Examples X11 and )QII 18.45 g. (0.1 mol) of cyanuric chloride, 8 g. of n-propylmercaptane (0.105 mol) and 13.5 mls. of collidine yielded 20.65 g. (92%) of 2n-propylmercapto-4,6-
  • EXAMPLE XXI A mixable oil was produced by dissolving 25 g. of Znbutylmercapto-4,6-dichlor-1,3,S-triazine in 65 g. of xylene and by adding thereto g. of an emulsifier of the type alkylphenoxy-polyglycol ether (Triton) and 5 g. of propylene oxide the latter substance serving to bind any free hydrochloride acid.
  • Similar mixable oils were produced of 2-isopropylamino-4,6 dichlor-1,3,5-triazine from 2n butoxy-4,6-dichlor-1,3,5-triazine and of 2-allyloxy- 4,6-dichlor-1,3,5-triazine.
  • these mixable oils were diluted with water in a weight ratio varying between 1:200 and 1:40.
  • the aqueous emulsions were used as weed-killing means in a quantity of about kgs. per hectare.
  • EXAMPLE XXII An aerosol was produced by dissolving 0.5 g. of Znbutyl mercapto-4,6-dichlor-1,3,5 triazine in a mixture of 5 g. of xylene, 1 g. of propylene oxide, 40 g. of methylene chloride, 53.5 g. of a fluorine-chlorine-methane compound (a mixture of equal quantities of Freon-11 and Freon-12).
  • a similar aerosol was produced, which contained the same quantity of 2-(3-methylbutyl)mercapto-4,6-dichlor-l,3,5 triazine and 2-butoxy-4,6-dichlor- 1,3,5-triazine.
  • the aerosols were used for combating insects.
  • a method of destroying insects comprising:contact; ing said insects with:an insecticidal.composition containing in: an. insecticidally effectivezamount a. compoundworrer spendingto thegeneral formula.
  • X' designates a member of the groupconsiStingof --O-- and -S- and R designates a member ofthe group consisting of saturated aliphatic hydrocarbon radicals containing from 1 to 11 carbon atoms, the allyl radical and the cyclohexyl radical.
  • a method of destroying insects comprising contacting said insects with an insecticidal composition containing in an insecticidally eifective amount a compoundcorresponding to the general formula:
  • X designates S and R designates a member of the group consisting of saturated aliphatic hydrocarbon radicals containing from 1 to 11 carbon atoms, the allyl radical and the cyclohexyl radical.
  • X designates a member of the group consisting of --O and S and R designates a member of the group consisting of saturated aliphatic hydrocarbon radicals containing from 1 to 11 carbon atoms, the allyl radical and the cyclohexyl radical and a solid carrier therefor.
  • a method of destroying insects comprising contacting said insects with an insecticidal composition containing 2(n alkylmercapto)-4,6-dichloro-1,3,5-triazine in an insecticidally effective amount.
  • a method of destroying insects comprising contacting said insects with an insecticidal composition containing ,2(n-propoxy)-4,6-dichloro-1,3,5-triazine in an insecticidally eflective amount.
  • a method of destroying insects comprising contacting said insects with an insecticidal composition contain ing 2(cyclohexyD-4,6-dichloro-1,3,5-triazine in an insecticidally eflective amount.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US664461A 1956-06-15 1957-06-10 Method of combating insects comprising contacting with a dichloro-1, 3, 5-triazine Expired - Lifetime US2911337A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL359563X 1956-06-15

Publications (1)

Publication Number Publication Date
US2911337A true US2911337A (en) 1959-11-03

Family

ID=19785348

Family Applications (1)

Application Number Title Priority Date Filing Date
US664461A Expired - Lifetime US2911337A (en) 1956-06-15 1957-06-10 Method of combating insects comprising contacting with a dichloro-1, 3, 5-triazine

Country Status (7)

Country Link
US (1) US2911337A (enrdf_load_stackoverflow)
BE (1) BE558354A (enrdf_load_stackoverflow)
CH (1) CH359563A (enrdf_load_stackoverflow)
DE (1) DE1125226B (enrdf_load_stackoverflow)
FR (1) FR1176716A (enrdf_load_stackoverflow)
GB (1) GB818437A (enrdf_load_stackoverflow)
NL (1) NL208063A (enrdf_load_stackoverflow)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3040045A (en) * 1959-10-12 1962-06-19 American Cyanamid Co New process for the preparation of a yellow triazine vat dye
US3134775A (en) * 1957-10-25 1964-05-26 Ici Ltd New pesticidal triazine derivatives
US3169904A (en) * 1957-10-25 1965-02-16 Ici Ltd Triazine derivatives possessing aphicidal properties
US3316264A (en) * 1962-09-13 1967-04-25 Velsicol Chemical Corp 2-phenylthio-4-alkoxy-6-halo-s-triazines
FR2441619A1 (fr) * 1978-11-20 1980-06-13 Degussa Procede pour la fabrication de 2-alcoxyl-4,6-dichloro-s-triazines
US4259487A (en) * 1978-11-20 1981-03-31 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of optionally substituted 2-mercapto-4,6-di-chloro-s-triazines
JP2000063366A (ja) * 1998-04-09 2000-02-29 Ciba Specialty Chem Holding Inc ジレゾルシニル―アルコキシ―および―アリ―ルオキシ―ｓ―トリアジン
US20080207876A1 (en) * 2005-06-10 2008-08-28 Prometic Biosciences Limited Triazines and Pyrimidines as Protein Binding Ligands
CN105949349A (zh) * 2016-05-11 2016-09-21 南京晓庄学院 一种壳聚糖基超分散剂及其制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2510564A (en) * 1946-10-02 1950-06-06 American Cyanamid Co Triallyl cyanurate and insecticidal compositions containing the same
US2513264A (en) * 1950-06-27 Triasine derivatives and methods of
US2537816A (en) * 1951-01-09 Method-of preparing tjnsaturated
US2693408A (en) * 1952-12-08 1954-11-02 Monsanto Chemicals Herbicidal compositions
US2701759A (en) * 1952-01-16 1955-02-08 Us Rubber Co Herbicidal compositions
US2720480A (en) * 1953-07-17 1955-10-11 Ethyl Corp Fungicidal compositions and method of using same
US2773871A (en) * 1953-08-20 1956-12-11 Ciba Ltd Dyestuffs of the anthraquinone series

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE910651C (de) * 1938-02-15 1954-05-03 Dehydag Gmbh Verfahren zur Herstellung von Kondensationsprodukten

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2513264A (en) * 1950-06-27 Triasine derivatives and methods of
US2537816A (en) * 1951-01-09 Method-of preparing tjnsaturated
US2510564A (en) * 1946-10-02 1950-06-06 American Cyanamid Co Triallyl cyanurate and insecticidal compositions containing the same
US2701759A (en) * 1952-01-16 1955-02-08 Us Rubber Co Herbicidal compositions
US2693408A (en) * 1952-12-08 1954-11-02 Monsanto Chemicals Herbicidal compositions
US2720480A (en) * 1953-07-17 1955-10-11 Ethyl Corp Fungicidal compositions and method of using same
US2773871A (en) * 1953-08-20 1956-12-11 Ciba Ltd Dyestuffs of the anthraquinone series

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3134775A (en) * 1957-10-25 1964-05-26 Ici Ltd New pesticidal triazine derivatives
US3169904A (en) * 1957-10-25 1965-02-16 Ici Ltd Triazine derivatives possessing aphicidal properties
US3169964A (en) * 1957-10-25 1965-02-16 Ici Ltd Triazine derivatives possessing aphicidal properties
US3040045A (en) * 1959-10-12 1962-06-19 American Cyanamid Co New process for the preparation of a yellow triazine vat dye
US3316264A (en) * 1962-09-13 1967-04-25 Velsicol Chemical Corp 2-phenylthio-4-alkoxy-6-halo-s-triazines
FR2441619A1 (fr) * 1978-11-20 1980-06-13 Degussa Procede pour la fabrication de 2-alcoxyl-4,6-dichloro-s-triazines
US4259487A (en) * 1978-11-20 1981-03-31 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of optionally substituted 2-mercapto-4,6-di-chloro-s-triazines
US4271299A (en) * 1978-11-20 1981-06-02 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of 2-alkoxy-4,6-dichloro-s-triazines
JP2000063366A (ja) * 1998-04-09 2000-02-29 Ciba Specialty Chem Holding Inc ジレゾルシニル―アルコキシ―および―アリ―ルオキシ―ｓ―トリアジン
US20080207876A1 (en) * 2005-06-10 2008-08-28 Prometic Biosciences Limited Triazines and Pyrimidines as Protein Binding Ligands
US8501939B2 (en) * 2005-06-10 2013-08-06 Prometic Biosciences Limited Triazines and pyrimidines as protein binding ligands
CN105949349A (zh) * 2016-05-11 2016-09-21 南京晓庄学院 一种壳聚糖基超分散剂及其制备方法

Also Published As

Publication number Publication date
BE558354A (enrdf_load_stackoverflow)
GB818437A (en) 1959-08-19
NL208063A (enrdf_load_stackoverflow)
DE1125226B (de) 1962-03-08
CH359563A (de) 1962-01-15
FR1176716A (fr) 1959-04-15

Similar Documents

Publication Publication Date Title
US3234255A (en) Alpha-substituted benzaldoximes
US2909420A (en) Compositions and methods for influencing the growth of plants
US3484455A (en) 2-imino-1,3-dithietanes and processes for their preparation
US2909421A (en) Compositions and methods for influencing the growth of plants
US2911337A (en) Method of combating insects comprising contacting with a dichloro-1, 3, 5-triazine
DE2254200C2 (de) Tetrahydro-1,3,5-triazin-2,6-dione, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide
US2936227A (en) Method for inhibiting the growth of plants
US2996505A (en) Process for the production of triazine thiocyanates
US3753986A (en) Triazine herbicides
EP0056969A2 (de) Substituierte Phenylsulfonylharnstoff-Derivate, Verfahren und neue Zwischenprodukte zu deren Herstellung sowie diese Derivate als Wirkstoffe enthaltende herbizide Mittel
DE1914014A1 (de) Neue 2-Alkylthio-4,6-diamino-S-triazine
AT334134B (de) Bekampfung von pilzschadlingen
CH574214A5 (enrdf_load_stackoverflow)
US3306725A (en) Method for controlling annual weeds in tomato fields
DE2258243A1 (de) Heterocyclische verbindungen und deren verwendung
US3786053A (en) Propionamido triazine
US2864741A (en) Di (alkylmercapto) substituted vinyl, dialkyl phosphate and thiophosphate insecticides
US2887432A (en) Dialkoxyphosphinothioylthio-s-triazines
EP0153601B1 (de) 2-Alkoxyaminosulfonylbenzolsulfonyl-harnstoff-Derivate
US3326913A (en) Azido triazines
US2909419A (en) Compositions and methods for influenc-
DD231725A5 (de) Herbizide mittel
DD139788A5 (de) Pflanzenwuchsregulierende mittel
US3488181A (en) Diamino-s-triazine herbicides
US2944933A (en) Thiophosphoric acid ester