US3873298A - Synergistically active herbicidal mixtures for the control of weeds in rice crops - Google Patents

Synergistically active herbicidal mixtures for the control of weeds in rice crops Download PDF

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Publication number
US3873298A
US3873298A US295408A US29540872A US3873298A US 3873298 A US3873298 A US 3873298A US 295408 A US295408 A US 295408A US 29540872 A US29540872 A US 29540872A US 3873298 A US3873298 A US 3873298A
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United States
Prior art keywords
active substance
weeds
formula
triazine
ethylamino
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Expired - Lifetime
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US295408A
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English (en)
Inventor
Hermann Bieringer
Ludwig Ebner
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Novartis Corp
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Ciba Geigy Corp
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Classifications

    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63B—APPARATUS FOR PHYSICAL TRAINING, GYMNASTICS, SWIMMING, CLIMBING, OR FENCING; BALL GAMES; TRAINING EQUIPMENT
    • A63B67/00—Sporting games or accessories therefor, not provided for in groups A63B1/00 - A63B65/00
    • A63B67/10—Games with thread-suspended or swingably-mounted bodies, e.g. balls, pointed bodies shaped as birds, animals, or the like, for aiming at and hitting targets ; Games using tethered bodies, e.g. balls, not otherwise provided for
    • 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
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom

Definitions

  • N-containing ring represents a cyclohexamethyleneimine radical or the 2-methylpiperidyl group, and optionally at least one active substance of formula II S-Cll wherein alkyl denotes a lower alkyl radical containing 2 to 5 carbon atoms, or at least one growth hormone of the phenoxyacetic acid type of formula III O-GH-CO-OR.
  • R represents a chlorine atom or the methyl group, and R represents hydrogen, an alkali atom, or an alkyl radical containing 1 to 8 carbon atoms, preferably l to 4 carbon atoms.
  • the ratio of the mixture componentslzll or 1:1" is 10-11 to 1:3, preferably 6:1 to 2:] parts by weight.
  • Suitable alkyl radicals for the formula II are ethyl, npropyl, isopropyl, n-butyl, isobutyl, sec. butyl, tert. butyl and all eight amyl isomers.
  • alkyl radicals for the formula III there may be cited preferably methyl, ethyl, n-propyl, isopropyl, nbutyl, isobutyl, hexyl, heptyl and isooctyl.
  • 2-methylthio-4-ethylamino-o-isopropylamino-striazine 2-methylthio-4-ethylamino-6-sec.butylamino-striazine, 2-methylthio-4-ethylamino--isobutylamino-striazine, 2-methylthio-4-ethylamino-6-tert.butylamino-striazine, 2-methylthio-4-ethylamino 6-[a
  • Dithiophosphates of formula I are known from the French Pat. No. 1,594,966 or from the Indian Pat. No. 1 18,938 as herbicides.
  • 1,3,5-Triazines of formula II and phenoxyacetic acid derivatives of formula III have been in use for a long time for the regulation of plant growth, particularly as herbicides.
  • synergism in this connection an increased overall effect which exceeds, in the desired direction, the purely cumulative individual effects of the respective components concerned.
  • the term is taken to include also the improvement in the sphere ofaction against weeds, the reduction or elimination of undesirable secondary effects of the active substances with respect either to cultivated plants or to the environment in general, and/or the appearance of favourable new properties not inherent in the individual constituents.
  • the mixtures according to the invention render possible the sustained control of, in particular, the following principal weeds occurring in rice crops:
  • Such carriers or additives can be either solid or liquid and take theform of solvents, diluents, dispersants, wetting agents, adhesives, thickeners or binders.
  • the active substance mixtures are formulated accordingly as emulsion or suspension concentrates, wettable powders, dust, scattering powders, or granules.
  • the sprayable solutions for direct application contain, for example, mineral oil fractions having a high to medium boiling range, particularly a range above 100C, for example diesel oil or kerosene, also coal tar oil or vegetable or animal oils, and also hydrocarbons, for example, alkylated naphthalenes, tetrahydronaphthalene, xylene mixtures, cyclohexanols; and optionally too, moreover, ketones, chlorinated hydrocarbons, such as tetrachloroethane, trichloroethylene or triand tetrachlorobenzenes.
  • mineral oil fractions having a high to medium boiling range particularly a range above 100C
  • hydrocarbons for example, alkylated naphthalenes, tetrahydronaphthalene, xylene mixtures, cyclohexanols
  • ketones, chlorinated hydrocarbons such as tetrachloroethane, trichloroethylene
  • aqueous application forms used are emulsion concentrates, pastes, or wettable powders, with the addition of water.
  • Suitable emulsifying agents or dispersants are non-ionic products, for example, condensation products of aliphatic alcohols, amines or carboxylic acids containing a long chain hydrocarbon radical of about to 30 carbon atoms and ethylene oxide, for example the condensation product of octadecylalcohol and to moles of ethylene oxide, or that of soya fatty acid and 30 moles of ethylene oxide, or that of industrial oleylamine and 15 moles of ethylene oxide, or that of dodecylmercaptan and 12 moles of ethylene oxide.
  • condensation products of ethylene oxide and hydroaromatic polycyclic carboxylic acids or amines may also be used.
  • anionic emulsifying agents that can be used there may be mentioned: the sodium salt of dodecylalcohol sulphuric acid ester, the sodium salt of dodecylbenzenesulphonic aicd, the potassium or triethanolamine salt of oleic acid or abietic acid or of mixtures of these acids, or the sodium salt ofa petroleumsulphonic acid.
  • Suitable cationic dispersants are quaternary ammonium and phosphonium compounds such, for example, as cetylpyridinium chloride or dioxyethylbenzyldodecylammonium chloride.
  • agents according to the invention may contain as solid carriers talcum, kaolin, bentonite, sand, calcium carbonate, calcium phosphate, also charcoal, cork powder, sawdust and other substances of vegetable origin.
  • dusts having a content of 5-10 of the active mixture by diluting a wettable powder with a finely divided solid carrier.
  • Wetting agents and dispersants can also be omitted or replaced by others.
  • the various preparations can contain in conventional manner an admixture of substances that improve the distribution, fixation or penetrability. Examples of such substances are fatty acids, resins, glue, casein or alginates.
  • granules have proved very advantageous in combating weeds in rice, chiefly in water rice.
  • Such granules are manufactured by dissolving the active substance mixture in an oganic solvent and applying the resulting solution to a granulated mineral, for example attapulgite, SiO granicalcium, bentonite and the like, and then evaporating the solvent.
  • polymer granules are prepared by mixing the active substances with polymerisable compounds (urea/formaldehydes, dicyandiamide/ formaldehyde, melamine/formaldehyde or others), whereupon a mild polymerisation is carried out that does not affect the active substances, and the granulation is performed during the gel formation. It is more advantageous to impregnate finished, porous polymer granules (urea/formaldehyde, polyacrylonitrile, polyester or others) which have a specific surface and favourable adsorption/desorption ratio with the active substances, for example in the form of their soutions (in a low boiling solvent) and to remove the solvent.
  • polymerisable compounds urea/formaldehydes, dicyandiamide/ formaldehyde, melamine/formaldehyde or others
  • Polymer granules of this kind can be distributed in the form of microgranules having bulk densities or preferably 300 g/litre to 600 g/litre using atomisers.
  • the dusting can be carried out from aircraft over extensive areas.
  • Additional fertilisers, surface-active agents or sub stances for increasing the specific weight, such as BaSO can of course be added to the granules.
  • the concentration of active substance in herbicidal agents is 0.1- by weight, preferably 5 to 85 by weight.
  • Wettable Powder 1-benzyl-2-stearyl- Emulsion Concentrate a. 40 Parts of an active substance mixture are mixed with 10 parts of a mixture of an anionic surface-active compound, preferably the calcium or magnesium salt of monolauryl-benzene-monosulphonic acid, and a non-ionic surface-active compound, preferably a polyethylene glycol ether of monosorbitol-laureate, and the whole is dissolved in xylene. The solution is made up with xylene to a volume of ml to give a clear solution which can be used as spray concentrate and yields a stable emulsion by pouring it into water.
  • an anionic surface-active compound preferably the calcium or magnesium salt of monolauryl-benzene-monosulphonic acid
  • a non-ionic surface-active compound preferably a polyethylene glycol ether of monosorbitol-laureate
  • Readily soluble active substances can also be formulated as emulsion concentrate according to the following prescription:
  • active substance mixture 70 parts of xylene and 10 parts of a mixture of a reaction product of an alkylphenol and ethylene oxide and calciumdodecylbenzene sulphonate.
  • a sprayable emulsion is obtained by diluting the mixture with water in the desired concentration.
  • Granules a 7.5 Grams of an active substance mixture are dissolved in 100 ml of acetone and the resulting acetonic solution is poured on 92 g of granulated attapulgite (mesh size; 24/28 mesh/inch). The whole is well mixed and the solvent evaporated off in a rotary evaporator.
  • Granules containing 7.5 of active substance. are obtained.
  • Test 3-4-week oil rice plants (height 12-15 cm) reared in a rice field are transplanted in a test field covered with a layer of water to a depth of 3-5 cm.
  • Postemergent After 8-12 days the field with its naturally sprouting weeds is treated once with the active substance or active substance mixture under test.
  • active substance mixtures accordng to the invention achieve not only an additively improved action against weeds, but that primarily at low concentrations they effect an almost total destruction of weeds that occur naturally in rice cultures, for example Echinochloa, Monochoria, Sagit taria, Eleocharis, Cyperus, Rotala, Lindernia, Vandellia and others.
  • Echinochloa, Monochoria, Sagit taria, Eleocharis, Cyperus, Rotala, Lindernia, Vandellia and others.
  • the slight damage caused to the rice culture observed at higher rates of application with pure s-triazine herbicides is, surprisingly, very largely eliminated when these latter are used in admixture with dithiophosphates of the formula I.
  • Testz'For a special test on important weeds in rice crops 3-4-week old rice plants grown in a rice field (height of plants 12-15 cm) are transplanted to an experimental field free from emerged weeds and with a water layer ca. 3-5 cm deep, the most important weeds appearing on this field being Echinochloa crus galli and Eleocharis acicularis.
  • the field, on which has occurred the natural emergence of weeds, is treated once, after 14 days with the active substance or with the active-substance mixture (post-emergent).
  • the mean outside temperature is 30C.
  • Test 3-4-Week old rice plants (height 1215 cm) grown in a rice field were transplanted to a test field having a ca. 3-5 cm deep water layer.
  • the field was treated after 4 days, before emergence of the naturally occurring weeds. with the active substance, or active substance mixture, in the form of a 7.5% granulate (pre-emergent application).
  • a synergistic herbicidal mixture for the control of weeds in rice crops which comprises in an effective amount an active substance of the formula wherein the N-containing ring represents a cyclohexamethyleneimine radical or the 2-methylpiperidyl group together with an active substance of the formula s-ca N If k (k NH-alkyl wherein alkyl represents a C -C alkyl radical; said active substances being present in a weight ratio of from 10:1 to 1:3.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US295408A 1971-10-21 1972-10-05 Synergistically active herbicidal mixtures for the control of weeds in rice crops Expired - Lifetime US3873298A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1533871A CH559506A5 (it) 1971-10-21 1971-10-21

Publications (1)

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US3873298A true US3873298A (en) 1975-03-25

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US295408A Expired - Lifetime US3873298A (en) 1971-10-21 1972-10-05 Synergistically active herbicidal mixtures for the control of weeds in rice crops

Country Status (13)

Country Link
US (1) US3873298A (it)
JP (1) JPS568009B2 (it)
CH (1) CH559506A5 (it)
EG (1) EG10638A (it)
ES (1) ES407797A1 (it)
FR (1) FR2156837B1 (it)
GB (1) GB1353878A (it)
HK (1) HK15877A (it)
IT (1) IT969767B (it)
MY (1) MY7700199A (it)
OA (1) OA04204A (it)
PH (2) PH10083A (it)
SU (2) SU495802A3 (it)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4132542A (en) * 1975-10-22 1979-01-02 Bayer Aktiengesellschaft Organic(thio) phosphoric acid ester compounds and herbicidal compositions
US4137065A (en) * 1972-11-30 1979-01-30 Sumitomo Chemical Company, Ltd. Amido phosphorothiolate pesticide
US4242119A (en) * 1978-02-03 1980-12-30 Ciba-Geigy Corporation Agent for combating sea-water algae
US4838928A (en) * 1985-03-20 1989-06-13 Agan Chemical Manufacturers Ltd. Herbicide

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS52118429A (en) * 1976-03-31 1977-10-04 Sumitomo Chem Co Ltd (di)thiophosphates, their preparation and herbicidal composition containing the same
JPS56128704A (en) * 1980-03-14 1981-10-08 Takeda Chem Ind Ltd Herbicidal composition for rice paddy

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3295947A (en) * 1963-11-26 1967-01-03 Stauffer Chemical Co Herbicidal mixture comprising an s-triazine derivative and nu-(b-omicron, omicron-di-isopropylidithiophosphorylethyl) benzenesulfonamide
US3393991A (en) * 1967-11-07 1968-07-23 Monsanto Co Herbicidal composition and method

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3295947A (en) * 1963-11-26 1967-01-03 Stauffer Chemical Co Herbicidal mixture comprising an s-triazine derivative and nu-(b-omicron, omicron-di-isopropylidithiophosphorylethyl) benzenesulfonamide
US3393991A (en) * 1967-11-07 1968-07-23 Monsanto Co Herbicidal composition and method

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4137065A (en) * 1972-11-30 1979-01-30 Sumitomo Chemical Company, Ltd. Amido phosphorothiolate pesticide
US4132542A (en) * 1975-10-22 1979-01-02 Bayer Aktiengesellschaft Organic(thio) phosphoric acid ester compounds and herbicidal compositions
US4242119A (en) * 1978-02-03 1980-12-30 Ciba-Geigy Corporation Agent for combating sea-water algae
US4260753A (en) * 1978-02-03 1981-04-07 Ciba-Geigy Corporation 2-Methylthio-4-cyclopropylamino-6-(α,β-dimethyl-propylamino)-s-triazine
US4838928A (en) * 1985-03-20 1989-06-13 Agan Chemical Manufacturers Ltd. Herbicide

Also Published As

Publication number Publication date
IT969767B (it) 1974-04-10
GB1353878A (en) 1974-05-22
SU461485A3 (ru) 1975-02-25
ES407797A1 (es) 1975-10-01
JPS4849929A (it) 1973-07-14
OA04204A (fr) 1979-12-31
MY7700199A (en) 1977-12-31
HK15877A (en) 1977-04-15
PH11465A (en) 1978-02-01
CH559506A5 (it) 1975-03-14
PH10083A (en) 1976-08-12
SU495802A3 (ru) 1975-12-15
EG10638A (en) 1976-09-30
JPS568009B2 (it) 1981-02-20
FR2156837A1 (it) 1973-06-01
FR2156837B1 (it) 1977-01-14

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