US20020123428A1 - Herbicidal compositions - Google Patents

Herbicidal compositions Download PDF

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Publication number
US20020123428A1
US20020123428A1 US09/353,230 US35323099A US2002123428A1 US 20020123428 A1 US20020123428 A1 US 20020123428A1 US 35323099 A US35323099 A US 35323099A US 2002123428 A1 US2002123428 A1 US 2002123428A1
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Prior art keywords
herbicides
plants
esters
rice
group
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Abandoned
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US09/353,230
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Inventor
Dr. Erwin Hacker
Dr. Hermann Bieringer
Dr. Thomas Auler
Alvaro Melendez
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Bayer CropScience AG
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Hoechst Schering Agrevo GmbH
Aventis CropScience GmbH
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Priority claimed from DE19832017A external-priority patent/DE19832017A1/de
Priority claimed from DE1999128387 external-priority patent/DE19928387A1/de
Application filed by Hoechst Schering Agrevo GmbH, Aventis CropScience GmbH filed Critical Hoechst Schering Agrevo GmbH
Assigned to HOECSHT SCHERING AGREVO GMBH reassignment HOECSHT SCHERING AGREVO GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AULER, THOMAS, BIERINGER, HERMANN, MELENDEZ, ALVARO, HACKER, ERWIN
Publication of US20020123428A1 publication Critical patent/US20020123428A1/en
Priority to US10/241,972 priority Critical patent/US8357629B2/en
Priority to US13/722,689 priority patent/US8791050B2/en
Priority to US13/722,630 priority patent/US8765638B2/en
Assigned to AVENTIS CROPSCIENCE GMBH reassignment AVENTIS CROPSCIENCE GMBH CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: HOECHST SCHERING AGREVO GMBH
Abandoned legal-status Critical Current

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • A01N37/22—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 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • 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
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Definitions

  • the invention is in the field of crop protection compositions which can be used against harmful plants in crops, preferably in rice, and which comprise, as herbicidally active compounds, a combination of at least two herbicides, one herbicide component being selected from the group consisting of the herbicides of the type of the fatty acid biosynthesis inhibitors.
  • a number of compounds from the structure class of the aryloxyphenoxypropionic acids, cyclohexanediones and derivatives of the abovementioned compounds and their derivatives are known as herbicides of the type of the fatty acid biosynthesis inhibitors.
  • An advantage of these compounds is their activity against grasses, and a selective use, if appropriate in combination with safeners, is possible and utilized even in monocotyledonous crops.
  • the effectiveness of these herbicides against harmful plants in the crops is at a high level; however, it depends in general on the application rate, the respective formulation, the harmful plants to be controlled in each case or the spectrum of harmful plants, the climatic and soil conditions, etc.
  • a further criterion is the duration of the action, or the rate of degradation of the herbicide.
  • Also to be taken into account are, if appropriate, changes in the susceptibility of harmful plants toward an active compound which may occur on prolonged use or in geographical locations. Activity losses in individual plants can only be compensated to a certain extent by higher application rates of the herbicides, for example because this frequently decreases the selectivity of the herbicides, or an improvement in activity is not observed, even at higher application rates.
  • a lower application rate reduces not only the amount of an active compound which is required for the application, but generally also reduces the amount of formulation auxiliaries required. Both reduce the economic expense and improve the ecological compatibility of the herbicide treatment.
  • a method for improving the property profile of a herbicide may consist in the combination of the active compound with one or more other active compounds which contribute the desired additional properties.
  • the invention accordingly provides herbicide combinations having an effective content of components (A) and (B), where
  • (A) is one or more herbicides selected from the group consisting of heteroaryloxy- and aryloxy-phenoxypropionic acids, their salts and esters and cyclohexanediones, and
  • (B) is one or more herbicides which are structurally different from the herbicides (A) contained in each case, selected from the group of the compounds consisting of
  • the herbicide combinations according to the invention may contain other components, for example other herbicides, insecticides, fungicides, acaricides, crop protection agents of a different type (for example safeners), plant growth regulators and/or additives and/or formulation auxiliaries which are customary in crop protection.
  • the components can be formulated jointly (ready-to-use formulation) and used, or they can be formulated separately and used jointly, for example in the tank mix or in sequential application.
  • the synergistic effects are observed when the active compounds (A) and (B) are applied jointly; however, they can also frequently be observed when the active compounds are applied at different times (splitting). It is also possible to apply the herbicides or the herbicide combinations in a plurality of portions (sequential application), for example after pre-emergence applications, followed by post-emergence applications or after early post-emergence applications, followed by medium or late post-emergence applications. Preference is given here to the joint or almost simultaneous application of the active compounds of the combination in question, if appropriate in a plurality of portions. However, it is also possible to apply the individual active compounds of a combination at different times, which may be advantageous in the individual case. It is also possible to integrate other crop protection agents, such as fungicides, insecticides, acaricides, etc., and/or various auxiliaries, adjuvants and/or fertilizer applications, into this system application.
  • other crop protection agents such as fungicides, insecticides, acaricides, etc., and/or various aux
  • Suitable combination partners (A) are, for example, the compounds (A1) and (A2) below, which can in each case be employed on their own or in combination with one another (in most cases, the herbicides are referred to by the common name for the active compound, in accordance with the reference “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997, abbreviated “PM”):
  • the application rates of the herbicides (A) are known in principle and are, for the herbicides of type (A1), in the range from 5 g to 500 g of active substance per hectare and, for the herbicides of type (A2), in the range from 10 g to 1000 g of active substance per hectare.
  • the mixtures according to the invention require lower application rates of the particular active compound, compared to the individual application.
  • Suitable combination partners (B) are, for example, the following compounds of the subgroups (B1) to (B4) which are different from the compounds (A) (the herbicides are in most cases referred to by the common name, in accordance with the reference “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997, abbreviated “PM”):
  • Herbicides which are selective in rice, in particular against monocotyledonous harmful plants are, for example, one or more compounds selected from the group consisting of
  • herbicide combinations (A)+(B1) which comprise the following active compounds:
  • the preferred compound (A1.1) is fenoxaprop-P-ethyl.
  • the abovementioned active compounds (B1.1) to (B1.8) are anilides or chloroacetanilides which are active mainly against harmful grasses, for example annual grasses, and can be used in rice. Additionally, butachlor and pretilachlor also cover some broad-leaved weeds in rice, naproanilide, propanil and etobenzanide have as activity spectrum, in addition to grass-like species such as Echinochloa spp., Digitaria spp., Setaria spp., Panicum spp., also broad-leaved weeds, such as Amaranthus spp.
  • the compounds (B1.9) to (B1.12) are thiocarbamates, with the emphasis on the use against Echinochloa spp. in rice.
  • the compound (B1.13) belongs to the chemical class of the quinolinecarboxylic acids and is preferably used against weed grasses such as Echinochloa spp. and other weeds in rice.
  • the compound (B1.14) is a benzoylcyclohexanedione which can be used not only against weed grasses, but also against a broader spectrum of weeds in rice.
  • the compound (B1.17) from the tetrazole series is particularly suitable for controlling weed grasses in rice.
  • the compounds (B1.16) and (B1.22) are organophosphorus compounds and are particularly suitable for controlling annual grasses and seeds in rice.
  • the compound (B1.17) from the group of the ureas is suitable for controlling annual and perennial weed grasses in rice.
  • the compound (B1.18) from the pyridine series is suitable for use against annual grasses in rice.
  • the compound (B1.19) is particularly effective against weed grasses, sedges and some broad-leaved weeds in rice.
  • the compound (B1.20) is employed for controlling important weed grasses in rice.
  • the compound (B1.21) is a grass herbicide against annual harmful plants in rice by the pre- and post-emergence method.
  • the compound (B1.22) is a grass herbicide against annual grasses and also sedges in transplanted rice by the pre- and postemergence method.
  • Herbicides which are selective in rice, mainly against dicotyledonous harmful plants and cyperaceae are, for example, one or more compounds selected from the group consisting of
  • (B2.2) carfentrazone and its esters, such as carfentrazone-ethyl (PM, pp. 191-193) ( (RS)-2-chloro-3-[2-chloro-5-(4-difluoromethyl4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]propionic acid and its esters, such as the ethyl ester),
  • herbicide combinations (A)+(B2) which comprise the following active compounds:
  • Herbicides which are selective in rice, mainly against cyperaceae are, for example, one or more compounds selected from the group consisting of
  • herbicide combinations (A)+(B3) which comprise the following active compounds:
  • Herbicides which are selective in rice, mainly against monocotyledonous and dicotyledonous harmful plants and cyperaceae are, for example, one or more compounds selected from the group consisting of
  • herbicide combinations (A)+(B4) which comprise the following active compounds:
  • salts include those which are formed by exchanging a hydrogen atom at the sulfonamide group for a cation.
  • Compounds (B) are preferably employed:
  • (B1) in amounts of from 10 to 4000, in particular 50-1000 g of AS/ha,
  • (B2.11) in amounts of from 1 to 2000, in particular 5 to 1000 g of AS/ha;
  • ratios (A):(B) are, depending on the effective application rates, generally in the range from 1:200 to 200:1, preferably from 1:100 to 100:1, in particular in the range from 1:50 to 50:1.
  • combinations according to the invention can be employed together with other active compounds, for example from the group of the safeners, fungicides, insecticides and plant growth regulators, or from the group of the additives and formulation auxiliaries which are customary in crop protection.
  • Additives are, for example, fertilizers and colorants. Of particular importance here are those combinations to which one or more other active compounds of a different structure or safeners [active compounds (C)] are added, for example according to the scheme:
  • the active compounds (A) are suitable for controlling the weed spectrum in rice crops, for example of transplanted or sown rice. Moreover, they can, if appropriate, be employed for controlling harmful plants in other crops, for example in economically important crops, such as cereals (wheat, barley, rye, maize), sugarbeet, sugar cane, rapeseed, cotton and soybeans.
  • cereals wheat, barley, rye, maize
  • sugarbeet sugar cane
  • rapeseed cotton and soybeans.
  • the active compounds (A) and (B) it is advantageous, depending on the crop, to apply a safener above certain application rates to reduce or avoid damage to the crop plant.
  • the following groups of compounds are, for example, suitable as safeners for the abovementioned herbicidally active compounds (A):
  • esters 2,4-dichlorophenoxyacetic acid
  • Mecoprop 4-chloro-2-methylphenoxypropionic esters
  • MCPA 3,6-dichloro-2-methoxybenzoic acid
  • safeners are in many cases also suitable for active compounds of group (B). Moreover, the following safeners are suitable for the herbicide combinations according to the invention in rice and other cereal crops, such as, for example, wheat, maize, millet, etc.:
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine from Stauffer
  • PPG-1292 N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide from PPG Industries
  • DK-24 N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide from Sagro-Chem
  • naphthalenedicarboxylic acid derivatives whch are known as seed dressings, such as, for example,
  • CSB (1-bromo4-(chloromethylsulfonyl)benzene) (CAS-Reg. No. 54091-064 from Kumiai), which is known as safener against damage by some herbicides in rice.
  • the invention furthermore provides the following specific two-compound and multi-compound combinations with herbicides and/or safeners:
  • the combinations according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants, as encountered, preferably, in crops of rice.
  • the active compounds also act efficiently on perennial weeds which produce shoots from rhizomes, root stocks or other perennial organs and which are difficult to control.
  • the active compounds act efficiently against, for example, Echinochloa spp., Brachiaria spp., Leptochloa spp. and Digitaria spp., but also against Panicum spp., Agropyron spp., wild cereal forms and Sorghum spp., Setaria spp., Alopecurus spp., Avena spp., Apera spica venti, Lolium spp., Phalaris spp. Cynodon spp., Poa spp. and Cyperus species and Imperata.
  • the spectrum of action extends to species such as, for example, Amaranthus spp., Sphenoclea spp., Heteranthera spp., Eleocharis spp., Ipomoea spp., Eschynomena spp., Sesbania spp.
  • Cyperrus spp. but also Polygonum spp., Xanthium spp., Equisetum, Chenopodium spp., Abutilon spp., Anthemis spp., Lamium spp., Matricaria spp., Stellaria spp., Kochia spp., Viola spp., Datura spp., Chrysanthemum spp., Thlaspi spp., Pharbitis spp., Sida spp., Sinapis spp., Cupsella spp., Ambrosia spp., Galium spp., Emex spp., Lamium spp., Papaver spp., Solanum spp., Cirsium spp., Veronica spp., Convolvulus spp., Rumex and Artemisia.
  • the compounds according to the invention are applied to the soil surface prior to germination, then the weed seedlings are either prevented completely from emerging, or the weeds grow until they have reached the cotyledon stage but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely.
  • the herbicidal compositions according to the invention have a rapid and long-lasting herbicidal action.
  • the shower resistance of the active compounds in the combinations according to the invention is generally favorable. It is a particular advantage that the effective dosages of compounds (A) and (B) used in the combinations can be adjusted to such a low level, that their soil action is optimally low. Thus, it is not only possible to use them in sensitive crops, but groundwater contaminations are virtually avoided.
  • the active compound combination according to the invention it is possible to reduce the required application rate of the active compounds considerably.
  • the compounds according to the invention have an excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, the crop plants are not damaged at all, or only to a negligible extent.
  • the substances according to the invention have outstanding growth-regulating properties in crop plants. They engage in the plant metabolism in a regulating manner and can thus be employed for the targeted control of plant constituents and for facilitating harvesting, for example by provoking desiccation and stunted growth. Furthermore, they are also suitable for generally regulating and inhibiting undesirable vegetative growth, without destroying the plants in the process. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops because lodging can be reduced hereby, or prevented completely.
  • the compounds can be employed for controlling harmful plants in known crops or in still to be developed tolerant or genetically engineered plants.
  • the transgenic plants generally have particularly advantageous properties, in addition to resistance to the substances according to the invention, for example resistance to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other particular properties relate, for example, to the quantity, quality, storage-stability, composition and to specific ingredients of the harvested product.
  • transgenic plants having an increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested product are known.
  • novel plants having modified properties can be generated with the aid of genetic engineering methods (see, for example, EP-A 0 221 044, EP-A 0 131 624). For example, there have been described several cases of
  • transgenic crop plants which are resistant to other herbicides, for example sulfonylureas (EP-A 0 257 993, US-A 5013659),
  • transgenic crop plants having the ability to produce Bacillus thuringiensis toxins (Bt toxins) which impart resistance to certain pests to the plants (EP-A 0 142 924, EP-A 0 193 259),
  • transgenic crop plants having a modified fatty acid composition (WO 91/13972).
  • Plant cells having a reduced activity of a gene product can be prepared, for example, by expressing at least one appropriate antisense-RNA, a sense-RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.
  • DNA molecules which comprise the entire coding sequence of a gene product including any flanking sequences that may be present and DNA molecules which comprise only parts of the coding sequence, it being necessary for these parts to be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but which are not entirely identical.
  • the synthesized protein can be localized in any desired compartment of the plant cells.
  • sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J.1 (1991), 95-106).
  • the transgenic plant cells can be regenerated to whole plants using known techniques.
  • the invention therefore also provides a method for controlling undesirable vegetation, preferably in crops, which comprises applying one or more herbicides of type (A) with one or more herbicides of type (B) onto the harmful plants, parts thereof or onto the area under cultivation.
  • the invention also provides the use of the novel combinations of compounds (A)+(B) for controlling harmful plants, preferably in crops.
  • the active compound combinations according to the invention can be present both as mixed formulations of the two components, if appropriate with other active compounds, additives and/or customary formulation auxiliaries, which are then applied in a customary manner diluted with water, or be prepared as so-called tank mixes by joint dilution of the separately formulated or partially separately formulated components with water.
  • the compounds (A) and (B) or their combinations can be formulated in various ways depending on the prevailing biological and/or chemico-physical parameters.
  • suitable formulation options are: wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL) emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, oil- or water-based dispersions, suspoemulsions, dusts (DP), seed-dressing compositions, granules for broadcasting and soil application, or water-dispersible granules (WG), ULV formulations, microcapsuies or waxes.
  • Wettable powders are preparations which are uniformly dispersible in water and which contain, in addition to the active compound and as well as a diluent or inert substance, surfactants of ionic or nonionic type (wetting agents, dispersants), for example polyethoxylated alkyl phenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalene-sulfonate or else sodium oleoylmethyltaurinate.
  • surfactants of ionic or nonionic type wetting agents, dispersants
  • Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatic compounds or hydrocarbons with the addition of one or more surfactants of ionic or nonionic type (emulsifiers).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatic compounds or hydrocarbons.
  • emulsifiers which can be used are calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitan esters.
  • calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorb
  • Dusts are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or by applying active-compound concentrates to the surface of carriers such as sand, kaolinites or granulated inert material, by means of adhesive binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils.
  • Suitable active compounds can also be granulated in the manner which is customary for the preparation of fertilizer granules, if desired as a mixture with fertilizers.
  • Water-dispersible granules are generally prepared by processes such as spray-drying, fluidized-bed granulation, disk granulation, mixing using high-speed mixers, and extrusion without solid inert material.
  • the agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 2 to 95% by weight, of active compounds of types A and/or B, the following concentrations being customary, depending on the type of formulations:
  • the concentration of active compound is, for example, from about 10 to 95% by weight, the remainder to 100% by weight consisting of customary formulation constituents.
  • concentration of active compound can be, for example, from 5 to 80% by weight.
  • Formulations in the form of dusts usually contain from 5 to 20% by weight of active compound, while sprayable solutions contain from about 0.2 to 25% by weight of active compound.
  • the content of active compound depends partly on whether the active compound is in liquid or solid form and on the granulation auxiliaries and fillers that are used. In water-dispersible granules the content is generally between 10 and 90% by weight.
  • said formulations of active compound may comprise the tackifiers wetting agents, dispersants, emulsifiers, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, antifoams, evaporation inhibitors and pH and viscosity regulators which are customary in each case.
  • the formulations which are in commercially available form, are, if appropriate, diluted in a customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, soil granules, granules for spreading and sprayable solutions are conventionally not diluted any further with other inert substances prior to use.
  • the active compounds can be applied to the plants, parts of the plants, seeds of the plants or the area under cultivation (tilled soil), preferably to the green plants and parts of the plants and, if desired, additionally to the tilled soil.
  • a possible use is the joint application of the active compounds in the form of tank mixes, where the concentrated formulations of the individual active substances, in the form of their optimal formulations, are mixed jointly with water in the tank, and the spray mixture obtained is applied.
  • a joint herbicidal formulation of the combination according to the invention of the active compounds (A) and (B) has the advantage that it can be applied more easily because the amounts of the components have already been adjusted to one another in the correct ratio. Moreover, the auxiliaries of the formulation can be selected to suit each other in the best possible way, while a tank mix of various formulations may result in undesirable combinations of auxiliaries.
  • a dust is obtained by mixing 10 parts by weight of an active compound/active compound mixture and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of an active compound/active compound mixture, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active compound/active compound mixture with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example approximately 255 to 277° C.) and grinding the mixture in a ball mill to a fineness of below 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of an active compound/active compound mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • compositions according to the invention have good herbicidal pre-emergence activity against a broad spectrum of weed grasses and broad-leaved weeds.
  • A, B activity of the active compounds A or B in % at a or b g of AS/ha; E expected value in % at a+b g of AS/ha.
  • compositions according to the invention are placed in sandy loam soil in pots, covered with soil and grown in a greenhouse under good growth conditions (temperature, atmospheric humidity, water supply). Three weeks after sowing, the test plants are treated at the three-leaf stage with the compositions according to the invention.
  • the compositions according to the invention formulated as wettable powders or as emulsion concentrates, are sprayed, at various dosages, onto the green parts of the plant at an application rate of 600 to 800 l of water/ha (converted). After the test plants have been in the greenhouse for about 3 to 4 weeks under ideal growth conditions, the effect of the preparations is scored visually by comparison with untreated controls.
  • the compositions according to the invention also have a good herbicidal post-emergence activity against a broad spectrum of economically important weed grasses and weeds.
  • Crop plants were grown outdoors on plots under natural outdoor conditions, and seeds or rhizome pieces of typical harmful plants were laid out or the natural weed growth was utilized. Treatment with the compositions according to the invention was carried out after the harmful plants had emerged and the crop plants were, generally, at the 2- to 4-leaf stage; in some cases (as stated), application of individual active compounds or active compound combinations was carried out pre-emergence (cf. Example 1) or as a sequential treatment partly pre-emergence and/or post-emergence.

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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)
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  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
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US09/353,230 1998-07-16 1999-07-14 Herbicidal compositions Abandoned US20020123428A1 (en)

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US13/722,689 US8791050B2 (en) 1998-07-16 2012-12-20 Herbicidal compositions
US13/722,630 US8765638B2 (en) 1998-07-16 2012-12-20 Herbicidal compositions

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DE19832017.5 1998-07-16
DE19832017A DE19832017A1 (de) 1998-07-16 1998-07-16 Herbizide Mittel mit substituierten Phenylsulfonylharnstoffen zur Unkrautbekämpfung in Reis
DE19928387.7 1999-06-22
DE1999128387 DE19928387A1 (de) 1999-06-22 1999-06-22 Herbizide Mittel

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US13/722,630 Expired - Lifetime US8765638B2 (en) 1998-07-16 2012-12-20 Herbicidal compositions
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US20030069138A1 (en) 2003-04-10
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US8791050B2 (en) 2014-07-29
MX240920B (enrdf_load_stackoverflow) 2006-10-09
DE59912021D1 (de) 2005-06-09
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US8765638B2 (en) 2014-07-01
EP1104232B8 (de) 2010-10-27
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AR019919A1 (es) 2002-03-27
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AU4782099A (en) 2000-02-07
US20130130899A1 (en) 2013-05-23
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KR100913892B1 (ko) 2009-08-26
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