US20050009705A1 - Selective herbicides based on substituted thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)ones and safeners - Google Patents

Selective herbicides based on substituted thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)ones and safeners Download PDF

Info

Publication number
US20050009705A1
US20050009705A1 US10/489,092 US48909204A US2005009705A1 US 20050009705 A1 US20050009705 A1 US 20050009705A1 US 48909204 A US48909204 A US 48909204A US 2005009705 A1 US2005009705 A1 US 2005009705A1
Authority
US
United States
Prior art keywords
substituted
chlorine
ethyl
cyano
methyl
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.)
Abandoned
Application number
US10/489,092
Other languages
English (en)
Inventor
Dieter Feucht
Peter Dahmen
Mark Drewes
Rolf Pontzen
Ernst Gesing
Hans-Georg Schwarz
Klaus-Helmut Muller
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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 Bayer CropScience AG filed Critical Bayer CropScience AG
Assigned to BAYER CROPSCIENCE AG reassignment BAYER CROPSCIENCE AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DREWES, MARK WILHELM, FEUCHT, DIETER, DAHMEN, PETER, PONTZEN, ROLF, SCHWARTZ, HANS-GEORG, GESING, ERNST RUDOLF F., MULLER, KLAUS-HELMUT
Publication of US20050009705A1 publication Critical patent/US20050009705A1/en
Priority to US13/873,656 priority Critical patent/US9968091B2/en
Assigned to BAYER INTELLECTUAL PROPERTY GMBH reassignment BAYER INTELLECTUAL PROPERTY GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAYER CROPSCIENCE AG
Assigned to BAYER INTELLECTUAL PROPERTY GMBH reassignment BAYER INTELLECTUAL PROPERTY GMBH CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 034892 FRAME: 0286. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Assignors: BAYER CROPSCIENCE AG
Priority to US14/950,588 priority patent/US10524475B2/en
Assigned to BAYER CROPSCIENCE AKTIENGESELLSCHAFT reassignment BAYER CROPSCIENCE AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAYER INTELLECTUAL PROPERTY GMBH
Priority to US16/690,200 priority patent/US20200085058A1/en
Abandoned 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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

Definitions

  • the invention relates to novel selective herbicidal active compound combinations which comprise substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones and at least one compound which improves crop plant compatibility and which can be used with particularly good results for the selective control of weeds in various crops of useful plants.
  • the invention provides selective herbicidal compositions, characterized by an effective amount of an active compound combination comprising
  • hydrocarbon chains such as in alkyl or alkanediyl
  • the hydrocarbon chains are in each case straight-chain or branched—including in combination with hetero atoms, such as in alkoxy.
  • R 1 and R 2 represent methyl, ethyl, n- or i-propyl.
  • Preferred active compound components of group 1 are in particular also the sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 -alkylammonium-, di-(C 1 -C 4 -alkyl)ammonium-, tri-(C 1 -C 4 -alkyl)ammonium, tetra-(C 1 -C 4 -alkyl)ammonium, tri-(C 1 -C 4 -alkyl)sulphonium-, C 5 - or C 6 -cycloalkylammonium and di-(C 1 -C 2 -alkyl)-benzylammonium salts of compounds of the formula (I) in which Q 1 , Q 2 , R 1 , R 2 , R 3 and R 4 have the meanings given above as being preferred.
  • herbicide safeners of the formulae (Ia), (IIb), (IIc), (IId) and (IIe) are defined below.
  • Table 2 Examples of the compounds of the formula (IIa) (IIa) Example No. (positions) (X 1 ) n A 1 R 5 IIa-1 (2) Cl, (4) Cl OCH 3 IIa-2 (2) Cl, (4) Cl OCH 3 IIa-3 (2) Cl, (4) Cl OC 2 H 5 IIa-4 (2) Cl, (4) Cl OC 2 H 5 IIa-5 (2) Cl OCH 3 IIa-6 (2) Cl, (4) Cl OCH 3 IIa-7 (2) F OCH 3 IIa-8 (2) F OCH 3 IIa-9 (2) Cl, (4) Cl OC 2 H 5 IIa-10 (2) Cl, (4) CF 3 OCH 3 IIa-11 (2) Cl OCH 3 IIa-12 — OC 2 H 5 IIa-13 (2) Cl, (4) Cl OC 2 H 5 IIa-14 (2) Cl, (4) Cl OC 2 H 5 IIa-15 (2) Cl, (4) Cl OC 2 H 5 IIa-16 (2) Cl, (4) Cl OC 2 H 5 IIa-17 (2) Cl, (4) Cl OC 2 H 5 H 5
  • the compounds of the general formula (IIa) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-91/07874, WO-A-95/07897).
  • the compounds of the general formula (IIb) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. EP-A-191736).
  • the compounds of the general formula (IIc) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-22180974, DE-A-2350547).
  • the compounds of the general formula (IId) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-19621522/U.S. Pat. No. 6,235,680/WO 97/45016).
  • the compounds of the general formula (IIe) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-99/66795/U.S. Pat. No. 6,251,827).
  • the active compound combinations according to the invention can be used, for example, in connection with the following plants:
  • crop plants are all plants and plant varieties including transgenic plants and plant varieties, where on transgenic plants and plant varieties it is also possible for synergistic effects to occur.
  • the advantageous effect of the crop plant compatibility of the active compound combinations according to the invention is particularly highly pronounced at certain concentration ratios.
  • the weight ratios of the active compounds in the active compound concentrations can be varied within relatively wide ranges. In general, 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, and particularly preferably 0.1 to 50 parts by weight and most preferably 1 to 25 parts by weight of one of the compounds which improve crop plant compatibility mentioned under group 2 above (antidotes/safeners) are present per part by weight of active compound of the formula (I) or its salts.
  • the active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
  • formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
  • Suitable liquid solvents are essentially: aromatics, such as xylene. toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.
  • aromatics such as xylene. toluene or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chlor
  • Suitable solid carriers are:
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
  • Other possible additives are mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally comprise from 0.1 to 95 per cent by weight of active compounds including the safeners, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active compounds contained in the active compound combinations can also be mixed in individual formulations when used, i.e. in the form of tank mixes.
  • novel active compound combinations can furthermore be used as a mixture with other known herbicides, finished formulations or tank mixes again being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, growth factors, plant nutrients and agents which improve soil structure, is also possible.
  • novel active compound combinations can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by washing, spraying, atomizing, dusting or scattering.
  • the amounts of the active compound combinations according to the invention applied can be varied within a certain range; they depend, inter alia. on the weather and on soil factors. In general, the application rates are between 0.001 and 5 kg per ha, preferably between 0.001 and 1 kg per ha, particularly preferably between 0.003 and 0.5 kg per ha.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say by the pre-emergence and post-emergence method.
  • the active compound or safener components are in each case dissolved in a few ml (generally 2-3 ml) of solvent (generally acetone or N,N-dimethyl-formamide), and the solutions are combined and then—if appropriate after addition of an emulsifier—diluted with water to the desired concentration.
  • solvent generally acetone or N,N-dimethyl-formamide
  • an aqueous spray liquor was prepared using 0.1% of the additive Renex-36.
  • test plants are grown under controlled conditions (temperature, light, atmospheric humidity) in a greenhouse.
  • the test plants are sprayed when they have reached a height of 5-15 cm.
  • concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 500 l of water/ha.
  • the pots with the test plants are kept in a greenhouse chamber under controlled conditions (temperature, light, atmospheric humidity) until the test has ended. About three weeks after the application, the degree of damage to the crop plants is rated in % damage in comparison to the development of the untreated control.
  • an aqueous spray liquor comprising 0.5% of the additive Renex-36 was prepared.
  • Ex.-No. IId-25 TABLE A-2-1 Post-emergence test/greenhouse Damage winter Active compound Application rate barley (+ safener) (g of a.i./ha) (in %) I-2, sodium salt 4 60 2 50 I-2, sodium salt + 4 + 100 50 Comp. No. IId-25 2 + 100 25 4 + 30 50 2 + 30 35
  • the compound I-2 was used as 10 WP.
  • Marlipal® was added in an amount of 500 ml/ha.
  • Maize 3 maize of the cultivar “LIXIS” TABLE A-3-1 Post-emergence test/greenhouse Damage Application rate maize 1 Active compound (+ safener) (g of a.i./ha) (in %) I-2 15 20 8 10 I-2 + Comp. No. IId-25 15 + 100 5 8 + 100 0
  • Mefenpyr-diethyl was used as 100 EC.
  • Mefenpyr-diethyl was used as 100 EC and the compound of Ex. No. I-2 was used as 10 WP. TABLE A-5-1 Post-emergence test/greenhouse Application rate Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in %) I-2 30 60 mefenpyr-diethyl 50 0 I-2 + mefenpyr-diethyl 30 + 50 5

Landscapes

  • 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)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US10/489,092 2001-09-21 2002-09-10 Selective herbicides based on substituted thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)ones and safeners Abandoned US20050009705A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US13/873,656 US9968091B2 (en) 2001-09-21 2013-04-30 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners
US14/950,588 US10524475B2 (en) 2001-09-21 2015-11-24 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners
US16/690,200 US20200085058A1 (en) 2001-09-21 2019-11-21 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10146590.4 2001-09-21
DE10146590A DE10146590A1 (de) 2001-09-21 2001-09-21 Selektive Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und Safenern
PCT/EP2002/010104 WO2003026427A1 (de) 2001-09-21 2002-09-10 Selektive herbizide auf basis von substituierten thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und safenern

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/010104 A-371-Of-International WO2003026427A1 (de) 2001-09-21 2002-09-10 Selektive herbizide auf basis von substituierten thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und safenern

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/873,656 Continuation US9968091B2 (en) 2001-09-21 2013-04-30 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners

Publications (1)

Publication Number Publication Date
US20050009705A1 true US20050009705A1 (en) 2005-01-13

Family

ID=7699812

Family Applications (4)

Application Number Title Priority Date Filing Date
US10/489,092 Abandoned US20050009705A1 (en) 2001-09-21 2002-09-10 Selective herbicides based on substituted thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)ones and safeners
US13/873,656 Expired - Lifetime US9968091B2 (en) 2001-09-21 2013-04-30 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners
US14/950,588 Expired - Lifetime US10524475B2 (en) 2001-09-21 2015-11-24 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners
US16/690,200 Abandoned US20200085058A1 (en) 2001-09-21 2019-11-21 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners

Family Applications After (3)

Application Number Title Priority Date Filing Date
US13/873,656 Expired - Lifetime US9968091B2 (en) 2001-09-21 2013-04-30 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners
US14/950,588 Expired - Lifetime US10524475B2 (en) 2001-09-21 2015-11-24 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners
US16/690,200 Abandoned US20200085058A1 (en) 2001-09-21 2019-11-21 Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners

Country Status (24)

Country Link
US (4) US20050009705A1 (el)
EP (1) EP1429613B1 (el)
JP (2) JP4610895B2 (el)
KR (2) KR100927025B1 (el)
CN (1) CN1326457C (el)
AR (1) AR036775A1 (el)
AU (1) AU2002333811B8 (el)
BE (2) BE2016C043I2 (el)
CA (2) CA2460922C (el)
CO (1) CO5580725A2 (el)
DE (2) DE10146590A1 (el)
ES (1) ES2280615T3 (el)
FR (2) FR17C1034I2 (el)
HR (1) HRP20040359A2 (el)
HU (3) HU230218B1 (el)
MX (1) MXPA04002641A (el)
NL (3) NL350074I2 (el)
PL (1) PL207754B1 (el)
PT (1) PT1429613E (el)
RS (1) RS51046B (el)
RU (1) RU2308834C2 (el)
UA (1) UA77010C2 (el)
WO (1) WO2003026427A1 (el)
ZA (1) ZA200402129B (el)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050014809A1 (en) * 2001-11-02 2005-01-20 Ernst-Rudolf Gesing Substituted thien-3-yl-sulphonylamino(thio)carbonyl-triazolin(thi)ones
US20070054807A1 (en) * 2005-09-08 2007-03-08 Bayer Cropscience Gmbh Storage-stable formulations of sulfonamides
US20140094363A1 (en) * 2004-07-20 2014-04-03 Bayer Intellectual Property Gmbh Active Substance for Increasing Pathogenic Defense in Plants and Methods for the Defection Thereof
US10820591B2 (en) * 2016-11-07 2020-11-03 Bayer Aktiengesellschaft Substituted sulfonyl amides for controlling animal pests

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10146590A1 (de) * 2001-09-21 2003-04-10 Bayer Cropscience Ag Selektive Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und Safenern
DE10146591A1 (de) * 2001-09-21 2003-04-10 Bayer Cropscience Ag Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen
DE102004025220A1 (de) * 2004-05-22 2005-12-08 Bayer Cropscience Gmbh Ölsuspensionskonzentrat
DE102004010812A1 (de) * 2004-03-05 2005-09-22 Bayer Cropscience Ag Unkrautbekämpfungsverfahren
DE102004010813A1 (de) 2004-03-05 2005-11-10 Bayer Cropscience Ag Neue Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)onen und 4-HPPD-Hemmstoffen
WO2007057107A1 (de) 2005-11-17 2007-05-24 Bayer Cropscience Ag Wässriges herbizides mittel auf basis eines suspensionskonzentrats enthaltend herbizide und safener
EP2071950A1 (de) 2007-12-20 2009-06-24 Bayer CropScience AG Verfahren zur Authentizitätsprüfung von Pflanzenschutzmitteln mittels Isotopen
CN103980098B (zh) * 2014-05-16 2016-07-13 上海康鹏化学有限公司 含二氟甲氧醚桥键（cf2o）的单体液晶化合物的制备方法
BR102020019868A2 (pt) * 2020-09-28 2022-04-12 Upl Do Brasil Industria E Comercio De Insumos Agropecuarios S.A. Combinações de herbicidas triazolonas com fitoprotetores
WO2023083897A1 (en) 2021-11-11 2023-05-19 Bayer Aktiengesellschaft Surfactant combination for aqueous agrochemical (crop protection) suspension formulations with high salt content and low-concentration of sulfonylurea herbicide

Citations (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4021224A (en) * 1971-12-09 1977-05-03 Stauffer Chemical Company Herbicide compositions
US4137070A (en) * 1971-04-16 1979-01-30 Stauffer Chemical Company Herbicide compositions
US4186130A (en) * 1973-05-02 1980-01-29 Stauffer Chemical Company N-(haloalkanoyl) oxazolidines
US4243811A (en) * 1972-10-13 1981-01-06 Stauffer Chemical Company 2,2,4-Trimethyl-4-hydroxymethyl-3-dichloroacetyl oxazolidine
US4269618A (en) * 1971-12-09 1981-05-26 Stauffer Chemical Company Herbicide compositions
US4415353A (en) * 1971-04-16 1983-11-15 Stauffer Chemical Company Herbicide compositions
US4415352A (en) * 1971-04-16 1983-11-15 Stauffer Chemical Company Herbicide compositions
US4623727A (en) * 1982-02-17 1986-11-18 Ciba-Geigy Corporation 8-hydroxy-quinoline derivatives for the protection of cultivated plants
US4639266A (en) * 1984-09-11 1987-01-27 Hoechst Aktiengesellschaft Plant protection agents based on 1,2,4-triazole derivatives and also new derivatives of 1,2,4-triazole
US4708735A (en) * 1971-04-16 1987-11-24 Stauffer Chemical Co. Herbicide compositions
US4881966A (en) * 1985-02-14 1989-11-21 Ciba-Geigy Corporation Use of quinoline derivatives for the protection of cultivated plants
US4891057A (en) * 1986-10-04 1990-01-02 Hoechst Aktiengesellschaft Phenylpyrazolecarboxylic acid derivatives, their preparation, and their use as plant-growth regulators and safeners
US4902340A (en) * 1982-05-07 1990-02-20 Ciba-Geigy Corporation Use of quinoline derivatives for the protection of cultivated plants from herbicides
US4964893A (en) * 1986-04-17 1990-10-23 Monsanto Company Benzhydryl compounds as herbicide antidotes
US4971618A (en) * 1971-04-16 1990-11-20 Ici Americas Inc. Herbicide compositions
US5061311A (en) * 1987-03-24 1991-10-29 Bayer Aktiengesellschaft Substituted triazolinone herbicides and plant growth regulators
US5149356A (en) * 1988-05-09 1992-09-22 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5166356A (en) * 1987-03-24 1992-11-24 Bayer Aktiengesellschaft Substituted triazolinone herbicides and plant growth regulators
US5262389A (en) * 1987-03-24 1993-11-16 Bayer Aktiengesellschaft Substituted triazolinone herbicides and plant growth regulators
US5276162A (en) * 1988-05-09 1994-01-04 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5314863A (en) * 1989-11-25 1994-05-24 Hoechst Aktiengesellschaft Isoxazolines, their preparation, and their use as plant-protecting agents
US5380852A (en) * 1990-12-21 1995-01-10 Hoechst Aktiengesellschaft 5-chloroquinolin-8-oxyalkanecarboxylic acid derivatives, useful as antidotes for herbicides
US5380863A (en) * 1989-10-12 1995-01-10 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5401700A (en) * 1988-03-17 1995-03-28 Hoechst Aktiengesellschaft Plant protection agents based on pyrazolecarboxylic acid derivatives
US5407897A (en) * 1993-03-03 1995-04-18 American Cyanamid Company Method for safening herbicides in crops using substituted benzopyran and tetrahydronaphthalene compounds
US5516750A (en) * 1993-09-16 1996-05-14 Hoechst Schering Agrevo Gmbh Substituted isoxazolines, process for their preparation, composition containing them, and their use of safeners
US5552369A (en) * 1992-10-15 1996-09-03 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
US5599944A (en) * 1987-03-24 1997-02-04 Bayer Aktiengesellschaft Intermediates for herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5700758A (en) * 1989-11-30 1997-12-23 Hoechst Aktiengesellschaft Pyrazolines for protecting crop plants against herbicides
US5703008A (en) * 1989-11-30 1997-12-30 Hoechst Aktiengesellschaft Pyrazolines for protecting crop plants against herbicides
US5739076A (en) * 1992-07-24 1998-04-14 Exxon Chemical Patents Inc. Catalysts and their use in oxidation of saturated hydrocarbons
US6121204A (en) * 1995-03-08 2000-09-19 Bayer Aktiengesellschaft Herbicidal or fungicidal sulphonylaminocarbonyltriazolinones with halogenated alk(en)oxy substituents
US6162762A (en) * 1998-01-12 2000-12-19 Novartis Crop Protection, Inc. Herbicidal composition
US6235680B1 (en) * 1996-05-29 2001-05-22 Hoechst Schering Agrevo Gmbh N-acylsulfonamides, novel mixtures of herbicides and antidotes, and their use
US6251827B1 (en) * 1997-09-29 2001-06-26 Hoechst Schering Agrevo Gmbh Acylsulfamoylbenzamides, crop protection compositions comprising them, and processes for their preparation
US6482947B1 (en) * 1992-08-01 2002-11-19 Hoechst Aktiengesellschaft Substituted (hetero) aryl compounds, process for their preparation, agents containing them and their use as safeners
US6511940B1 (en) * 1998-06-23 2003-01-28 Hoechst Schering Agrevo Gmbh Combination of herbicides and safeners
US6964939B1 (en) * 1999-07-15 2005-11-15 Bayer Aktiengesellschaft Substituted thiene-3-yl-sulfonyl amino(thio)carbonyl-triazolin(thi)ones

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3817192A1 (de) 1988-05-20 1989-11-30 Hoechst Ag 1,2,4-triazolderivate enthaltende pflanzenschuetzende mittel sowie neue derivate des 1,2,4-triazols
DE19940860A1 (de) * 1999-08-27 2001-03-01 Bayer Ag Selektive Herbizide auf Basis eines substituierten Phenylsulfonyl aminocarbonyltriazolinons und Safenern II
DE10031825A1 (de) * 2000-06-30 2002-01-10 Bayer Ag Selektive Herbizide auf Basis von Arylsulfonylaminocarbonyltriazolinonen
DE10146591A1 (de) * 2001-09-21 2003-04-10 Bayer Cropscience Ag Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen
DE10146590A1 (de) * 2001-09-21 2003-04-10 Bayer Cropscience Ag Selektive Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und Safenern

Patent Citations (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4708735A (en) * 1971-04-16 1987-11-24 Stauffer Chemical Co. Herbicide compositions
US4137070A (en) * 1971-04-16 1979-01-30 Stauffer Chemical Company Herbicide compositions
US4415353A (en) * 1971-04-16 1983-11-15 Stauffer Chemical Company Herbicide compositions
US4415352A (en) * 1971-04-16 1983-11-15 Stauffer Chemical Company Herbicide compositions
US4971618A (en) * 1971-04-16 1990-11-20 Ici Americas Inc. Herbicide compositions
US4269618A (en) * 1971-12-09 1981-05-26 Stauffer Chemical Company Herbicide compositions
US4021224A (en) * 1971-12-09 1977-05-03 Stauffer Chemical Company Herbicide compositions
US4243811A (en) * 1972-10-13 1981-01-06 Stauffer Chemical Company 2,2,4-Trimethyl-4-hydroxymethyl-3-dichloroacetyl oxazolidine
US4186130A (en) * 1973-05-02 1980-01-29 Stauffer Chemical Company N-(haloalkanoyl) oxazolidines
US4785106A (en) * 1982-02-17 1988-11-15 Ciba-Geigy Corporation 8-hydroxy ether quinoline derivatives
US4758264A (en) * 1982-02-17 1988-07-19 Ciba-Geigy Corporation Use of quinoline derivatives for the protection of cultivated plants
US4785105A (en) * 1982-02-17 1988-11-15 Ciba-Geigy Corporation 8-hydroxy ether quinoline derivatives
US4822884A (en) * 1982-02-17 1989-04-18 Ciba-Geigy Corporation Quinoline derivatives for the protection of cultivated plants
US4851033A (en) * 1982-02-17 1989-07-25 Ciba-Geigy Corporation Use of quinoline derivatives for the protection of cultivated plants
US4623727A (en) * 1982-02-17 1986-11-18 Ciba-Geigy Corporation 8-hydroxy-quinoline derivatives for the protection of cultivated plants
US5045107A (en) * 1982-02-17 1991-09-03 Ciba-Geigy Corporation Use of quinoline derivatives for the protection of cultivated plants
US5102445A (en) * 1982-05-07 1992-04-07 Ciba-Geigy Corporation Use of quinoline derivatives for the protection of cultivated plants
US4902340A (en) * 1982-05-07 1990-02-20 Ciba-Geigy Corporation Use of quinoline derivatives for the protection of cultivated plants from herbicides
US5023333A (en) * 1982-05-07 1991-06-11 Ciba-Geigy Corporation Derivatives of 8-hydroxyquinoline
US4639266A (en) * 1984-09-11 1987-01-27 Hoechst Aktiengesellschaft Plant protection agents based on 1,2,4-triazole derivatives and also new derivatives of 1,2,4-triazole
US4881966A (en) * 1985-02-14 1989-11-21 Ciba-Geigy Corporation Use of quinoline derivatives for the protection of cultivated plants
US4964893A (en) * 1986-04-17 1990-10-23 Monsanto Company Benzhydryl compounds as herbicide antidotes
US4891057A (en) * 1986-10-04 1990-01-02 Hoechst Aktiengesellschaft Phenylpyrazolecarboxylic acid derivatives, their preparation, and their use as plant-growth regulators and safeners
US5082949A (en) * 1986-10-04 1992-01-21 Hoechst Aktiengesellschaft Phenylpyrazolecarboxylic acid derivative preparation
US5262389A (en) * 1987-03-24 1993-11-16 Bayer Aktiengesellschaft Substituted triazolinone herbicides and plant growth regulators
US5166356A (en) * 1987-03-24 1992-11-24 Bayer Aktiengesellschaft Substituted triazolinone herbicides and plant growth regulators
US5061311A (en) * 1987-03-24 1991-10-29 Bayer Aktiengesellschaft Substituted triazolinone herbicides and plant growth regulators
US5599944A (en) * 1987-03-24 1997-02-04 Bayer Aktiengesellschaft Intermediates for herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5523409A (en) * 1987-03-24 1996-06-04 Bayer Aktiengesellschaft Substituted triazolinone herbicides and plant growth regulators
US5750718A (en) * 1987-03-24 1998-05-12 Bayer Aktiengesellschaft Intermediates for herbicidal sulphonyl-aminocarbonlyltriazolinones having substituents which are bonded via sulphur
US5401700A (en) * 1988-03-17 1995-03-28 Hoechst Aktiengesellschaft Plant protection agents based on pyrazolecarboxylic acid derivatives
US5945541A (en) * 1988-03-17 1999-08-31 Hoechst Schering Agrevo Gmbh Plant protection agents based on pyrazolecarboxylic acid derivatives
US5276162A (en) * 1988-05-09 1994-01-04 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5149356A (en) * 1988-05-09 1992-09-22 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5380863A (en) * 1989-10-12 1995-01-10 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5314863A (en) * 1989-11-25 1994-05-24 Hoechst Aktiengesellschaft Isoxazolines, their preparation, and their use as plant-protecting agents
US5703008A (en) * 1989-11-30 1997-12-30 Hoechst Aktiengesellschaft Pyrazolines for protecting crop plants against herbicides
US5700758A (en) * 1989-11-30 1997-12-23 Hoechst Aktiengesellschaft Pyrazolines for protecting crop plants against herbicides
US5380852A (en) * 1990-12-21 1995-01-10 Hoechst Aktiengesellschaft 5-chloroquinolin-8-oxyalkanecarboxylic acid derivatives, useful as antidotes for herbicides
US5739076A (en) * 1992-07-24 1998-04-14 Exxon Chemical Patents Inc. Catalysts and their use in oxidation of saturated hydrocarbons
US6482947B1 (en) * 1992-08-01 2002-11-19 Hoechst Aktiengesellschaft Substituted (hetero) aryl compounds, process for their preparation, agents containing them and their use as safeners
US5654438A (en) * 1992-10-15 1997-08-05 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
US5552369A (en) * 1992-10-15 1996-09-03 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
US5696050A (en) * 1993-03-03 1997-12-09 American Cyanamid Company Method for safening herbicides in crops using substituted benzopyran and tetrahydronaphthalene compounds
US5516918A (en) * 1993-03-03 1996-05-14 American Cyanamid Company Substituted benzopyran and tetrahydronaphthalene compounds useful for safening herbicides in crops
US5407897A (en) * 1993-03-03 1995-04-18 American Cyanamid Company Method for safening herbicides in crops using substituted benzopyran and tetrahydronaphthalene compounds
US5516750A (en) * 1993-09-16 1996-05-14 Hoechst Schering Agrevo Gmbh Substituted isoxazolines, process for their preparation, composition containing them, and their use of safeners
US6121204A (en) * 1995-03-08 2000-09-19 Bayer Aktiengesellschaft Herbicidal or fungicidal sulphonylaminocarbonyltriazolinones with halogenated alk(en)oxy substituents
US6235680B1 (en) * 1996-05-29 2001-05-22 Hoechst Schering Agrevo Gmbh N-acylsulfonamides, novel mixtures of herbicides and antidotes, and their use
US6251827B1 (en) * 1997-09-29 2001-06-26 Hoechst Schering Agrevo Gmbh Acylsulfamoylbenzamides, crop protection compositions comprising them, and processes for their preparation
US6162762A (en) * 1998-01-12 2000-12-19 Novartis Crop Protection, Inc. Herbicidal composition
US6511940B1 (en) * 1998-06-23 2003-01-28 Hoechst Schering Agrevo Gmbh Combination of herbicides and safeners
US20030171220A1 (en) * 1998-06-23 2003-09-11 Frank Ziemer Combinations of herbicides and safeners
US6964939B1 (en) * 1999-07-15 2005-11-15 Bayer Aktiengesellschaft Substituted thiene-3-yl-sulfonyl amino(thio)carbonyl-triazolin(thi)ones

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050014809A1 (en) * 2001-11-02 2005-01-20 Ernst-Rudolf Gesing Substituted thien-3-yl-sulphonylamino(thio)carbonyl-triazolin(thi)ones
US7410933B2 (en) * 2001-11-02 2008-08-12 Bayer Cropscience Ag Substituted thiene-3-ylsulphonylamino(thio)carbonyl-triazolin(thi)ones
US20140094363A1 (en) * 2004-07-20 2014-04-03 Bayer Intellectual Property Gmbh Active Substance for Increasing Pathogenic Defense in Plants and Methods for the Defection Thereof
US20070054807A1 (en) * 2005-09-08 2007-03-08 Bayer Cropscience Gmbh Storage-stable formulations of sulfonamides
US8158557B2 (en) 2005-09-08 2012-04-17 Bayer Cropscience Ag Storage-stable formulations of sulfonamides
US10820591B2 (en) * 2016-11-07 2020-11-03 Bayer Aktiengesellschaft Substituted sulfonyl amides for controlling animal pests

Also Published As

Publication number Publication date
EP1429613B1 (de) 2007-01-17
CA2695675A1 (en) 2003-04-03
US20160073635A1 (en) 2016-03-17
NL350074I2 (el) 2016-09-01
EP1429613A1 (de) 2004-06-23
UA77010C2 (uk) 2006-10-16
HUP0402116A3 (en) 2005-10-28
JP2005503421A (ja) 2005-02-03
CA2695675C (en) 2013-04-23
AU2002333811B8 (en) 2008-09-11
HUS000505I2 (hu) 2021-03-29
US9968091B2 (en) 2018-05-15
RU2004112214A (ru) 2005-10-10
PL367511A1 (en) 2005-02-21
BE2017C050I2 (el) 2021-11-22
CA2460922C (en) 2011-07-05
HUS2000029I1 (hu) 2021-03-29
HU230218B1 (hu) 2015-10-28
CO5580725A2 (es) 2005-11-30
KR20090105978A (ko) 2009-10-07
KR100979997B1 (ko) 2010-09-03
PL207754B1 (pl) 2011-01-31
FR18C1015I2 (fr) 2019-06-21
CN1555221A (zh) 2004-12-15
PT1429613E (pt) 2007-03-30
HUS1600007I1 (hu) 2018-11-28
NL350078I1 (nl) 2017-02-08
WO2003026427A1 (de) 2003-04-03
US20200085058A1 (en) 2020-03-19
FR18C1015I1 (el) 2018-06-15
US10524475B2 (en) 2020-01-07
MXPA04002641A (es) 2004-06-07
HUP0402116A2 (hu) 2005-01-28
JP2010100638A (ja) 2010-05-06
RS51046B (sr) 2010-10-31
FR17C1034I2 (fr) 2019-08-09
RS24504A (en) 2006-12-15
ZA200402129B (en) 2005-06-29
KR100927025B1 (ko) 2009-11-19
CA2460922A1 (en) 2003-04-03
NL350082I2 (nl) 2018-01-24
BE2016C043I2 (el) 2021-07-19
AR036775A1 (es) 2004-10-06
HRP20040359B1 (el) 2012-11-30
US20130237418A1 (en) 2013-09-12
ES2280615T3 (es) 2007-09-16
RU2308834C2 (ru) 2007-10-27
FR17C1034I1 (el) 2017-10-27
KR20040053119A (ko) 2004-06-23
HRP20040359A2 (en) 2005-04-30
DE50209305D1 (de) 2007-03-08
CN1326457C (zh) 2007-07-18
NL350078I2 (nl) 2017-07-11
JP4610895B2 (ja) 2011-01-12
AU2002333811B2 (en) 2008-08-14
DE10146590A1 (de) 2003-04-10

Similar Documents

Publication Publication Date Title
US10524475B2 (en) Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners
US7432225B2 (en) Selective herbicides based on substituted cyclic keto-enols and safeners
ZA200603505B (en) 2-halogen-6-alkyl-phenyl-substituted tetramic acid derivatives
JP2005503421A5 (ja) 置換チエン−３−イル−スルホニルアミノ（チオ）−カルボニルトリアゾリン（チ）オンおよび毒性緩和剤をベースとする選択的除草剤
US20060160703A1 (en) Selective herbicides based on substituted cyclic dicarbonyl compounds and safeners
US20040132619A1 (en) Selective substituted aryl ketone and safener based herbicides

Legal Events

Date Code Title Description
AS Assignment

Owner name: BAYER CROPSCIENCE AG, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:FEUCHT, DIETER;DAHMEN, PETER;DREWES, MARK WILHELM;AND OTHERS;REEL/FRAME:015826/0044;SIGNING DATES FROM 20040218 TO 20040601

STCB Information on status: application discontinuation

Free format text: ABANDONED -- AFTER EXAMINER'S ANSWER OR BOARD OF APPEALS DECISION

AS Assignment

Owner name: BAYER INTELLECTUAL PROPERTY GMBH, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BAYER CROPSCIENCE AG;REEL/FRAME:034892/0286

Effective date: 20141217

AS Assignment

Owner name: BAYER INTELLECTUAL PROPERTY GMBH, GERMANY

Free format text: CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 034892 FRAME: 0286. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT;ASSIGNOR:BAYER CROPSCIENCE AG;REEL/FRAME:035071/0680

Effective date: 20141217

AS Assignment

Owner name: BAYER CROPSCIENCE AKTIENGESELLSCHAFT, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BAYER INTELLECTUAL PROPERTY GMBH;REEL/FRAME:047403/0243

Effective date: 20180608