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 PDFInfo
- 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
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- 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
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- 0 [1*]OC(=O)C1=CSC([2*])=C1S(=O)(=O)NC(=C)N1N=C([3*])N([4*])C1=C Chemical compound [1*]OC(=O)C1=CSC([2*])=C1S(=O)(=O)NC(=C)N1N=C([3*])N([4*])C1=C 0.000 description 27
- VNXBKJFUJUWOCW-UHFFFAOYSA-N CC1CC1 Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 13
- DTXMGLLAMAWYNE-UHFFFAOYSA-N CC1=NN(C)C(C2=CC=CC=C2)=C1 Chemical compound CC1=NN(C)C(C2=CC=CC=C2)=C1 DTXMGLLAMAWYNE-UHFFFAOYSA-N 0.000 description 3
- KDKYADYSIPSCCQ-UHFFFAOYSA-N C#CCC Chemical compound C#CCC KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- FMMNYHZCBVJMDE-UHFFFAOYSA-N CC1=NN(C)C(C2=CC=CC=C2F)=C1 Chemical compound CC1=NN(C)C(C2=CC=CC=C2F)=C1 FMMNYHZCBVJMDE-UHFFFAOYSA-N 0.000 description 2
- WLGWHHKJFPUADB-UHFFFAOYSA-N CCC1CC(C)=NO1 Chemical compound CCC1CC(C)=NO1 WLGWHHKJFPUADB-UHFFFAOYSA-N 0.000 description 2
- VNKYTQGIUYNRMY-UHFFFAOYSA-N CCCOC Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 2
- NVJUHMXYKCUMQA-UHFFFAOYSA-N CCCOCC Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 2
- LSZLGSOAXUQCFF-UHFFFAOYSA-N CCOC(=O)C1(C)CC(C)=NN1C Chemical compound CCOC(=O)C1(C)CC(C)=NN1C LSZLGSOAXUQCFF-UHFFFAOYSA-N 0.000 description 2
- XGJFAHSPFFOJNW-UHFFFAOYSA-N COC(=O)C1(C)CC(C)=NN1C Chemical compound COC(=O)C1(C)CC(C)=NN1C XGJFAHSPFFOJNW-UHFFFAOYSA-N 0.000 description 2
- QNBDJTKBKITRJI-UHFFFAOYSA-N C=CCOC(=O)C(C)C Chemical compound C=CCOC(=O)C(C)C QNBDJTKBKITRJI-UHFFFAOYSA-N 0.000 description 1
- YOBITCIOUKNPDI-UHFFFAOYSA-N C=CCOCC(C)OC Chemical compound C=CCOCC(C)OC YOBITCIOUKNPDI-UHFFFAOYSA-N 0.000 description 1
- HNOQAFMOBRWDKQ-UHFFFAOYSA-N CC1=CC(C)=NN1C Chemical compound CC1=CC(C)=NN1C HNOQAFMOBRWDKQ-UHFFFAOYSA-N 0.000 description 1
- YHLDCNVXXHTZAE-UHFFFAOYSA-N CC1=NN(C)C(C(C)(C)C)=C1 Chemical compound CC1=NN(C)C(C(C)(C)C)=C1 YHLDCNVXXHTZAE-UHFFFAOYSA-N 0.000 description 1
- VGIPFSZAJPAOPJ-UHFFFAOYSA-N CC1=NN(C)C(C(C)C)=C1 Chemical compound CC1=NN(C)C(C(C)C)=C1 VGIPFSZAJPAOPJ-UHFFFAOYSA-N 0.000 description 1
- XRYAKWGFASOQAV-UHFFFAOYSA-N CC1=NN(C)C(C(Cl)(Cl)Cl)=N1 Chemical compound CC1=NN(C)C(C(Cl)(Cl)Cl)=N1 XRYAKWGFASOQAV-UHFFFAOYSA-N 0.000 description 1
- RLBLAYDWERJPDV-UHFFFAOYSA-N CC1=NN(C)C(C2=CC=CC=C2)=N1 Chemical compound CC1=NN(C)C(C2=CC=CC=C2)=N1 RLBLAYDWERJPDV-UHFFFAOYSA-N 0.000 description 1
- CRWRYJWUDBEZSK-UHFFFAOYSA-N CC1=NN(C)C(C2=CC=CC=C2Cl)=C1 Chemical compound CC1=NN(C)C(C2=CC=CC=C2Cl)=C1 CRWRYJWUDBEZSK-UHFFFAOYSA-N 0.000 description 1
- VFDYFGREKXNZCA-UHFFFAOYSA-N CC1=NOC(C)(C2=CC=CC=C2)C1 Chemical compound CC1=NOC(C)(C2=CC=CC=C2)C1 VFDYFGREKXNZCA-UHFFFAOYSA-N 0.000 description 1
- JXOVTPNBOKLRHT-UHFFFAOYSA-N CC1=NOC(C)C1 Chemical compound CC1=NOC(C)C1 JXOVTPNBOKLRHT-UHFFFAOYSA-N 0.000 description 1
- FXPMNNZCCKEAMG-UHFFFAOYSA-N CC1CN(C)C(C)(C)O1 Chemical compound CC1CN(C)C(C)(C)O1 FXPMNNZCCKEAMG-UHFFFAOYSA-N 0.000 description 1
- PCQOPJGFSWWANK-UHFFFAOYSA-N CC1COC2=C(C=CC=C2)N1C Chemical compound CC1COC2=C(C=CC=C2)N1C PCQOPJGFSWWANK-UHFFFAOYSA-N 0.000 description 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N CCOC(=O)C(C)C Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- ZFKUGYGJZATGRG-UHFFFAOYSA-N CN1CC(C2=CC=CC=C2)OC1(C)C Chemical compound CN1CC(C2=CC=CC=C2)OC1(C)C ZFKUGYGJZATGRG-UHFFFAOYSA-N 0.000 description 1
- RMSFIZTVNLJBBO-UHFFFAOYSA-N CN1CC(C2=CC=CO2)OC1(C)C Chemical compound CN1CC(C2=CC=CO2)OC1(C)C RMSFIZTVNLJBBO-UHFFFAOYSA-N 0.000 description 1
- GRCYEAFJPWXUQL-UHFFFAOYSA-N CN1CCOC1(C)C Chemical compound CN1CCOC1(C)C GRCYEAFJPWXUQL-UHFFFAOYSA-N 0.000 description 1
- JBMZKDLFGCAZSS-UHFFFAOYSA-N CN1CCOC12CCCCC2 Chemical compound CN1CCOC12CCCCC2 JBMZKDLFGCAZSS-UHFFFAOYSA-N 0.000 description 1
- VEBLEROFGPOMPB-UHFFFAOYSA-N CNC1CC1 Chemical compound CNC1CC1 VEBLEROFGPOMPB-UHFFFAOYSA-N 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-M COC(=O)C1=CSC(C)=C1S(=O)(=O)[N-]C(=O)N1N=C(OC)N(C)C1=O.[Na+] Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)[N-]C(=O)N1N=C(OC)N(C)C1=O.[Na+] XSKZXGDFSCCXQX-UHFFFAOYSA-M 0.000 description 1
- LTNXSVURAGPHNW-UHFFFAOYSA-N COCC(=O)NC1=CC=C(O(OO)SNC(=O)C2=CC=CC=C2OC)C=C1 Chemical compound COCC(=O)NC1=CC=C(O(OO)SNC(=O)C2=CC=CC=C2OC)C=C1 LTNXSVURAGPHNW-UHFFFAOYSA-N 0.000 description 1
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
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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)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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 (fr) | 2001-09-21 | 2002-09-10 | Herbicides selectifs a base de thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)ones substituees et de phytoprotecteurs |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/010104 A-371-Of-International WO2003026427A1 (fr) | 2001-09-21 | 2002-09-10 | Herbicides selectifs a base de thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)ones substituees et de phytoprotecteurs |
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 (fr) |
EP (1) | EP1429613B1 (fr) |
JP (2) | JP4610895B2 (fr) |
KR (2) | KR100927025B1 (fr) |
CN (1) | CN1326457C (fr) |
AR (1) | AR036775A1 (fr) |
AU (1) | AU2002333811B8 (fr) |
BE (2) | BE2016C043I2 (fr) |
CA (2) | CA2460922C (fr) |
CO (1) | CO5580725A2 (fr) |
DE (2) | DE10146590A1 (fr) |
ES (1) | ES2280615T3 (fr) |
FR (2) | FR17C1034I2 (fr) |
HR (1) | HRP20040359A2 (fr) |
HU (3) | HU230218B1 (fr) |
MX (1) | MXPA04002641A (fr) |
NL (3) | NL350074I2 (fr) |
PL (1) | PL207754B1 (fr) |
PT (1) | PT1429613E (fr) |
RS (1) | RS51046B (fr) |
RU (1) | RU2308834C2 (fr) |
UA (1) | UA77010C2 (fr) |
WO (1) | WO2003026427A1 (fr) |
ZA (1) | ZA200402129B (fr) |
Cited By (4)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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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 |
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