CA2036334C - Substituted phenylsulphonyltriazinylureas, salts thereof and agent for plant growth stimulation and inhibition based thereon - Google Patents
Substituted phenylsulphonyltriazinylureas, salts thereof and agent for plant growth stimulation and inhibition based thereonInfo
- Publication number
- CA2036334C CA2036334C CA002036334A CA2036334A CA2036334C CA 2036334 C CA2036334 C CA 2036334C CA 002036334 A CA002036334 A CA 002036334A CA 2036334 A CA2036334 A CA 2036334A CA 2036334 C CA2036334 C CA 2036334C
- Authority
- CA
- Canada
- Prior art keywords
- urea
- triazin
- dimethylamino
- compound
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 85
- 230000000638 stimulation Effects 0.000 title claims abstract description 8
- 230000008635 plant growth Effects 0.000 title claims abstract description 7
- 230000005764 inhibitory process Effects 0.000 title claims abstract description 6
- 235000013877 carbamide Nutrition 0.000 claims abstract description 28
- -1 phenylsulphonyltriazinyl ureas Chemical class 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 239000004202 carbamide Substances 0.000 claims description 132
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical class CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 22
- 229910052708 sodium Inorganic materials 0.000 claims description 16
- 239000011734 sodium Substances 0.000 claims description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- FENAOFFCBUFUEY-UHFFFAOYSA-N 1-(benzenesulfonyl)-1-(triazin-4-yl)urea Chemical class C=1C=CC=CC=1S(=O)(=O)N(C(=O)N)C1=CC=NN=N1 FENAOFFCBUFUEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 3
- 229960003975 potassium Drugs 0.000 claims 2
- 235000007686 potassium Nutrition 0.000 claims 2
- 150000003672 ureas Chemical class 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 description 70
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 230000000694 effects Effects 0.000 description 26
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 21
- 230000012010 growth Effects 0.000 description 16
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 16
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- 159000000000 sodium salts Chemical class 0.000 description 12
- 239000002689 soil Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
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- 230000002363 herbicidal effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 7
- 229940126545 compound 53 Drugs 0.000 description 7
- 238000011161 development Methods 0.000 description 7
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
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- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 6
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
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- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- HVQWYKPSNHGIDD-UHFFFAOYSA-N methyl 2-isocyanatosulfonylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)N=C=O HVQWYKPSNHGIDD-UHFFFAOYSA-N 0.000 description 3
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ODUIXUGXPFKQLG-QWRGUYRKSA-N [2-(4-chloro-2-fluoroanilino)-5-methyl-1,3-thiazol-4-yl]-[(2s,3s)-2,3-dimethylpiperidin-1-yl]methanone Chemical compound C[C@H]1[C@@H](C)CCCN1C(=O)C1=C(C)SC(NC=2C(=CC(Cl)=CC=2)F)=N1 ODUIXUGXPFKQLG-QWRGUYRKSA-N 0.000 description 2
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- 150000002500 ions Chemical class 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 230000005305 organ development Effects 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 230000002226 simultaneous effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3286/91A CH683341A5 (de) | 1990-03-07 | 1990-03-07 | Substituierte Phenylsulfonyltriazinylharnstoffe, deren Salze und Mittel zur Stimulation und Unterdrückung des Pflanzenwachstums auf deren Grundlage. |
| AU68891/91A AU631474B2 (en) | 1990-03-07 | 1990-03-07 | Substituted penylsulphonyltriazinylurea and salts thereof and means for stimulating and suppressing plant growth based on them |
| PCT/SU1990/000067 WO1991013880A1 (en) | 1990-03-07 | 1990-03-07 | Substituted penylsulphonyltriazinylurea and salts thereof and means for stimulating and suppressing plant growth based on them |
| DE4092524A DE4092524C2 (de) | 1990-03-07 | 1990-03-07 | Substituierte Phenylsulfonyltriazinylharnstoffe, deren Salze und Mittel mit pflanzenwachstumsregelierender Wirkung |
| DE19904092524 DE4092524T (enrdf_load_stackoverflow) | 1990-03-07 | 1990-03-07 | |
| JP3500742A JPH05501415A (ja) | 1990-03-07 | 1990-03-07 | 置換フェニルスルホニルトリアジニル尿素、その塩並びにそれに基づく植物成長促進及び阻害用薬剤 |
| CA002036334A CA2036334C (en) | 1990-03-07 | 1991-02-14 | Substituted phenylsulphonyltriazinylureas, salts thereof and agent for plant growth stimulation and inhibition based thereon |
| CS91442A CS44291A3 (en) | 1990-03-07 | 1991-02-20 | Agent for plant growth promoting and inhibiting |
| FR9102282A FR2673181B1 (fr) | 1990-03-07 | 1991-02-26 | Phenylsulfonyltriazinyl-urees substituees, leurs sels et produit les contenant pour stimuler et inhiber la croissance des plantes. |
| CN91102096.9A CN1064388A (zh) | 1990-03-07 | 1991-03-05 | 用于促进和抑制植物生长的制剂 |
| GB9123657A GB2251613B (en) | 1990-03-07 | 1991-11-07 | Substituted phenylsulphoryltrianzinyl ureas, salts thereof and agent for plant growth stimulation and inhibition based thereon |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/SU1990/000067 WO1991013880A1 (en) | 1990-03-07 | 1990-03-07 | Substituted penylsulphonyltriazinylurea and salts thereof and means for stimulating and suppressing plant growth based on them |
| CA002036334A CA2036334C (en) | 1990-03-07 | 1991-02-14 | Substituted phenylsulphonyltriazinylureas, salts thereof and agent for plant growth stimulation and inhibition based thereon |
| CS91442A CS44291A3 (en) | 1990-03-07 | 1991-02-20 | Agent for plant growth promoting and inhibiting |
| CN91102096.9A CN1064388A (zh) | 1990-03-07 | 1991-03-05 | 用于促进和抑制植物生长的制剂 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2036334A1 CA2036334A1 (en) | 1992-08-15 |
| CA2036334C true CA2036334C (en) | 1997-03-18 |
Family
ID=27168867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002036334A Expired - Fee Related CA2036334C (en) | 1990-03-07 | 1991-02-14 | Substituted phenylsulphonyltriazinylureas, salts thereof and agent for plant growth stimulation and inhibition based thereon |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPH05501415A (enrdf_load_stackoverflow) |
| CN (1) | CN1064388A (enrdf_load_stackoverflow) |
| AU (1) | AU631474B2 (enrdf_load_stackoverflow) |
| CA (1) | CA2036334C (enrdf_load_stackoverflow) |
| CH (1) | CH683341A5 (enrdf_load_stackoverflow) |
| CS (1) | CS44291A3 (enrdf_load_stackoverflow) |
| DE (2) | DE4092524T (enrdf_load_stackoverflow) |
| FR (1) | FR2673181B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2251613B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2040180C1 (ru) * | 1992-09-04 | 1995-07-25 | Латвийская фирма "КАРЕ" | Гербицидный синергитический состав |
| DE19963383A1 (de) | 1999-12-28 | 2001-07-05 | Aventis Cropscience Gmbh | Formulierung von Herbiziden und Pflanzenwachstumsregulatoren |
| AU4521700A (en) * | 1999-01-27 | 2000-08-18 | Aventis Cropscience Gmbh | Herbicidal formulation |
| CN105439970A (zh) * | 2015-10-16 | 2016-03-30 | 南开大学 | 一类可控土壤降解速度的磺酰脲类新结构的发现与应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1082189A (en) * | 1976-04-07 | 1980-07-22 | George Levitt | Herbicidal sulfonamides |
| DK349479A (da) * | 1978-09-27 | 1980-03-28 | Du Pont | Sulfonamidderivater og deres anvendelse til regulering af plantevaekst |
| US4231784A (en) * | 1979-05-10 | 1980-11-04 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4348219A (en) * | 1980-07-11 | 1982-09-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CS226915B1 (en) * | 1981-11-24 | 1984-04-16 | Varkonda Stefan | Plant growth regulating composition |
| US4780127A (en) * | 1982-03-25 | 1988-10-25 | Stauffer Chemical Company | Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides |
| ZA831626B (en) * | 1982-08-25 | 1983-11-30 | Velsicol Chemical Corp | New triazine compositions of matter |
| DE3322280A1 (de) * | 1983-06-16 | 1985-01-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Substituierte sulfonylharnstoffe, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und pflanzenwuchsregulierender wirkung |
| DE3413490A1 (de) * | 1984-04-10 | 1985-10-17 | Bayer Ag, 5090 Leverkusen | 2-(alkoximinoalkyloxycarbonyl)-phenylsulfonylharnstoffe |
| EP0164269B1 (en) * | 1984-06-07 | 1990-04-18 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| EP0164669B1 (de) * | 1984-06-13 | 1991-01-23 | Röhm Gmbh | Verfahren zum Überziehen von Arzneiformen |
| US4786316A (en) * | 1984-07-13 | 1988-11-22 | E. I. Du Pont De Nemours And Company | Herbicidal ortho-sulfamoyl sulfonamides |
| AU611191B2 (en) * | 1987-07-27 | 1991-06-06 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| ES2058502T3 (es) * | 1988-03-24 | 1994-11-01 | Du Pont | Fluoroalcoxiaminotriazinas para el control de las malas hierbas en la remolacha azucarera. |
| JP2738010B2 (ja) * | 1988-07-15 | 1998-04-08 | 日産化学工業株式会社 | ピラゾール誘動体及び選択性除草剤 |
| JP2764931B2 (ja) * | 1988-08-05 | 1998-06-11 | 日産化学工業株式会社 | 安息香酸類の製法 |
-
1990
- 1990-03-07 DE DE19904092524 patent/DE4092524T/de active Pending
- 1990-03-07 JP JP3500742A patent/JPH05501415A/ja active Pending
- 1990-03-07 CH CH3286/91A patent/CH683341A5/de not_active IP Right Cessation
- 1990-03-07 AU AU68891/91A patent/AU631474B2/en not_active Ceased
- 1990-03-07 DE DE4092524A patent/DE4092524C2/de not_active Expired - Fee Related
-
1991
- 1991-02-14 CA CA002036334A patent/CA2036334C/en not_active Expired - Fee Related
- 1991-02-20 CS CS91442A patent/CS44291A3/cs unknown
- 1991-02-26 FR FR9102282A patent/FR2673181B1/fr not_active Expired - Fee Related
- 1991-03-05 CN CN91102096.9A patent/CN1064388A/zh active Pending
- 1991-11-07 GB GB9123657A patent/GB2251613B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2036334A1 (en) | 1992-08-15 |
| FR2673181A1 (fr) | 1992-08-28 |
| GB2251613B (en) | 1993-11-17 |
| JPH05501415A (ja) | 1993-03-18 |
| DE4092524T (enrdf_load_stackoverflow) | 1992-04-23 |
| AU631474B2 (en) | 1992-11-26 |
| GB2251613A (en) | 1992-07-15 |
| CS44291A3 (en) | 1992-12-16 |
| CN1064388A (zh) | 1992-09-16 |
| GB9123657D0 (en) | 1992-01-02 |
| AU6889191A (en) | 1991-10-10 |
| FR2673181B1 (fr) | 1994-02-11 |
| DE4092524C2 (de) | 1996-09-12 |
| CH683341A5 (de) | 1994-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |