CA2298462C - 2-benzoyl-cyclohexane-1,3-dione as herbicides - Google Patents
2-benzoyl-cyclohexane-1,3-dione as herbicides Download PDFInfo
- Publication number
- CA2298462C CA2298462C CA002298462A CA2298462A CA2298462C CA 2298462 C CA2298462 C CA 2298462C CA 002298462 A CA002298462 A CA 002298462A CA 2298462 A CA2298462 A CA 2298462A CA 2298462 C CA2298462 C CA 2298462C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- isoxazolyl
- alkyl
- ch2o
- dihydro
- 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 - Lifetime
Links
- QMNFICMPAXFAPC-UHFFFAOYSA-N 2-benzoylcyclohexane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C1C(=O)CCCC1=O QMNFICMPAXFAPC-UHFFFAOYSA-N 0.000 title claims abstract 11
- 239000004009 herbicide Substances 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- -1 cyano, thiocyanato Chemical group 0.000 claims 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 239000001301 oxygen Substances 0.000 claims 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 239000005864 Sulphur Substances 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical group O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims 2
- 239000011814 protection agent Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229940125890 compound Ia Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 241000607479 Yersinia pestis Species 0.000 abstract 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
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19734164.0 | 1997-08-07 | ||
| DE19734164 | 1997-08-07 | ||
| PCT/EP1998/004634 WO1999010327A1 (de) | 1997-08-07 | 1998-08-05 | 2-benzoyl-cyclohexan-1,3-dione als herbizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2298462A1 CA2298462A1 (en) | 1999-03-04 |
| CA2298462C true CA2298462C (en) | 2008-02-12 |
Family
ID=7838240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002298462A Expired - Lifetime CA2298462C (en) | 1997-08-07 | 1998-08-05 | 2-benzoyl-cyclohexane-1,3-dione as herbicides |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6432881B1 (https=) |
| EP (2) | EP1001938A1 (https=) |
| JP (2) | JP4592183B2 (https=) |
| AR (1) | AR016595A1 (https=) |
| AU (1) | AU9068498A (https=) |
| CA (1) | CA2298462C (https=) |
| WO (1) | WO1999010327A1 (https=) |
| ZA (1) | ZA987057B (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1001938A1 (de) * | 1997-08-07 | 2000-05-24 | Basf Aktiengesellschaft | 2-benzoyl-cyclohexan-1,3-dione als herbizide |
| DE19846792A1 (de) | 1998-10-10 | 2000-04-13 | Hoechst Schering Agrevo Gmbh | Benzoylcyclohexandione, Verfahren zur ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| MXPA02001393A (es) | 1999-08-10 | 2002-08-12 | Bayer Agrochem Kk | Herbicidas derivados de tetrazolinona. |
| DE19953136A1 (de) * | 1999-11-04 | 2001-05-10 | Aventis Cropscience Gmbh | Benzoylcyclohexandione und Benzoylpyrazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| AU784813B2 (en) | 2000-01-17 | 2006-06-29 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| JP2002080460A (ja) * | 2000-07-06 | 2002-03-19 | Nippon Bayer Agrochem Co Ltd | 除草性テトラゾール誘導体 |
| DE10043074A1 (de) | 2000-09-01 | 2002-03-14 | Aventis Cropscience Gmbh | Herbizid wirksame Benzoylcyclohexandione |
| DE10113137C2 (de) * | 2001-03-17 | 2003-05-15 | Bayer Cropscience Gmbh | Verfahren zur Herstellung von substituierten 2-Benzoyl-1,3-cyclohexandionen |
| DE10136449A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Ag | Substituierte Arylketone |
| WO2002090336A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Cropscience Ag | Substituierte arylketone |
| EP1392117B1 (en) * | 2001-05-16 | 2005-06-29 | Bayer CropScience GmbH | Herbicidal mixture comprising a benzoyl derivative, a fertilizer containing nitrogen and an adjuvant |
| PL363949A1 (en) | 2001-05-16 | 2004-11-29 | Bayer Cropscience Ag | Substituted benzoylcyclohexenones and their use as herbicidal agents |
| DE10144529A1 (de) | 2001-09-11 | 2003-03-27 | Bayer Cropscience Gmbh | 3-Aminocarbonyl substituierte Benzoylcyclohexandione |
| DE10206792A1 (de) * | 2002-02-19 | 2003-08-28 | Bayer Cropscience Ag | Substituierte Arylketone |
| DE10209645A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Ag | Substituierte Arylketone |
| DE10301110A1 (de) * | 2003-01-09 | 2004-07-22 | Bayer Cropscience Gmbh | Substituierte Benzoylderivate als Herbizide |
| DE102004029308A1 (de) * | 2004-06-17 | 2005-12-29 | Bayer Cropscience Gmbh | Substituierte Benzoylpyrazole als Herbiszide |
| DE102004029307A1 (de) * | 2004-06-17 | 2005-12-29 | Bayer Cropscience Gmbh | Substituierte Benzoylcyclohexandione als Herbizide |
| CN105399674B (zh) * | 2015-12-31 | 2017-02-15 | 青岛清原化合物有限公司 | 吡唑类化合物或其盐、制备方法、除草剂组合物及用途 |
| CN105601548A (zh) * | 2016-01-18 | 2016-05-25 | 黑龙江大学 | 苯甲酰类化合物、含有该化合物的组合物及其应用 |
| CN108264484A (zh) * | 2016-12-30 | 2018-07-10 | 浙江省化工研究院有限公司 | 一种带醚结构的取代的苯基酮类化合物、其制备方法及应用 |
| CN112142671B (zh) * | 2019-06-27 | 2024-01-16 | 东莞市东阳光农药研发有限公司 | 取代的苯甲酰-吡唑类化合物及其在农业中的应用 |
| CN112174889B (zh) * | 2019-07-03 | 2024-01-16 | 东莞市东阳光农药研发有限公司 | 取代的苯甲酰类化合物及其在农业中的应用 |
| WO2021000736A1 (zh) * | 2019-07-04 | 2021-01-07 | 东莞市东阳光农药研发有限公司 | 取代的苯甲酰-吡唑类化合物及其在农业中的应用 |
| CN112409226B (zh) * | 2019-08-23 | 2024-04-05 | 东莞市东阳光农药研发有限公司 | 取代的苯甲酰类化合物及其应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8703068D0 (en) * | 1987-02-11 | 1987-03-18 | May & Baker Ltd | Compositions of matter |
| MA21177A1 (fr) | 1987-02-11 | 1988-10-01 | May & Baker Ltd | Diones cycliques. |
| CA1340284C (en) | 1987-03-19 | 1998-12-22 | Zeneca Inc. | Herbicidal substituted cyclic diones |
| US4938796A (en) | 1987-07-06 | 1990-07-03 | Ici Americas Inc. | Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and antidotes therefor |
| DE3743695A1 (de) | 1987-12-18 | 1989-06-29 | Schering Ag | 4-benzoyl-3-hydroxy-5-oxo-3-cyclohexencarbonsaeurederivate, verfahren zur herstellung dieser verbindungen und ihre verwendung als mittel mit pflanzenwachstumsregulierender wirkung |
| JPH06271562A (ja) * | 1993-03-23 | 1994-09-27 | Hokko Chem Ind Co Ltd | シクロヘキサンジオン誘導体および除草剤 |
| JPH06321932A (ja) * | 1993-05-07 | 1994-11-22 | Hokko Chem Ind Co Ltd | シクロヘキサンジオン誘導体および除草剤 |
| HUT77009A (hu) * | 1994-11-07 | 1998-03-02 | Nippon Soda Co., Ltd. | Bicikloheptándionszármazékok és ezeket tartalmazó herbicid készítmények |
| EP1001938A1 (de) * | 1997-08-07 | 2000-05-24 | Basf Aktiengesellschaft | 2-benzoyl-cyclohexan-1,3-dione als herbizide |
-
1998
- 1998-08-05 EP EP98942611A patent/EP1001938A1/de not_active Withdrawn
- 1998-08-05 CA CA002298462A patent/CA2298462C/en not_active Expired - Lifetime
- 1998-08-05 US US09/485,231 patent/US6432881B1/en not_active Expired - Lifetime
- 1998-08-05 AU AU90684/98A patent/AU9068498A/en not_active Abandoned
- 1998-08-05 JP JP2000507656A patent/JP4592183B2/ja not_active Expired - Lifetime
- 1998-08-05 EP EP10184196A patent/EP2343276A1/de not_active Ceased
- 1998-08-05 WO PCT/EP1998/004634 patent/WO1999010327A1/de not_active Ceased
- 1998-08-06 ZA ZA9807057A patent/ZA987057B/xx unknown
- 1998-08-07 AR ARP980103923A patent/AR016595A1/es unknown
-
2010
- 2010-07-15 JP JP2010160833A patent/JP2011016803A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP4592183B2 (ja) | 2010-12-01 |
| US6432881B1 (en) | 2002-08-13 |
| ZA987057B (en) | 2000-02-07 |
| EP2343276A1 (de) | 2011-07-13 |
| AR016595A1 (es) | 2001-07-25 |
| AU9068498A (en) | 1999-03-16 |
| JP2001514171A (ja) | 2001-09-11 |
| WO1999010327A1 (de) | 1999-03-04 |
| JP2011016803A (ja) | 2011-01-27 |
| CA2298462A1 (en) | 1999-03-04 |
| EP1001938A1 (de) | 2000-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20180806 |