JPS6270357A - 新規なテトラヒドロイソインドリノン、それらの製造方法およびそれらを含有する除草剤 - Google Patents

新規なテトラヒドロイソインドリノン、それらの製造方法およびそれらを含有する除草剤

Info

Publication number: JPS6270357A
Authority: JP; Japan
Prior art keywords: alkyl; alkoxy; halogen; formula; phenyl
Prior art date: 1985-09-19
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.): Pending

Application number

JP21825786A

Other languages

English (en)

Japanese (ja)

Inventor

ライネル・リーブル

ラインハルト・ハントテ

ヒルマール・ミルデンベルゲル

クラウス・バウエル

ヘルマン・ビーリンゲル

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.)

Hoechst AG

Original Assignee

Hoechst 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.)

1985-09-19

Filing date

1986-09-18

Publication date

1987-03-31

1986-09-18 Application filed by Hoechst AG filed Critical Hoechst AG

1987-03-31 Publication of JPS6270357A publication Critical patent/JPS6270357A/ja

Status Pending legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title claims description 5
239000004009 herbicide Substances 0.000 title claims description 4
KOJMPALATKWNPR-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydroisoindol-1-one Chemical class C1CCC=C2C(=O)NCC21 KOJMPALATKWNPR-UHFFFAOYSA-N 0.000 title description 3
229910052736 halogen Inorganic materials 0.000 claims description 54
150000002367 halogens Chemical class 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 51
239000000126 substance Substances 0.000 claims description 49
150000001875 compounds Chemical class 0.000 claims description 41
238000006467 substitution reaction Methods 0.000 claims description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
-1 phenylthio, phenylsulfinyl Chemical group 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000004414 alkyl thio group Chemical group 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 11
125000003302 alkenyloxy group Chemical group 0.000 claims description 9
125000005133 alkynyloxy group Chemical group 0.000 claims description 9
150000001768 cations Chemical class 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 51
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 28
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 6
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
125000004429 atom Chemical group 0.000 claims 3
125000000000 cycloalkoxy group Chemical group 0.000 claims 3
229910052794 bromium Inorganic materials 0.000 claims 2
125000004093 cyano group Chemical group *C#N 0.000 claims 2
244000045561 useful plants Species 0.000 claims 1
241000196324 Embryophyta Species 0.000 description 29
239000013543 active substance Substances 0.000 description 22
239000000203 mixture Substances 0.000 description 16
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
239000013078 crystal Substances 0.000 description 11
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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238000002844 melting Methods 0.000 description 8
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239000003795 chemical substances by application Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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238000006243 chemical reaction Methods 0.000 description 5
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239000011591 potassium Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
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241000192043 Echinochloa Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241001148683 Zostera marina Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
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238000000354 decomposition reaction Methods 0.000 description 3
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239000003337 fertilizer Substances 0.000 description 3
239000012634 fragment Substances 0.000 description 3
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NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
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239000002244 precipitate Substances 0.000 description 3
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ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 2
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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 description 2
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QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
OZYJVQJGKRFVHQ-UHFFFAOYSA-L dipotassium trioxidophosphanium Chemical compound [K+].[K+].[O-]P([O-])=O OZYJVQJGKRFVHQ-UHFFFAOYSA-L 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
VGYFVNQYBUPXCQ-UHFFFAOYSA-N ethene;2-methyloxirane Chemical group C=C.CC1CO1 VGYFVNQYBUPXCQ-UHFFFAOYSA-N 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
241001233957 eudicotyledons Species 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
201000007647 intestinal volvulus Diseases 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
RVPVRDXYQKGNMQ-UHFFFAOYSA-N lead(2+) Chemical compound [Pb+2] RVPVRDXYQKGNMQ-UHFFFAOYSA-N 0.000 description 1
HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012875 nonionic emulsifier Substances 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
125000005541 phosphonamide group Chemical group 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
229920001522 polyglycol ester Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
235000003513 sheep sorrel Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Indole Compounds (AREA)

JP21825786A 1985-09-19 1986-09-18 新規なテトラヒドロイソインドリノン、それらの製造方法およびそれらを含有する除草剤 Pending JPS6270357A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE3533370		1985-09-19
DE3533370.7		1985-09-19
DE3604599.3		1986-02-14

Publications (1)

Publication Number	Publication Date
JPS6270357A true JPS6270357A (ja)	1987-03-31

Family

ID=6281345

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP21825786A Pending JPS6270357A (ja)	1985-09-19	1986-09-18	新規なテトラヒドロイソインドリノン、それらの製造方法およびそれらを含有する除草剤

Country Status (3)

Country	Link
JP (1)	JPS6270357A (de)
DD (1)	DD249622A5 (de)
ZA (1)	ZA867106B (de)

1986
- 1986-09-18 DD DD29452486A patent/DD249622A5/de unknown
- 1986-09-18 ZA ZA867106A patent/ZA867106B/xx unknown
- 1986-09-18 JP JP21825786A patent/JPS6270357A/ja active Pending

Also Published As

Publication number	Publication date
ZA867106B (en)	1987-04-29
DD249622A5 (de)	1987-09-16

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JP2558516B2 (ja)	1996-11-27	ピリミジン誘導体及び除草剤
JPS62174059A (ja)	1987-07-30	ピリミジン誘導体および除草剤
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JP2012528108A (ja)	2012-11-12	殺菌剤としての置換キナゾリン
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KR20170029528A (ko)	2017-03-15	제초 피리다지논 유도체
JPH05194492A (ja)	1993-08-03	除草剤及び植物成長制御剤としてのピリジルスルホニル尿素化合物の塩類、それらの製造及びそれらの利用方法
JPS63166880A (ja)	1988-07-11	二環式イミド、それらの製造方法およびそれらを含有する除草剤
JPH0435462B2 (de)	1992-06-11
JPH04145081A (ja)	1992-05-19	ピラゾールカルボン酸誘導体及び除草剤
AU596174B2 (en)	1990-04-26	Fungicidal pyridyl cyclopropane carboxamides
EP0271975B1 (de)	1992-06-24	3-Perfluoroalkyl-isoxazol-5-yl-oxycarbonsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
US4886542A (en)	1989-12-12	Herbicide compositions of N-(phosphonomethylglycyl) sulfonylamines and process for using same
US4767772A (en)	1988-08-30	Fungicidal pyridyl cyclopropane carboximides
JPS6270356A (ja)	1987-03-31	新規な２−アリ−ル−４、５、６、７−テトラヒドロイソインドリノン、それらの製造方法およびそれらを含有する除草剤
US4766135A (en)	1988-08-23	Fungicidal N-(substituted thio)-pyridyl cyclopropane carboxamides
JPS6344122B2 (de)	1988-09-02
JPH0436284A (ja)	1992-02-06	ジフェニルフロピリミジン誘導体、その製造法およびそれを有効成分とする除草剤
JPH0363266A (ja)	1991-03-19	アラルキルアミン誘導体、その製法及び殺菌、殺虫剤
JPH03193765A (ja)	1991-08-23	アルカン酸誘導体及び除草剤
JPS6025404B2 (ja)	1985-06-18	除草剤
JP2779720B2 (ja)	1998-07-23	ピコリン酸誘導体及び除草剤
JPS58140091A (ja)	1983-08-19	樹脂酸−スズ複合体とそれを含有する殺虫、殺菌剤
JPS58219167A (ja)	1983-12-20	置換フェニルヒダントイン誘導体およびそれを有効成分とする除草剤
KR830002894B1 (ko)	1983-12-30	피리다진 유도체의 제조방법