NL8002020A - N-gesubstitueerde tetrahydrofthalimiden en op de toepassing hiervan als herbicidale verbinding. - Google Patents

N-gesubstitueerde tetrahydrofthalimiden en op de toepassing hiervan als herbicidale verbinding. Download PDF

Info

Publication number: NL8002020A
Authority: NL; Netherlands
Prior art keywords: substituted; group; formula; carbon atoms; tetrahydrophthalimides
Prior art date: 1979-04-13

Application number

NL8002020A

Other languages

English (en)

Dutch (nl)

Original Assignee

Mitsubishi Chem Ind

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.)

1979-04-13

Filing date

1980-04-04

Publication date

1980-10-15

1979-04-13 Priority claimed from JP4495179A external-priority patent/JPS55139305A/ja

1979-04-13 Priority claimed from JP4494879A external-priority patent/JPS55139359A/ja

1980-04-04 Application filed by Mitsubishi Chem Ind filed Critical Mitsubishi Chem Ind

1980-10-15 Publication of NL8002020A publication Critical patent/NL8002020A/nl

Links

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239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002194 fatty esters Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
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 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000009165 saligot Nutrition 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000009331 sowing Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
238000012546 transfer Methods 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/32—Cyclic imides of polybasic carboxylic acids or 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Indole Compounds (AREA)

NL8002020A 1979-04-13 1980-04-04 N-gesubstitueerde tetrahydrofthalimiden en op de toepassing hiervan als herbicidale verbinding. NL8002020A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP4495179		1979-04-13
JP4494879		1979-04-13
JP4495179A JPS55139305A (en)	1979-04-13	1979-04-13	Herbicide
JP4494879A JPS55139359A (en)	1979-04-13	1979-04-13	Tetrahydrophthalimides, and herbicide containing compound as effective component

Publications (1)

Publication Number	Publication Date
NL8002020A true NL8002020A (nl)	1980-10-15

Family

ID=26384912

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8002020A NL8002020A (nl)	1979-04-13	1980-04-04	N-gesubstitueerde tetrahydrofthalimiden en op de toepassing hiervan als herbicidale verbinding.

Country Status (9)

Country	Link
US (1)	US4292070A (de)
BR (1)	BR8002295A (de)
CA (1)	CA1109881A (de)
CH (1)	CH646424A5 (de)
DE (1)	DE3013162A1 (de)
FR (1)	FR2453852A1 (de)
GB (1)	GB2046754B (de)
IT (1)	IT1149914B (de)
NL (1)	NL8002020A (de)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU542544B2 (en) *	1980-03-12	1985-02-28	Nippon Kayaku Kabushiki Kaisha	Tetrahydrophthalimide derivatives
EP0049511A1 (de) *	1980-10-07	1982-04-14	Mitsubishi Kasei Corporation	Tetrahydrophthalimide und herbizide Zusammensetzungen
US4536209A (en) *	1980-10-07	1985-08-20	Mitsubishi Chemical Industries Ltd.	N-(3-substituted oxyphenyl)tetrahydrophthalimides and herbicidal composition
US4431822A (en) *	1981-03-30	1984-02-14	Sumitomo Chemical Company, Limited	Tetrahydrophthalimides, and their production and use
AU550845B2 (en) *	1981-03-30	1986-04-10	Sumitomo Chemical Company, Limited	Tetrahydrophthalimides and their starting compounds
US5191105A (en) *	1981-09-01	1993-03-02	Sumitomo Chemical Company, Ltd.	Tetrahydrophthalimides, and their production and use as herbicides
US4484941A (en) *	1981-09-01	1984-11-27	Sumitomo Chemical Company, Limited	Tetrahydrophthalimides, and their production and use as herbicides
US4484940A (en) *	1981-09-01	1984-11-27	Sumitomo Chemical Company, Limited	Tetrahydrophthalimides, and their production and use as herbicides
AU557324B2 (en) *	1981-12-25	1986-12-18	Sumitomo Chemical Company, Limited	Tetrahydro phthalimide compounds
DE3377646D1 (en) *	1982-05-26	1988-09-15	Sumitomo Chemical Co	Tetrahydrophthalimides, and their production and use
JPS59212472A (ja) *	1983-05-16	1984-12-01	Sumitomo Chem Co Ltd	４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル−１，３−ジオン誘導体、その製造法およびそれを有効成分とする除草剤
US4902832A (en) *	1983-08-31	1990-02-20	Sumitomo Chemical Company, Limited	2-Substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones, and their production and use
JPS6054362A (ja) *	1983-08-31	1985-03-28	Sumitomo Chem Co Ltd	テトラヒドロフタルイミド誘導体，その製造法およびそれを有効成分とする除草剤
US4563535A (en) *	1983-09-19	1986-01-07	Sumitomo Chemical Co., Ltd.	Process for producing tetrahydrophthalimides
DE3533442A1 (de) *	1985-09-19	1987-03-26	Hoechst Ag	Neue 2-aryl-4,5,6,7-tetrahydroisoindolinone, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz
US4846882A (en) *	1986-01-10	1989-07-11	Fmc Corporation	Herbicidal aryl tetrahydrophthalimides
IT1201113B (it) *	1986-01-10	1989-01-27	Fmc Corp	Composti erbicidi
EP0259265B1 (de) *	1986-09-03	1991-09-11	Ciba-Geigy Ag	3-Methylphthalimide
EP0259264A1 (de) *	1986-09-03	1988-03-09	Ciba-Geigy Ag	Neue 4-Methylphthalimide
JPS63225306A (ja) *	1986-10-09	1988-09-20	Sumitomo Chem Co Ltd	除草組成物
US4816065A (en) *	1986-12-23	1989-03-28	Fmc Corporation	Herbicides
US4885025A (en) *	1986-12-23	1989-12-05	Fmc Corporation	Herbicidal tetrazolinones and use thereof
DE3712987A1 (de) *	1987-04-16	1988-11-10	Bayer Ag	N-arylpyrrolin-2,5-dione
DE3724399A1 (de) *	1987-07-23	1989-02-02	Basf Ag	Phenylalkenylcarbonsaeuren und deren ester
US4919704A (en) *	1987-08-14	1990-04-24	Ciba-Geigy Corporation	4,5,6,7-Tetrahydroisoindole-1,3-diones
DE3736297A1 (de) *	1987-10-27	1989-05-11	Basf Ag	N-phenyltetrahydrophthalimidverbindungen
US5169428A (en) *	1987-12-30	1992-12-08	Tosoh Corporation	Tetrahydrophthalimide derivative and herbicide composition containing same
EP0323271A1 (de) *	1987-12-30	1989-07-05	Tosoh Corporation	Tetrahydrophthalimid-Derivate und dieses enthaltende Herbizide
US5221318A (en) *	1988-10-15	1993-06-22	Bayer Aktiengesellschaft	Herbicidal N-aryl-substituted nitrogen-containing heterocycles
DE3835168A1 (de) *	1988-10-15	1990-04-19	Bayer Ag	N-aryl-stickstoffheterocyclen, mehrere verfahren zu ihrer herstellung und ihre verwendung als herbizide
DE3905916A1 (de) *	1989-02-25	1990-08-30	Basf Ag	Verwendung von derivaten des n-phenyl-3,4,5,6-tetrahydrophthalimids zur desikkation und abszission von pflanzenorganen
USRE37664E1 (en) *	1989-02-25	2002-04-16	Basf Aktiengessellschaft	Use of derivatives of N-phenl-3,4,5,6-tetrahydrophthalimide for the desiccation and abscission of plant organs
JP2860367B2 (ja) *	1989-03-02	1999-02-24	アグロカネショウ株式会社	複素環化合物、その製造法及びそれを有効成分として含有する除草剤
CA2066203A1 (en) *	1990-07-17	1992-01-18	Kenji Hirai	Benzene derivatives substituted with heterocyclic ring, process for preparing same, and herbicides containing same as active ingredients

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3745170A (en) *	1969-03-19	1973-07-10	Sumitomo Chemical Co	Novel n-(3,5-dihalophenyl)-imide compounds
US3654302A (en) *	1970-01-30	1972-04-04	Herbert Schwartz	Tetrahydrophthalanils
US3878224A (en) *	1970-12-23	1975-04-15	Mitsubishi Chem Ind	N-substituted-{66 {40 -tetrahydrophthalimides
US3984435A (en) *	1970-12-23	1976-10-05	Mitsubishi Chemical Industries Ltd.	Herbicidal N-substituted-Δ1 -tetrahydrophthalimide
DE2165651C2 (de) *	1971-10-14	1982-07-08	Mitsubishi Chemical Industries, Ltd., Tokyo	N-Substituierte Δ↑1↑-Tetrahydrophthalimide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Herbizide
US4001272A (en) *	1974-09-03	1977-01-04	E. I. Du Pont De Nemours And Company	Herbicidal 2-fluoro-4-halo-phenyl-4,5,6,7-tetrahydro-2h-isoindole-1,3-diones
US4032326A (en) *	1974-12-24	1977-06-28	E. I. Du Pont De Nemours And Company	Herbicidal 2-substituted aryl-4,5,6,7-tetrahydro-2h-isoindole-1,3-diones

1980
- 1980-03-24 US US06/133,270 patent/US4292070A/en not_active Expired - Lifetime
- 1980-04-03 DE DE19803013162 patent/DE3013162A1/de not_active Withdrawn
- 1980-04-04 NL NL8002020A patent/NL8002020A/nl not_active Application Discontinuation
- 1980-04-11 CA CA349,621A patent/CA1109881A/en not_active Expired
- 1980-04-11 IT IT21339/80A patent/IT1149914B/it active
- 1980-04-11 CH CH282280A patent/CH646424A5/de not_active IP Right Cessation
- 1980-04-14 FR FR8008326A patent/FR2453852A1/fr active Granted
- 1980-04-14 BR BR8002295A patent/BR8002295A/pt unknown
- 1980-04-14 GB GB8012274A patent/GB2046754B/en not_active Expired

Also Published As

Publication number	Publication date
GB2046754B (en)	1983-03-16
DE3013162A1 (de)	1980-10-30
US4292070A (en)	1981-09-29
CA1109881A (en)	1981-09-29
IT1149914B (it)	1986-12-10
CH646424A5 (de)	1984-11-30
FR2453852B1 (de)	1983-07-08
GB2046754A (en)	1980-11-19
BR8002295A (pt)	1980-12-02
FR2453852A1 (fr)	1980-11-07
IT8021339A0 (it)	1980-04-11

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1986-12-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US4292070A (en)	1981-09-29	N-Substituted tetrahydrophthalimide and herbicidal composition
US4929273A (en)	1990-05-29	N-benzyl-2-(4-fluoro-3-trifluoromethylphenoxy)butanoic amide and herbicidal composition containing the same
CZ279697B6 (cs)	1995-06-14	Tetrahydroftalimidové sloučeniny, způsob jejich výroby a herbicidní prostředek na jejich bázi
NL8000888A (nl)	1980-08-26	Heterocyclische etherachtige fenoxy-vetzure derivaten, de toepassing als herbicide en een werkwijze voor de bereiding van de fenoxy-vetzure derivaten.
US4709049A (en)	1987-11-24	2-substituted phenyl-4,5,6,7,-tetrahydro-2H-indole-1,3,-diones, and their production and use
US4001272A (en)	1977-01-04	Herbicidal 2-fluoro-4-halo-phenyl-4,5,6,7-tetrahydro-2h-isoindole-1,3-diones
US4032326A (en)	1977-06-28	Herbicidal 2-substituted aryl-4,5,6,7-tetrahydro-2h-isoindole-1,3-diones
EP0046467B1 (de)	1985-03-27	Chinoxalinderivate und herbizide Zusammensetzung
US4752325A (en)	1988-06-21	2-substituted phenyl-3-chlorotetrahydro-2H-indazoles composition containing them, and herbicidal method of using them
US5252536A (en)	1993-10-12	Substituted indolinones useful as herbicidal agents
US4695312A (en)	1987-09-22	4,5,6,7-tetrahydro-2H-indazole derivatives and herbicides containing them
CN1043642C (zh)	1999-06-16	除草的吡咯并吡啶化合物,包含它们的除草组合物及用途
US4670042A (en)	1987-06-02	Tetrahydrophthalimides, and their production and use as herbicides
EP0049511A1 (de)	1982-04-14	Tetrahydrophthalimide und herbizide Zusammensetzungen
EP0493606B1 (de)	2000-10-18	Heterocyclisch substituiertes benzolderivat, dessen darstellung und herbizid, welches dieses als wirkstoff enthält
US5076835A (en)	1991-12-31	Aryloxyspiroalkylindolinone herbicides
US4608080A (en)	1986-08-26	Herbicidal 2-phenyl-4,5,6,7-tetrahydro-2H-indazoles
KR900001185B1 (ko)	1990-02-27	치환 이미다졸리닐 벤조산, 에스테르 및 염의 제조 방법
US5182397A (en)	1993-01-26	Aryloxyspiroalkylindolinone herbicides
EP0095192A2 (de)	1983-11-30	Tetrahydrophthalimide, Herstellung und Anwendung
US6197728B1 (en)	2001-03-06	Quinoxaline derivatives and herbicidal composition
USH531H (en)	1988-10-04	Anilide herbicide derivatives
US4902832A (en)	1990-02-20	2-Substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones, and their production and use
EP0122130B1 (de)	1989-09-06	Herbizid wirksame Tetrahydrobenzothiazol-Derivate
CA1250843A (en)	1989-03-07	Quinoxaline and their production