DD250708A5 - Verfahren zur herstellung von n-(3-chlor-1,2,4-oxidiazol-5-yl)-harnstoffen der allgemeinen formel (i) - Google Patents

Verfahren zur herstellung von n-(3-chlor-1,2,4-oxidiazol-5-yl)-harnstoffen der allgemeinen formel (i) Download PDF

Info

Publication number: DD250708A5
Authority: DD; German Democratic Republic
Prior art keywords: chloro; formula; general formula; oxadiazol; process according
Prior art date: 1984-12-12

Application number

DD85296263A

Other languages

German (de)

English (en)

Inventor

Ulrich Heinemann

Hans-Joachim Knops

Karl Steinbeck

Wilhelm Brandes

Gerd Haenssler

Paul Reinecke

Original Assignee

Bayer Ag,De

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.)

1984-12-12

Filing date

1985-12-10

Publication date

1987-10-21

1985-12-10 Application filed by Bayer Ag,De filed Critical Bayer Ag,De

1987-10-21 Publication of DD250708A5 publication Critical patent/DD250708A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 17
108010046334 Urease Proteins 0.000 title 1
-1 3-chloro-1,2,4-oxadiazol-5-yl Chemical group 0.000 claims abstract description 23
ASMIZOGDJKBDKV-UHFFFAOYSA-N 3-chloro-1,2,4-oxadiazol-5-amine Chemical compound NC1=NC(Cl)=NO1 ASMIZOGDJKBDKV-UHFFFAOYSA-N 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 8
239000012948 isocyanate Substances 0.000 abstract description 6
150000002513 isocyanates Chemical class 0.000 abstract description 6
239000003054 catalyst Substances 0.000 abstract description 5
239000000417 fungicide Substances 0.000 abstract description 4
239000000575 pesticide Substances 0.000 abstract description 3
239000002562 thickening agent Substances 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
239000012973 diazabicyclooctane Substances 0.000 description 2
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
239000012990 dithiocarbamate Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000003949 imides Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
XYUCULXRVSQDCG-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-isocyanatobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(N=C=O)C(Cl)=C1Cl XYUCULXRVSQDCG-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
BLYIYKMHZBWIDJ-UHFFFAOYSA-N 2,5-dichloro-3h-1,2,4-oxadiazole Chemical compound ClN1CN=C(Cl)O1 BLYIYKMHZBWIDJ-UHFFFAOYSA-N 0.000 description 1
CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000760356 Chytridiomycetes Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000233654 Oomycetes Species 0.000 description 1
241001503460 Plasmodiophorida Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- 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)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD85296263A 1984-12-12 1985-12-10 Verfahren zur herstellung von n-(3-chlor-1,2,4-oxidiazol-5-yl)-harnstoffen der allgemeinen formel (i) DD250708A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843445205 DE3445205A1 (de)	1984-12-12	1984-12-12	N-(3-chlor-1,2,4-oxadiazol-5-yl)-harnstoffe

Publications (1)

Publication Number	Publication Date
DD250708A5 true DD250708A5 (de)	1987-10-21

Family

ID=6252505

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD85296263A DD250708A5 (de)	1984-12-12	1985-12-10	Verfahren zur herstellung von n-(3-chlor-1,2,4-oxidiazol-5-yl)-harnstoffen der allgemeinen formel (i)
DD85284061A DD241544A5 (de)	1984-12-12	1985-12-10	Schaedlingsbekaempfungsmittel

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD85284061A DD241544A5 (de)	1984-12-12	1985-12-10	Schaedlingsbekaempfungsmittel

Country Status (12)

Country	Link
US (1)	US4642312A (da)
EP (1)	EP0185983A1 (da)
JP (1)	JPS61140574A (da)
CN (1)	CN85108862A (da)
BR (1)	BR8506194A (da)
DD (2)	DD250708A5 (da)
DE (1)	DE3445205A1 (da)
DK (1)	DK573085A (da)
ES (1)	ES8704912A1 (da)
HU (1)	HUT39974A (da)
PT (1)	PT81588B (da)
ZA (1)	ZA859515B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3640153A1 (de) *	1986-11-25	1988-05-26	Bayer Ag	Chlor-1,2,4-oxadiazole
CN111601802A (zh)	2017-11-28	2020-08-28	拜耳股份有限公司	作为杀虫剂的杂环化合物

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3221005A (en) *	1962-08-30	1965-11-30	Eastman Kodak Co	Azo dyes from 5-amino-1,2,4-thiadiazoles
US3822280A (en) *	1971-03-11	1974-07-02	Ciba Geigy Corp	Certain diazolyl ureas
DE2054342A1 (de) *	1970-11-05	1972-05-10	Farbenfabriken Bayer Ag, 5090 Leverkusen	Neue 1,2,4-Oxdiazole
DE2801509A1 (de) *	1978-01-12	1979-07-19	Schering Ag	1,2,4-oxadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel
EP0111442A1 (de) *	1982-11-12	1984-06-20	Ciba-Geigy Ag	N-2-Heterocyclyl-phenylsulfonyl-N'-pyrimidinyl- und -triazinyl-harnstoffe

1984
- 1984-12-12 DE DE19843445205 patent/DE3445205A1/de not_active Withdrawn
1985
- 1985-11-25 US US06/801,452 patent/US4642312A/en not_active Expired - Fee Related
- 1985-12-02 PT PT81588A patent/PT81588B/pt unknown
- 1985-12-03 EP EP85115352A patent/EP0185983A1/de not_active Withdrawn
- 1985-12-05 CN CN198585108862A patent/CN85108862A/zh active Pending
- 1985-12-10 DD DD85296263A patent/DD250708A5/de unknown
- 1985-12-10 DD DD85284061A patent/DD241544A5/de unknown
- 1985-12-11 BR BR8506194A patent/BR8506194A/pt unknown
- 1985-12-11 ES ES549839A patent/ES8704912A1/es not_active Expired
- 1985-12-11 DK DK573085A patent/DK573085A/da not_active Application Discontinuation
- 1985-12-11 HU HU854738A patent/HUT39974A/hu unknown
- 1985-12-11 JP JP60277097A patent/JPS61140574A/ja active Pending
- 1985-12-12 ZA ZA859515A patent/ZA859515B/xx unknown

Also Published As

Publication number	Publication date
JPS61140574A (ja)	1986-06-27
CN85108862A (zh)	1986-07-30
BR8506194A (pt)	1986-08-26
DE3445205A1 (de)	1986-06-12
ZA859515B (en)	1986-08-27
EP0185983A1 (de)	1986-07-02
DK573085D0 (da)	1985-12-11
ES549839A0 (es)	1987-04-16
ES8704912A1 (es)	1987-04-16
PT81588A (en)	1986-01-01
DD241544A5 (de)	1986-12-17
PT81588B (en)	1987-10-16
DK573085A (da)	1986-06-13
HUT39974A (en)	1986-11-28
US4642312A (en)	1987-02-10

Publication	Publication Date	Title
EP0334135A2 (de)	1989-09-27	Trisubstituierte 1,3,5-Triazin-2,4,6-trione
EP0106243B1 (de)	1986-05-28	Azolyl-methylamine, ihre Herstellung und Verwendung in mikrobiziden Mitteln
EP0037971B1 (de)	1983-12-21	Trisubstituierte Cyanguanidine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
DE3433391A1 (de)	1986-03-20	Acylierte saccharin-derivate
DE2206011A1 (de)	1973-08-23	1-acyl-3-aminosulfonyl-2-imino-benzimidazoline, verfahren zu ihrer herstellung und ihre fungizide verwendung
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