CA1262143A - Derives de formylglycine - Google Patents

Derives de formylglycine

Info

Publication number: CA1262143A
Authority: CA; Canada
Prior art keywords: cooch3; cooc; formula; cooc2h5; plants
Prior art date: 1984-10-16
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

Application number

CA000596667A

Other languages

English (en)

Inventor

Robert W. Lang

Pierre Martin

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.)

Ciba Geigy Investments Ltd

Original Assignee

Ciba Geigy 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.)

1984-10-16

Filing date

1989-04-13

Publication date

1989-10-03

1985-10-11 Priority claimed from CA000492846A external-priority patent/CA1256442A/fr

1989-04-13 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1989-04-13 Priority to CA000596667A priority Critical patent/CA1262143A/fr

1989-10-03 Application granted granted Critical

1989-10-03 Publication of CA1262143A publication Critical patent/CA1262143A/fr

Status Expired legal-status Critical Current

Links

UGJBHEZMOKVTIM-UHFFFAOYSA-N N-formylglycine Chemical class OC(=O)CNC=O UGJBHEZMOKVTIM-UHFFFAOYSA-N 0.000 title claims abstract description 7
-1 C1-C4-alkoxycarbonyl Chemical group 0.000 claims abstract description 23
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 20
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
239000000460 chlorine Substances 0.000 claims abstract description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052794 bromium Chemical group 0.000 claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
125000006418 4-methylphenylsulfonyl group Chemical group 0.000 claims abstract description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 3
229920002554 vinyl polymer Polymers 0.000 claims abstract description 3
241000233866 Fungi Species 0.000 abstract description 12
230000003032 phytopathogenic effect Effects 0.000 abstract description 7
150000005358 3-phenylpyrroles Chemical class 0.000 abstract description 5
239000000543 intermediate Substances 0.000 abstract description 5
230000003641 microbiacidal effect Effects 0.000 abstract description 4
241000607479 Yersinia pestis Species 0.000 abstract 1
239000000203 mixture Substances 0.000 description 40
150000001875 compounds Chemical class 0.000 description 39
241000196324 Embryophyta Species 0.000 description 32
239000004480 active ingredient Substances 0.000 description 23
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
239000013543 active substance Substances 0.000 description 19
239000000243 solution Substances 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
239000004094 surface-active agent Substances 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
235000013399 edible fruits Nutrition 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
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125000000217 alkyl group Chemical group 0.000 description 8
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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 8
239000003921 oil Substances 0.000 description 8
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239000002202 Polyethylene glycol Substances 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
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239000007788 liquid Substances 0.000 description 7
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229920001223 polyethylene glycol Polymers 0.000 description 7
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239000000047 product Substances 0.000 description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
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239000008187 granular material Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
241000894006 Bacteria Species 0.000 description 4
235000016068 Berberis vulgaris Nutrition 0.000 description 4
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
208000031888 Mycoses Diseases 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
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230000002349 favourable effect Effects 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000002156 mixing Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000002689 soil Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
244000291564 Allium cepa Species 0.000 description 3
235000002732 Allium cepa var. cepa Nutrition 0.000 description 3
241001465180 Botrytis Species 0.000 description 3
244000025254 Cannabis sativa Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
206010061217 Infestation Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
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239000002585 base Substances 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003240 coconut oil Substances 0.000 description 3
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150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000005457 ice water Substances 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000003223 protective agent Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
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DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
LJDRAKFYYGCAQC-UHFFFAOYSA-N 3-phenyl-1h-pyrrole Chemical class N1C=CC(C=2C=CC=CC=2)=C1 LJDRAKFYYGCAQC-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
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FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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229960000391 sorbitan trioleate Drugs 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003760 tallow Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000596667A 1984-10-16 1989-04-13 Derives de formylglycine Expired CA1262143A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000596667A CA1262143A (fr)	1984-10-16	1989-04-13	Derives de formylglycine

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH494984		1984-10-16
CH4949/84-9		1984-10-16
CA000492846A CA1256442A (fr)	1984-10-16	1985-10-11	Derives de 3-phenylpyrroles
CA000596667A CA1262143A (fr)	1984-10-16	1989-04-13	Derives de formylglycine

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000492846A Division CA1256442A (fr)	1984-10-16	1985-10-11	Derives de 3-phenylpyrroles

Publications (1)

Publication Number	Publication Date
CA1262143A true CA1262143A (fr)	1989-10-03

Family

ID=25670805

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000596667A Expired CA1262143A (fr)	1984-10-16	1989-04-13	Derives de formylglycine

Country Status (1)

Country	Link
CA (1)	CA1262143A (fr)

1989
- 1989-04-13 CA CA000596667A patent/CA1262143A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1993-04-04	MKLA	Lapsed

Publication	Publication Date	Title
US4822919A (en)	1989-04-18	Novel production processes
EP0206999B1 (fr)	1991-08-14	Substance microbicide
EP0172786B1 (fr)	1991-01-30	Dérivés de pyrimidine actifs comme parasiticides
EP0126254B1 (fr)	1987-11-11	Dérivés de N-(2-nitrophényl)-4-aminopyrimidine comme microbicides
JP2632187B2 (ja)	1997-07-23	アニリノピリミジン誘導体、その組成物、それらの製造方法及び有害生物防除方法
EP0139613A1 (fr)	1985-05-02	Dérivés de la N-(nitro-2 phényl) amino-4 pyrimidine, leur préparation et leur application
EP0135472A2 (fr)	1985-03-27	Dérivés de N-(2-nitrophényl)-2-aminopyrimidine, leur préparation et leur usage
PL156233B1 (en)	1992-02-28	Agent for fighting against harmflul insects or microorganisms or preventing an injurious attack by them
JPS63162680A (ja)	1988-07-06	オキサジアゾール誘導体およびそれを含む有害生物防除剤組成物
US4868202A (en)	1989-09-19	Pesticidal compositions containing 3-phenylpyrrole derivatives
EP0198797B1 (fr)	1990-01-31	Parasiticide
EP0133247B1 (fr)	1989-12-13	Dérivés de N-aminométhyl-3-phényl-4-cyanopyrrole, leur préparation et leur utilisation comme microbicide
EP0310558A2 (fr)	1989-04-05	Agent microbicide
EP0130149B1 (fr)	1989-04-12	Dérivés de 3-phényl-4-cyanopyrrol, procédé de préparation et utilisation comme microbicides
US4778901A (en)	1988-10-18	Intermediates for the preparation of microficidal pyrroline derivatives and conversion of same to phytofungicidal pyrrole derivatives
FI112215B (fi)	2003-11-14	(4-syklopropyyli-6-metyyli-pyrimidin-2-yyli)-fenyyli-amiinin kidemuunnos, menetelmä sen valmistamiseksi ja käyttö
EP0096142B1 (fr)	1989-01-18	Sulfényl pyrrole microbicide
CA1262143A (fr)	1989-10-03	Derives de formylglycine
DD295160A5 (de)	1991-10-24	Mikrobizide mittel
US4546109A (en)	1985-10-08	Organotin compounds and pesticidal compositions
EP0132826A1 (fr)	1985-02-13	Dérivés de la N-(nitro-2 phényl)amino-5 pyrimidine, leur préparation et leur application
EP0462931B1 (fr)	1994-04-13	Dérivés de benzotriazole-1-sulfonyle à propriétés microbicides
CA1256884A (fr)	1989-07-04	Procede de production de 3-cyano-4-phenylpyrroles
EP0207000B1 (fr)	1989-11-08	Microbicides
CA1273943A (fr)	1990-09-11	3-trifluoromethyl-4-phenylpyrroles