GB2093448A - Acylated hydrazine carboxylates - Google Patents
Acylated hydrazine carboxylates Download PDFInfo
- Publication number
- GB2093448A GB2093448A GB8202779A GB8202779A GB2093448A GB 2093448 A GB2093448 A GB 2093448A GB 8202779 A GB8202779 A GB 8202779A GB 8202779 A GB8202779 A GB 8202779A GB 2093448 A GB2093448 A GB 2093448A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- 4alkyl
- halogen
- ch2och3
- 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.)
- Withdrawn
Links
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical class NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 16
- 241000233866 Fungi Species 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000000417 fungicide Substances 0.000 claims abstract description 12
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- -1 2-tetrahydrofuryl Chemical group 0.000 claims description 14
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000002168 alkylating agent Substances 0.000 claims description 6
- 229940100198 alkylating agent Drugs 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 238000007126 N-alkylation reaction Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 241000233654 Oomycetes Species 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 241001223281 Peronospora Species 0.000 claims description 2
- 241000233614 Phytophthora Species 0.000 claims description 2
- 241000233626 Plasmopara Species 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 29
- JXRUECMXTRXHNY-UHFFFAOYSA-N methyl n-(n-(2-methoxyacetyl)-2,6-dimethylanilino)-n-methylcarbamate Chemical compound COCC(=O)N(N(C)C(=O)OC)C1=C(C)C=CC=C1C JXRUECMXTRXHNY-UHFFFAOYSA-N 0.000 abstract description 3
- 241000196324 Embryophyta Species 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 238000009472 formulation Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229960004132 diethyl ether Drugs 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 4
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- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- SKQUUKNCBWILCD-UHFFFAOYSA-J dicopper;chloride;trihydroxide Chemical compound [OH-].[OH-].[OH-].[Cl-].[Cu+2].[Cu+2] SKQUUKNCBWILCD-UHFFFAOYSA-J 0.000 description 3
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- 239000004563 wettable powder Substances 0.000 description 3
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 2
- 239000005745 Captan Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 239000005789 Folpet Substances 0.000 description 2
- 244000025221 Humulus lupulus Species 0.000 description 2
- 235000008694 Humulus lupulus Nutrition 0.000 description 2
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- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 239000005802 Mancozeb Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 240000003829 Sorghum propinquum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- XLJPNJQXNNWRBP-UHFFFAOYSA-L [Ca].[Cu+2].[O-]S([O-])(=O)=O Chemical compound [Ca].[Cu+2].[O-]S([O-])(=O)=O XLJPNJQXNNWRBP-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001351 alkyl iodides Chemical class 0.000 description 2
- 229940117949 captan Drugs 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 2
- 229940112669 cuprous oxide Drugs 0.000 description 2
- 230000001586 eradicative effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 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 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 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 2
- 229920005610 lignin Polymers 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- 229920000940 maneb Polymers 0.000 description 2
- ZGGUGLWGPMYYRV-UHFFFAOYSA-N methyl n-(2,6-dimethylanilino)carbamate Chemical compound COC(=O)NNC1=C(C)C=CC=C1C ZGGUGLWGPMYYRV-UHFFFAOYSA-N 0.000 description 2
- DRICDTBTBFPDQA-UHFFFAOYSA-N methyl n-(n-(2-methoxyacetyl)-2,6-dimethylanilino)carbamate Chemical compound COCC(=O)N(NC(=O)OC)C1=C(C)C=CC=C1C DRICDTBTBFPDQA-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
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- 235000013311 vegetables Nutrition 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- CCHJMGDYNLOYKM-UHFFFAOYSA-N (2,6-dimethylphenyl)hydrazine Chemical compound CC1=CC=CC(C)=C1NN CCHJMGDYNLOYKM-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000005739 Bordeaux mixture Substances 0.000 description 1
- 241000233684 Bremia Species 0.000 description 1
- 241000233685 Bremia lactucae Species 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000218631 Coniferophyta Species 0.000 description 1
- 239000004128 Copper(II) sulphate Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
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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 1
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- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- XAMVGJCPVGBYGO-UHFFFAOYSA-L [OH-].[OH-].[Cu+2].OCCN(CCO)CCO Chemical compound [OH-].[OH-].[Cu+2].OCCN(CCO)CCO XAMVGJCPVGBYGO-UHFFFAOYSA-L 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
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- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
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- ATSGLBOJGVTHHC-UHFFFAOYSA-N bis(ethane-1,2-diamine)copper(2+) Chemical compound [Cu+2].NCCN.NCCN ATSGLBOJGVTHHC-UHFFFAOYSA-N 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- FJYLWRRKCXWXSR-UHFFFAOYSA-N calcium copper chloro hypochlorite Chemical compound [Ca+2].[Cu+2].ClOCl FJYLWRRKCXWXSR-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
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- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
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- 239000000470 constituent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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Classifications
-
- 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8103510 | 1981-02-05 | ||
| GB8130891 | 1981-10-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2093448A true GB2093448A (en) | 1982-09-02 |
Family
ID=26278336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8202779A Withdrawn GB2093448A (en) | 1981-02-05 | 1982-02-01 | Acylated hydrazine carboxylates |
Country Status (11)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0183650A1 (de) * | 1984-11-27 | 1986-06-04 | Ciba-Geigy Ag | Phenylhydrazine, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung |
| EP0261755A3 (en) * | 1986-09-26 | 1989-06-28 | Rohm And Haas Company | Five-membered heterocyclic derivatives of n'-substituted-n,n'-diacylhydrazines |
| WO2001017355A1 (en) * | 1999-09-07 | 2001-03-15 | Uniroyal Chemical Company, Inc. | Method for controlling fungi using phenylhydrazine derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2223936A1 (de) * | 1972-05-17 | 1973-12-06 | Bayer Ag | Fungizide mittel |
| EP0030923A1 (de) * | 1979-12-18 | 1981-06-24 | Ciba-Geigy Ag | 3-(N-Acyl-phenylamino)-oxazolidin-2-one, Verfahren zu ihrer Herstellung sowie deren Verwendung als Mikrobizide oder in mikrobiziden Mitteln |
| DE3030026A1 (de) * | 1980-08-08 | 1981-03-26 | Sandoz-Patent-GmbH, 79539 Lörrach | Fungizide |
| IT1149844B (it) * | 1980-10-03 | 1986-12-10 | Montedison Spa | Carbazati fungicidi |
-
1982
- 1982-01-26 FR FR8201386A patent/FR2499074A1/fr active Granted
- 1982-01-27 DE DE19823202487 patent/DE3202487A1/de not_active Withdrawn
- 1982-02-01 NL NL8200353A patent/NL8200353A/nl not_active Application Discontinuation
- 1982-02-01 GB GB8202779A patent/GB2093448A/en not_active Withdrawn
- 1982-02-03 IT IT47716/82A patent/IT1189216B/it active
- 1982-02-03 IL IL64925A patent/IL64925A0/xx unknown
- 1982-02-03 AU AU80168/82A patent/AU8016882A/en not_active Abandoned
- 1982-02-04 DK DK48782A patent/DK48782A/da not_active Application Discontinuation
- 1982-02-04 PT PT74388A patent/PT74388A/pt unknown
- 1982-02-04 BR BR8200613A patent/BR8200613A/pt unknown
- 1982-02-04 PL PL23495782A patent/PL234957A1/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0183650A1 (de) * | 1984-11-27 | 1986-06-04 | Ciba-Geigy Ag | Phenylhydrazine, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung |
| US4725302A (en) * | 1984-11-27 | 1988-02-16 | Ciba-Geigy Corporation | Substituted phenylhydrazines and phenyloxadiazolinones and pesticidal usage thereof |
| EP0261755A3 (en) * | 1986-09-26 | 1989-06-28 | Rohm And Haas Company | Five-membered heterocyclic derivatives of n'-substituted-n,n'-diacylhydrazines |
| WO2001017355A1 (en) * | 1999-09-07 | 2001-03-15 | Uniroyal Chemical Company, Inc. | Method for controlling fungi using phenylhydrazine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| PT74388A (en) | 1982-03-01 |
| IT1189216B (it) | 1988-01-28 |
| DE3202487A1 (de) | 1982-09-02 |
| NL8200353A (nl) | 1982-09-01 |
| AU8016882A (en) | 1982-08-12 |
| FR2499074B1 (enrdf_load_stackoverflow) | 1984-11-09 |
| DK48782A (da) | 1982-08-06 |
| PL234957A1 (enrdf_load_stackoverflow) | 1982-10-11 |
| BR8200613A (pt) | 1982-12-14 |
| IL64925A0 (en) | 1982-04-30 |
| IT8247716A0 (it) | 1982-02-03 |
| FR2499074A1 (fr) | 1982-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |