DE2232730A1 - Substituierte cyclohexan-2,6-dion-1carbonsaeureanilide und -thioanilide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und fungizide - Google Patents
Substituierte cyclohexan-2,6-dion-1carbonsaeureanilide und -thioanilide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und fungizideInfo
- Publication number
- DE2232730A1 DE2232730A1 DE2232730A DE2232730A DE2232730A1 DE 2232730 A1 DE2232730 A1 DE 2232730A1 DE 2232730 A DE2232730 A DE 2232730A DE 2232730 A DE2232730 A DE 2232730A DE 2232730 A1 DE2232730 A1 DE 2232730A1
- Authority
- DE
- Germany
- Prior art keywords
- dione
- formula
- thioanilides
- halogen
- alkyl
- 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.)
- Pending
Links
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- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001177161 Stegobium paniceum Species 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241001065719 Tetranychus ludeni Species 0.000 description 1
- 241001617088 Thanatephorus sasakii Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241001238451 Tortrix viridana Species 0.000 description 1
- 241001414831 Triatoma infestans Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 241000267822 Trogoderma granarium Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 208000003152 Yellow Fever Diseases 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 235000015241 bacon Nutrition 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000021279 black bean Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000008429 bread Nutrition 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
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- TZJGKEPNZDAOES-UHFFFAOYSA-N ethyl 2-methyl-4,6-dioxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1C(C)CC(=O)CC1=O TZJGKEPNZDAOES-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
- 239000010985 leather Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000020044 madeira Nutrition 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2232730A DE2232730A1 (de) | 1972-07-04 | 1972-07-04 | Substituierte cyclohexan-2,6-dion-1carbonsaeureanilide und -thioanilide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und fungizide |
| LU67692A LU67692A1 (enrdf_load_stackoverflow) | 1972-07-04 | 1973-05-29 | |
| BR4833/73A BR7304833D0 (pt) | 1972-07-04 | 1973-06-29 | As mposicoes inseticidas, acaricidas e fungicidas a base destido ciclohexano-2,6-diono-1-carboxilico substituidas, e coprocesso para a preparacao de anilidas e tioanilidas de a |
| CH963873A CH568963A5 (enrdf_load_stackoverflow) | 1972-07-04 | 1973-07-02 | |
| AU57608/73A AU5760873A (en) | 1972-07-04 | 1973-07-02 | NOVEL CYCLOHEXANE-2, 6-DIONE-l-CARBOXYLIC ACID ANILIDES AND THIOANILIDES, A PROCESS FOR THEIR PREPARATION AND THEIR USE AS INSECTICIDES, ACARICIDES AND FUNGICIDES |
| NL7309198A NL7309198A (enrdf_load_stackoverflow) | 1972-07-04 | 1973-07-02 | |
| IL42638A IL42638A0 (en) | 1972-07-04 | 1973-07-02 | Cyclohexane-2,6-dione-1-carboxylic acid anilides and thioanilides,their preparation and their use as insecticides,acaricides and fungicides |
| IT26104/73A IT990867B (it) | 1972-07-04 | 1973-07-02 | Anilidi e tioanilidi cicloesan 2 6 dion i carbossiliche sostituite per la loro produzione e loro impiego come insetticidi acaricidi e fungicidi |
| GB3157773A GB1377319A (en) | 1972-07-04 | 1973-07-03 | Cyclohexane-2,6-dione-1-carboxylic acid anilides and thioanilides a process for their preparation and their use as insecticides acaricides and fungicides |
| BE133061A BE801842A (fr) | 1972-07-04 | 1973-07-03 | Nouveaux anilides et thioanilides substitues d'acide cyclohexane-2,6-dione-carboxylique |
| ZA734470A ZA734470B (en) | 1972-07-04 | 1973-07-03 | Novel cyclohexane-2,6-dione-1-carboxylic acid anilides and thioanilides,a process for their preparation and their use as insecticides,acaricides and fungicides |
| IE1104/73A IE37868B1 (en) | 1972-07-04 | 1973-07-03 | Novel cyclohexane-2,6-dione-1-carboxylic acid anilides and thioanilides a process for their preparation and their use as insecticides acaricides and fungicides |
| FR737324599A FR2190806B1 (enrdf_load_stackoverflow) | 1972-07-04 | 1973-07-04 | |
| JP48074948A JPS49100225A (enrdf_load_stackoverflow) | 1972-07-04 | 1973-07-04 | |
| JP48074947A JPS49100054A (enrdf_load_stackoverflow) | 1972-07-04 | 1973-07-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2232730A DE2232730A1 (de) | 1972-07-04 | 1972-07-04 | Substituierte cyclohexan-2,6-dion-1carbonsaeureanilide und -thioanilide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2232730A1 true DE2232730A1 (de) | 1974-01-24 |
Family
ID=5849630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2232730A Pending DE2232730A1 (de) | 1972-07-04 | 1972-07-04 | Substituierte cyclohexan-2,6-dion-1carbonsaeureanilide und -thioanilide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und fungizide |
Country Status (14)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2601780A1 (de) * | 1976-01-20 | 1977-07-21 | Bayer Ag | Substituierte n-phenyl-n'-benzoyl- harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| EP0126713A3 (en) * | 1983-05-18 | 1985-04-17 | Ciba-Geigy Ag | Cyclohexanedione-carboxylic-acid derivatives having a herbicidal and plant growth regulating activity |
| US4803268A (en) * | 1984-10-02 | 1989-02-07 | Ciba-Geigy Corporation | Process for the preparation of cyclohexanedionecarboxylic acid derivatives |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA843727B (en) * | 1983-05-18 | 1985-01-30 | Ciba Geigy Ag | Cyclohexanedionecarboxylic acid derivatives with herbicidal and plant growth regulating properties |
| WO2023127808A1 (ja) * | 2021-12-28 | 2023-07-06 | 株式会社Adeka | アリールシクロヘキサンジオン誘導体又はその塩類及び該化合物を含有する有害生物防除剤並びにその使用方法 |
| EP4458807A1 (en) * | 2021-12-28 | 2024-11-06 | Adeka Corporation | Aryl cyclohexanedione derivative or salt thereof, pest control agent containing same, and method for use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1327154A (en) * | 1971-01-15 | 1973-08-15 | American Cyanamid Co | Dioxocyclohexenecarboxanilide insecticides and acaricides |
-
1972
- 1972-07-04 DE DE2232730A patent/DE2232730A1/de active Pending
-
1973
- 1973-05-29 LU LU67692A patent/LU67692A1/xx unknown
- 1973-06-29 BR BR4833/73A patent/BR7304833D0/pt unknown
- 1973-07-02 IT IT26104/73A patent/IT990867B/it active
- 1973-07-02 IL IL42638A patent/IL42638A0/xx unknown
- 1973-07-02 NL NL7309198A patent/NL7309198A/xx unknown
- 1973-07-02 AU AU57608/73A patent/AU5760873A/en not_active Expired
- 1973-07-02 CH CH963873A patent/CH568963A5/xx not_active IP Right Cessation
- 1973-07-03 BE BE133061A patent/BE801842A/xx unknown
- 1973-07-03 ZA ZA734470A patent/ZA734470B/xx unknown
- 1973-07-03 GB GB3157773A patent/GB1377319A/en not_active Expired
- 1973-07-03 IE IE1104/73A patent/IE37868B1/xx unknown
- 1973-07-04 JP JP48074948A patent/JPS49100225A/ja active Pending
- 1973-07-04 JP JP48074947A patent/JPS49100054A/ja active Pending
- 1973-07-04 FR FR737324599A patent/FR2190806B1/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2601780A1 (de) * | 1976-01-20 | 1977-07-21 | Bayer Ag | Substituierte n-phenyl-n'-benzoyl- harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| EP0126713A3 (en) * | 1983-05-18 | 1985-04-17 | Ciba-Geigy Ag | Cyclohexanedione-carboxylic-acid derivatives having a herbicidal and plant growth regulating activity |
| US4693745A (en) * | 1983-05-18 | 1987-09-15 | Ciba-Geigy Corporation | Cyclohexanedionecarboxylic acid derivatives with herbicidal and plant growth regulating properties |
| US4803268A (en) * | 1984-10-02 | 1989-02-07 | Ciba-Geigy Corporation | Process for the preparation of cyclohexanedionecarboxylic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA734470B (en) | 1974-05-29 |
| CH568963A5 (enrdf_load_stackoverflow) | 1975-11-14 |
| FR2190806A1 (enrdf_load_stackoverflow) | 1974-02-01 |
| LU67692A1 (enrdf_load_stackoverflow) | 1973-08-02 |
| FR2190806B1 (enrdf_load_stackoverflow) | 1977-02-18 |
| GB1377319A (en) | 1974-12-11 |
| BE801842A (fr) | 1974-01-03 |
| IL42638A0 (en) | 1973-10-25 |
| IE37868B1 (en) | 1977-10-26 |
| AU5760873A (en) | 1975-01-09 |
| NL7309198A (enrdf_load_stackoverflow) | 1974-01-08 |
| BR7304833D0 (pt) | 1974-08-15 |
| JPS49100054A (enrdf_load_stackoverflow) | 1974-09-20 |
| JPS49100225A (enrdf_load_stackoverflow) | 1974-09-21 |
| IT990867B (it) | 1975-07-10 |
| IE37868L (en) | 1974-01-04 |
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