IL42639A - 3 - Amino - 2, 4, 6 - Trichloro - benzaldehyde sulfonylhydrazones, processes for their production and preparations containing them for exterminating animals from rabbit ointment and rodents - Google Patents
3 - Amino - 2, 4, 6 - Trichloro - benzaldehyde sulfonylhydrazones, processes for their production and preparations containing them for exterminating animals from rabbit ointment and rodentsInfo
- Publication number
- IL42639A IL42639A IL42639A IL4263973A IL42639A IL 42639 A IL42639 A IL 42639A IL 42639 A IL42639 A IL 42639A IL 4263973 A IL4263973 A IL 4263973A IL 42639 A IL42639 A IL 42639A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- benzaldehyde
- trichloro
- combating
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 241001465754 Metazoa Species 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 title claims description 18
- 241000283984 Rodentia Species 0.000 title claims description 12
- IOUOJAQHWQONOY-UHFFFAOYSA-N 3-amino-2,4,6-trichlorobenzaldehyde Chemical compound NC=1C(=C(C=O)C(=CC1Cl)Cl)Cl IOUOJAQHWQONOY-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 52
- 239000003085 diluting agent Substances 0.000 claims description 16
- -1 alkyl radicals Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 241000607479 Yersinia pestis Species 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 241000700159 Rattus Species 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000002574 poison Substances 0.000 description 4
- 231100000614 poison Toxicity 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- UKEFCCZDGFXTDE-UHFFFAOYSA-N 2,4,6-trichloro-3-methanehydrazonoylaniline Chemical compound NC=1C(=C(C=NN)C(=CC1Cl)Cl)Cl UKEFCCZDGFXTDE-UHFFFAOYSA-N 0.000 description 2
- PIVQQUNOTICCSA-UHFFFAOYSA-N ANTU Chemical compound C1=CC=C2C(NC(=S)N)=CC=CC2=C1 PIVQQUNOTICCSA-UHFFFAOYSA-N 0.000 description 2
- 241000699677 Cricetus cricetus Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241001147360 Microtus agrestis Species 0.000 description 2
- 241000215542 Microtus arvalis Species 0.000 description 2
- 241000157049 Microtus richardsoni Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700161 Rattus rattus Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000006011 Zinc phosphide Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229940095076 benzaldehyde Drugs 0.000 description 2
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- HOKBIQDJCNTWST-UHFFFAOYSA-N phosphanylidenezinc;zinc Chemical compound [Zn].[Zn]=P.[Zn]=P HOKBIQDJCNTWST-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001119 rodenticidal effect Effects 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 229940048462 zinc phosphide Drugs 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SSULGNXFUGLULI-UHFFFAOYSA-N 4-chloro-3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SSULGNXFUGLULI-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241001529471 Arvicolinae Species 0.000 description 1
- 241001291468 Callospermophilus lateralis Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 241000131390 Glis Species 0.000 description 1
- 241000131388 Glis glis Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000283953 Lagomorpha Species 0.000 description 1
- 241000283960 Leporidae Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000699729 Muridae Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241000283925 Spermophilus Species 0.000 description 1
- 241000283920 Spermophilus citellus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000501807 Thomomys monticola Species 0.000 description 1
- 241001494940 Thomomys talpoides Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 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
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 230000004634 feeding behavior Effects 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011868 grain product Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 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
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 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
- 238000010992 reflux Methods 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2306918A DE2306918A1 (de) | 1973-02-13 | 1973-02-13 | Benzaldehyd-sulfonylhydrazone, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von hasenartigen und nagetieren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42639A0 IL42639A0 (en) | 1973-10-25 |
| IL42639A true IL42639A (en) | 1976-03-31 |
Family
ID=5871705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42639A IL42639A (en) | 1973-02-13 | 1973-07-02 | 3 - Amino - 2, 4, 6 - Trichloro - benzaldehyde sulfonylhydrazones, processes for their production and preparations containing them for exterminating animals from rabbit ointment and rodents |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3912779A (da) |
| JP (3) | JPS573673B2 (da) |
| BE (1) | BE801843A (da) |
| BR (1) | BR7304961D0 (da) |
| CA (1) | CA983955A (da) |
| CH (1) | CH584508A5 (da) |
| DE (1) | DE2306918A1 (da) |
| DK (1) | DK135840C (da) |
| FR (1) | FR2236851B1 (da) |
| GB (1) | GB1374407A (da) |
| HK (1) | HK47277A (da) |
| IE (1) | IE37864B1 (da) |
| IL (1) | IL42639A (da) |
| IT (1) | IT994924B (da) |
| KE (1) | KE2767A (da) |
| LU (1) | LU67911A1 (da) |
| MY (1) | MY7800038A (da) |
| NL (1) | NL7309201A (da) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140795A (en) * | 1976-12-09 | 1979-02-20 | Ciba-Geigy Corporation | Pesticidal 1,3,5-triazapenta-1,4-dienes |
| GB2058057A (en) * | 1979-08-31 | 1981-04-08 | Boots Co Ltd | Pesticidal substituted benzophenone hydrazones |
| JPS58220266A (ja) * | 1982-06-16 | 1983-12-21 | Victor Co Of Japan Ltd | テ−プ自動装填装置 |
| DE3322320A1 (de) * | 1983-06-21 | 1985-01-03 | Bayer Ag, 5090 Leverkusen | Arylsulfonylhydrazone als treibmittel |
| US5198566A (en) * | 1989-02-08 | 1993-03-30 | Kureha Kagaku Kogyo K.K. | N-substituted-3-(substituted hydrazino)-benzenesulfonamides |
| CN102993045B (zh) * | 2012-12-02 | 2015-04-15 | 桂林理工大学 | 3,5-二溴水杨醛缩水合肼双希夫碱的原位合成方法 |
| CN103086919A (zh) * | 2013-01-24 | 2013-05-08 | 桂林理工大学 | 4-(二乙氨基)-水杨醛缩水合肼双希夫碱的原位合成方法 |
| CN103254098A (zh) * | 2013-05-31 | 2013-08-21 | 桂林理工大学 | 3,5-二氯水杨醛缩水合肼双希夫碱的原位合成方法 |
| WO2017125087A1 (zh) * | 2016-01-22 | 2017-07-27 | 大鹏药品工业株式会社 | 一种高纯度环己烯酮长链醇的制备方法 |
| CN110627692B (zh) * | 2019-10-14 | 2021-09-24 | 河南科技大学 | 丹皮酚苯磺酰腙及其衍生物和其制备方法、植物源杀虫剂及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709936A (en) * | 1970-11-16 | 1973-01-09 | Minnesota Mining & Mfg | Plant growth regulators |
-
1973
- 1973-02-13 DE DE2306918A patent/DE2306918A1/de not_active Withdrawn
- 1973-06-27 US US374195A patent/US3912779A/en not_active Expired - Lifetime
- 1973-06-29 CA CA175,328A patent/CA983955A/en not_active Expired
- 1973-07-02 LU LU67911A patent/LU67911A1/xx unknown
- 1973-07-02 NL NL7309201A patent/NL7309201A/xx not_active Application Discontinuation
- 1973-07-02 IE IE1097/73A patent/IE37864B1/xx unknown
- 1973-07-02 IL IL42639A patent/IL42639A/en unknown
- 1973-07-02 DK DK366273A patent/DK135840C/da not_active IP Right Cessation
- 1973-07-02 CH CH963973A patent/CH584508A5/xx not_active IP Right Cessation
- 1973-07-02 FR FR7324216A patent/FR2236851B1/fr not_active Expired
- 1973-07-02 GB GB3142273A patent/GB1374407A/en not_active Expired
- 1973-07-03 BE BE133062A patent/BE801843A/xx not_active IP Right Cessation
- 1973-07-03 JP JP7450973A patent/JPS573673B2/ja not_active Expired
- 1973-07-03 JP JP7451073A patent/JPS5635163B2/ja not_active Expired
- 1973-07-04 BR BR4961/73A patent/BR7304961D0/pt unknown
- 1973-07-06 IT IT26332/73A patent/IT994924B/it active
-
1977
- 1977-09-01 KE KE2767A patent/KE2767A/xx unknown
- 1977-09-15 HK HK472/77A patent/HK47277A/xx unknown
-
1978
- 1978-12-30 MY MY38/78A patent/MY7800038A/xx unknown
-
1981
- 1981-05-08 JP JP6845181A patent/JPS56166168A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DK135840C (da) | 1977-11-28 |
| CA983955A (en) | 1976-02-17 |
| JPS49110835A (da) | 1974-10-22 |
| DE2306918A1 (de) | 1974-08-15 |
| BE801843A (fr) | 1974-01-03 |
| JPS56166168A (en) | 1981-12-21 |
| IT994924B (it) | 1975-10-20 |
| IL42639A0 (en) | 1973-10-25 |
| HK47277A (en) | 1977-09-23 |
| DK135840B (da) | 1977-07-04 |
| FR2236851A1 (da) | 1975-02-07 |
| NL7309201A (da) | 1974-08-15 |
| IE37864B1 (en) | 1977-10-26 |
| MY7800038A (en) | 1978-12-31 |
| JPS5635163B2 (da) | 1981-08-15 |
| JPS5747186B2 (da) | 1982-10-07 |
| US3912779A (en) | 1975-10-14 |
| KE2767A (en) | 1977-10-21 |
| JPS573673B2 (da) | 1982-01-22 |
| GB1374407A (en) | 1974-11-20 |
| CH584508A5 (da) | 1977-02-15 |
| LU67911A1 (da) | 1973-09-05 |
| IE37864L (en) | 1974-08-13 |
| FR2236851B1 (da) | 1977-02-18 |
| BR7304961D0 (pt) | 1974-09-24 |
| JPS49102641A (da) | 1974-09-27 |
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