IL26080A - Bicyclic sulphamides,their preparation and use as pest repellents - Google Patents
Bicyclic sulphamides,their preparation and use as pest repellentsInfo
- Publication number
- IL26080A IL26080A IL26080A IL2608066A IL26080A IL 26080 A IL26080 A IL 26080A IL 26080 A IL26080 A IL 26080A IL 2608066 A IL2608066 A IL 2608066A IL 26080 A IL26080 A IL 26080A
- Authority
- IL
- Israel
- Prior art keywords
- preparation
- reaction
- compound
- sulphamides
- carried out
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000002940 repellent Effects 0.000 title description 6
- 239000005871 repellent Substances 0.000 title description 6
- 241000607479 Yersinia pestis Species 0.000 title description 2
- 125000002619 bicyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 230000001846 repelling effect Effects 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 1
- 241000255925 Diptera Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 241000256118 Aedes aegypti Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 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
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical class NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000134316 Culicoides <genus> Species 0.000 description 1
- 241000268912 Damalinia Species 0.000 description 1
- 241001513837 Dermestes maculatus Species 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000519875 Exomala orientalis Species 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
- 241001660201 Gasterophilus intestinalis Species 0.000 description 1
- 241000257324 Glossina <genus> Species 0.000 description 1
- 241001608644 Hippoboscidae Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 241000256686 Lasius <genus> Species 0.000 description 1
- 241000131091 Lucanus cervus Species 0.000 description 1
- 241000257162 Lucilia <blowfly> Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000543819 Oestrus ovis Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241000517325 Pediculus Species 0.000 description 1
- 241000255129 Phlebotominae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000718000 Pulex irritans Species 0.000 description 1
- 241000722249 Rhodnius prolixus Species 0.000 description 1
- 241000257190 Sarcophaga <genus> Species 0.000 description 1
- 241000509416 Sarcoptes Species 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241001414833 Triatoma Species 0.000 description 1
- 241000429635 Xestobium rufovillosum Species 0.000 description 1
- RRUROMNUPPONFR-UHFFFAOYSA-L [Na+].[Na+].[O-]C([O-])=O.CCN(CC)CC Chemical compound [Na+].[Na+].[O-]C([O-])=O.CCN(CC)CC RRUROMNUPPONFR-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- KNONOKQJACDNOZ-UHFFFAOYSA-N n-ethylethanamine;propan-2-amine Chemical compound CC(C)N.CCNCC KNONOKQJACDNOZ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- -1 polyoxyethylene Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/04—Diamides of sulfuric acids
- C07C307/06—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to acyclic carbon atoms
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Bicyclio their preparation and as peet repellents 24855 in bicyelie of general wherein each or is hydrogen or is or Is it Θ or These compounds possess strong and properties are substantially stronger than those of knovm insect Where in the above or are alkyl these contain preferably carbon where is an it may contain carbon invention also provides processes for the preparation of the compounds of formula one of a amine of the general is reacted with a chloride of the general In which formulae and have the same meaning as By another process the nda of I can be prepared the reaction a bicyelic sulphamlc acid chloride of the with an amine of the l in which formulae and n the same meaninge as in formula Examples amines of the formula II which can be used as starting materials in the process of the invention de the and these are readily for from diene addition and some also from natural The aainee formula V are The following may sten way of diethylamide isopropylamine lamine hydroxylamine and The sulphamic acid chlorides of general formula used for the reaction with the amines of general formula are derived from the above amines of general formula and can be prepared from the latter in known for by reaction with s lphuryl The sulphamic acid chlorides of general formula are In the production of the compounds by one of the two it is advantageous to use such as aromatic ketones and and such as triethylamine sodium carbonate or sodium hydroxide The reaction temperatures used are preferably between 0 and The reactions are expediently carried out with approximately of the reaction in the resence of least the equivalent amount of an and in the simultaneous presence of a The agents may also be replaced by an excess of the corresponding amine Working up is carried out in conventional The new com ounds according to the present invention exhibit a strong action against besides a low toxicity a ainst The effect lasts a long They be with good for repelling obnoxious sucking and biting insects and The sucking insects essentially include such as the species Culex and Anopheles sand flies such as biting such as Culicoides buffalo such as the stinging such as the stable fly the tsetse flies horse such as the Haemotopota and Chr sops the housefly the lesser housefly the meat such as Sarcophaga flies causing such as Lucilia Hypoderma Hypoderma Oestrus ovis Gasterophilus intestinalis and Qochlimyia hominivorax such as Cimex lectularius Rhodnius prolixus and Triatoma such as Pediculus Haemotopinua suis and Damalinia keds such as such as the human flea and Ctenocephalus and sand such as The biting insects essentially include such as the German cockroach the oriental beetle such as the grain weevil the stag beetle the death watch beetle the leather beetle the mealworm beetle and such as and such as Lasius The mites include such as Ornithodoros Boop and in the stricter such gallinae and Sarcoptes The active compounds according to the present invention can be used either undiluted can be converted into the usual such as lacquers or These are prepared in known for by mixing the active compounds with liquid and solid diluents and optionally with the use emulsifying agents dispersion In the case of the use of water as an organic solvents for also be used as auxiliary As liquid diluents or there are preferably used aromatic such as xylenes or chlorinated aromatic nydrocarbons such as chlorobenzene such as mineral oil such as ethanol or animal end vegetable such as olive oil or nut and strongly polar such as dimethyl sulphoxide or dimethyl formamide as well as As solid diluents there are preferably used ground natural such talc or and ground synthetic such as silicic acid or Preferred examples of emulsifying agents include and anionic such as polyoxyethylene fatty alcohol for alkyl aryl polyglycol alkyl sulphonates and aryl preferred examples of dispersing agents include lignin e waste liquors and methyl The active compounds according to the present invention can be present in the formulations mixed with one another or also in admixture with known active The formulations generally contain between and preferably between and per cent by weight of the active For protection against insects or the active compounds according to the present invention are applied to the human or animal skin or clothes or other articles are impregnated with repelling pests damaging foodstuff or other substances to be protected are treated with the agents directly or they are applied to areas around the ma to be thus creating inhibition zones against the penetration of the The active compounds can be used as in the of their formulations or in the of made therefrom for They are applied in the usual manner by rubbing pouring or The concentrations of the active agents can be caried within a fairly large In the active compounds are used in concentrations of preferably Le A 9530 The preparation of some of the active compounds to be used according to the present invention is described in greater detail in the Example g dimethyl carbamic acid chloride are added o dropwise at 10 20 to a solution of l and 9 in methylene the reaction mixture is heated under reflux for 4 the reaction product poured into a concentrated potassium carbonate solution and the organic phase is After distillation of the organic there are obtained 21 material is obtained by monoinethylation of 2 in is formed by hydrogenation of the addition product of acrylonitrile with There obtained by similar A 9530 170 144 1 Example 28 are added dropwise at while stirring to the reaction mixture is heatea at overnight and then the reaction product is taken up in After distilling off the there remains a residue of which essentially consists of acid The latter is by the method described in Example with 8 in 100 methylene chloride in the presence of 10 triethylamine There are obtained 15 142 1 The following Examples are given to illustrate the utility of the new compounds according to the present inventio Example Repellent test mosquitoes test Aedes aegypti alcohol To produce a suitable preparation of the active 5 parts by weight of active compound are mixed with 100 parts by volume of the The hair is shaven off from the backs of guinea 2 pigs to an extent of cm of the preparation of the active compound are uniformly distributed over this shaven The animals are then placed in narrow cages of fine wire which leaves the shaven area of the In these wire the guinea pigs are placed for 10 minutes in larger in which several thousand hungry mosquitoes are flying It is observed whether the mosquitoes bite the guinea pigs on the treated The placing of the guinea pig cages into the larger cages is repeated every The repellent action is regarded as terminated when guinea pig is bitten by than one mosquito during the period of active test animals and duration of the repellent effect can be seen from tae following Le A Table mosquitoes Active compound animal Duration of repellent action in ours Aedes aegypti 8 insufficientOCRQuality
Claims (1)
1. of the general formulas wherein each E independently hydrogen or is hydrogen or alkyl or is 2 or and n 0 or compound of The of the The compound of the formula The compound of the The of the formula The compound of the of the anides of 1 in substantially described with reference to Examples A and A process for the of clic ides according to Claim of the is reacted h a chloride of in which the meaning Claim process for the preparation of according to Claim wherein a acifi chloride of the general is reacted an amine of the general in which formulae R and n the same meanings as in Claim A process according to Claim 11 or wherein the reaction is carried out in the presence of a A process according any of wherein the reaction is carried out in the presence of an binding A according of Claims wherein the reaction is carried out at a temperature between and Processes for the preparation substituted sulphamides according to Claim substantially as herein described and according to when prepared by a process according to any of Claims and epellent compositions as active a according to Claim in admixture a or liquid diluent or A repelling insec wherein there is applied to or around from which insects to he a bicyclie according admixture with a solid or diluent PARTNERS insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0046710 | 1965-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL26080A true IL26080A (en) | 1970-01-29 |
Family
ID=7101189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL26080A IL26080A (en) | 1965-07-24 | 1966-07-03 | Bicyclic sulphamides,their preparation and use as pest repellents |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3513182A (en) |
| BE (1) | BE684461A (en) |
| CH (1) | CH480010A (en) |
| DE (1) | DE1542785A1 (en) |
| ES (1) | ES329428A1 (en) |
| GB (1) | GB1111706A (en) |
| IL (1) | IL26080A (en) |
| NL (1) | NL6610372A (en) |
| SE (1) | SE335252B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY147767A (en) | 2004-06-16 | 2013-01-31 | Janssen Pharmaceutica Nv | Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders |
| MX2007014613A (en) | 2005-05-20 | 2008-04-02 | Johnson & Johnson | Process for preparation of sulfamide derivatives. |
| US8937096B2 (en) | 2005-12-19 | 2015-01-20 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocyle sulfamide derivatives for the treatment of mania and bipolar disorder |
| US8497298B2 (en) | 2005-12-19 | 2013-07-30 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for lowering lipids and lowering blood glucose levels |
| AR058389A1 (en) | 2005-12-19 | 2008-01-30 | Janssen Pharmaceutica Nv | USE OF SULFAMIDE BENZO-FUSED HETEROCICLIC DERIVATIVES FOR THE TREATMENT OF OBESITY |
| US8691867B2 (en) | 2005-12-19 | 2014-04-08 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of substance abuse and addiction |
| US8716231B2 (en) | 2005-12-19 | 2014-05-06 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of pain |
| WO2007137167A2 (en) | 2006-05-19 | 2007-11-29 | Janssen Pharmaceutica N.V. | Co-therapy for the treatment of epilepsy |
| AU2009271362B2 (en) | 2008-06-23 | 2014-03-13 | Janssen Pharmaceutica Nv | Crystalline form of (2s)-(-)-N-(6-chloro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-sulfamide |
| US8815939B2 (en) | 2008-07-22 | 2014-08-26 | Janssen Pharmaceutica Nv | Substituted sulfamide derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL89282C (en) * | 1954-05-14 | |||
| US2768971A (en) * | 1954-05-26 | 1956-10-30 | Ici Ltd | Preparation of alkyl-aryl-ureas |
| US3304167A (en) * | 1960-12-15 | 1967-02-14 | Hercules Inc | Norbornyl and substituted norbornyl ureas and thioureas, weed control compositions and methods |
| CH398543A (en) * | 1961-05-06 | 1966-03-15 | Ciba Geigy | Process for the production of urea derivatives |
-
1965
- 1965-07-24 DE DE19651542785 patent/DE1542785A1/en active Pending
-
1966
- 1966-07-01 CH CH955266A patent/CH480010A/en not_active IP Right Cessation
- 1966-07-03 IL IL26080A patent/IL26080A/en unknown
- 1966-07-18 US US565673A patent/US3513182A/en not_active Expired - Lifetime
- 1966-07-21 GB GB32767/66A patent/GB1111706A/en not_active Expired
- 1966-07-22 NL NL6610372A patent/NL6610372A/xx unknown
- 1966-07-22 SE SE10074/66A patent/SE335252B/xx unknown
- 1966-07-22 BE BE684461D patent/BE684461A/xx unknown
- 1966-07-23 ES ES0329428A patent/ES329428A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES329428A1 (en) | 1967-05-16 |
| SE335252B (en) | 1971-05-17 |
| NL6610372A (en) | 1967-01-25 |
| CH480010A (en) | 1969-10-31 |
| BE684461A (en) | 1967-01-23 |
| GB1111706A (en) | 1968-05-01 |
| DE1542785A1 (en) | 1970-05-06 |
| US3513182A (en) | 1970-05-19 |
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