HU189269B - Pesticide compositions containing benzoyl-phenyl-car-bamide derivatives and process for preparing the active substances - Google Patents
Pesticide compositions containing benzoyl-phenyl-car-bamide derivatives and process for preparing the active substances Download PDFInfo
- Publication number
- HU189269B HU189269B HU831393A HU139383A HU189269B HU 189269 B HU189269 B HU 189269B HU 831393 A HU831393 A HU 831393A HU 139383 A HU139383 A HU 139383A HU 189269 B HU189269 B HU 189269B
- Authority
- HU
- Hungary
- Prior art keywords
- phenyl
- halogen
- song
- bowl
- formula
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000013543 active substance Substances 0.000 title 1
- 239000000575 pesticide Substances 0.000 title 1
- 239000004480 active ingredient Substances 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
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- 239000007787 solid Substances 0.000 claims description 9
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- 238000000034 method Methods 0.000 claims description 7
- XYFMGGWVGACNEC-UHFFFAOYSA-N n-carbamoyl-n-phenylbenzamide Chemical class C=1C=CC=CC=1N(C(=O)N)C(=O)C1=CC=CC=C1 XYFMGGWVGACNEC-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 5
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
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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 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 3
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
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- 150000001875 compounds Chemical class 0.000 abstract description 41
- 230000000361 pesticidal effect Effects 0.000 abstract description 7
- 125000001424 substituent group Chemical group 0.000 abstract description 5
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- 229910052731 fluorine Inorganic materials 0.000 description 14
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- 239000011737 fluorine Substances 0.000 description 13
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- 125000001246 bromo group Chemical group Br* 0.000 description 4
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- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 3
- ZRJSABISRHPRSB-UHFFFAOYSA-N 2,6-difluorobenzoyl isocyanate Chemical compound FC1=CC=CC(F)=C1C(=O)N=C=O ZRJSABISRHPRSB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 2-chlorobenzoyl isocyanate Chemical compound ClC1=CC=CC=C1C(=O)N=C=O ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 0.000 description 3
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- 241000256248 Spodoptera Species 0.000 description 3
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- 238000009835 boiling Methods 0.000 description 3
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- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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- DBXAHDCHRWVDEQ-UHFFFAOYSA-N n-(2-methylphenyl)sulfanyl-4-(trifluoromethoxy)aniline Chemical compound CC1=CC=CC=C1SNC1=CC=C(OC(F)(F)F)C=C1 DBXAHDCHRWVDEQ-UHFFFAOYSA-N 0.000 description 1
- PBUXSIXTCDTIQP-UHFFFAOYSA-N n-(2-nitrophenyl)sulfanyl-4-(trifluoromethoxy)aniline Chemical compound [O-][N+](=O)C1=CC=CC=C1SNC1=CC=C(OC(F)(F)F)C=C1 PBUXSIXTCDTIQP-UHFFFAOYSA-N 0.000 description 1
- JXAMZKLGWNOGSK-UHFFFAOYSA-N n-[[4-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl JXAMZKLGWNOGSK-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002728 pyrethroid Chemical class 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/18—Sulfenamides
- C07C313/26—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C313/30—Y being a hetero atom
- C07C313/34—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfenylureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/02—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of urea, its salts, complexes or addition compounds
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >NâCOâN< or >NâCSâN<
- A01N47/34—Ureas or thioureas containing the groups >NâCOâN< or >NâCSâN< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
A talĂĄlmĂĄny tĂĄrgya eljĂĄrĂĄs az Ășj (I) ĂĄltalĂĄnos kĂ©pletƱ benzoil-fenil-karbamid-szĂĄrmazĂ©kok elĆĂĄllĂtĂĄsĂĄra. A talĂĄlmĂĄny tĂĄrgyĂĄhoz tartoznak tovĂĄbbĂĄ az e vegyĂŒleteket hatĂłanyagkĂ©nt tartalmazĂł peszticid kĂ©szĂtmĂ©nyek is.
Ismeretes a szakirodalombĂłl (Chemie dĂ©r Pflanzenschutz und SchadlingsbekĂĄmpfungsmittel, 6. kötet, 423-470. oldal, 1981), hogy a benzoil-fenilkarbamid szĂĄrmazĂ©kok az inszekticidek 1970 körĂŒl felfedezett csoportjĂĄt alkotjĂĄk, Ă©s hatĂĄsmĂłdjuk kĂŒlönleges: ha a rovarlĂĄrvĂĄk inszekticiddel kezelt levelet vagy növĂ©nyt fogyasztanak, akkor olyan sĂșlyosan kĂĄrosodik a rovar vedlĂ©sĂ©nek termĂ©szetes folyamata, hogy ez a rovar pusztulĂĄsĂĄt okozza. E csoport vegyĂŒletei jellegzetesen magas olvadĂĄspontĂș szilĂĄrd anyagok, melyek csak kevĂ©ssĂ© oldĂłdnak vĂzben Ă©s a formĂĄlĂĄshoz hasznĂĄlt oldĂłszerekben. Ăgy talĂĄltĂĄk, hogy a kĂ©szĂtmĂ©nyek rĂ©szecskeĂĄtmĂ©rĆjĂ©nek lĂ©nyeges befolyĂĄsa van a biolĂłgiai hatĂ©konysĂĄgra, Ă©s a hatĂĄsossĂĄg növekszik a rĂ©szecskeĂĄtmĂ©rĆ csökkenĂ©sĂ©vel. Ennek megfelelĆen arra törekedtek, hogy olyan formĂĄlĂĄsi alakot dolgozzanak ki, amelynek segĂtsĂ©gĂ©vel a legfinomabb rĂ©szecskĂ©kbĆl ĂĄllĂł bevonat kĂ©pezhetĆ a levĂ©len vagy a növĂ©nyen. NyilvĂĄnvalĂł, hogy a legfinomabb bevonat oldatbĂłl keletkezhet, Ăgy pĂ©ldĂĄul a benzoilfenil-karbamid szĂĄrmazĂ©k emulgeĂĄlhatĂł koncentrĂĄtumĂĄbĂłl; ez azonban mindeddig nehĂ©zsĂ©gekbe ĂŒtközött e vegyĂŒletek nehezen kezelhetĆ jellege következtĂ©ben. JĂłllehet egyes benzoil-fenil-karbamid vegyĂŒletek oldhatĂłk bizonyos szerves oldĂłszerekben, de a hatĂłanyag vĂzben olyan rosszul oldĂłdik, hogy a kĂ©szĂtmĂ©ny hĂgĂtĂĄsakor a hatĂłanyag kicsapĂłdik, Ă©s Ăgy - az egyĂ©bkĂ©nt oldatban lĂ©vĆ - hatĂłanyag hatĂĄsa nem Ă©rvĂ©nyesĂŒl.
A talĂĄlmĂĄny szerinti benzoil-fenil-karbamidok inszekticid hatĂĄsa nagysĂĄgrendben megegyezik az ismert benzoil-fenil-karbamid szĂĄrmazĂ©kok hatĂ©konysĂĄgĂĄval, de a formĂĄlĂĄshoz hasznĂĄlt szerves oldĂłszerekben jobban oldĂłdnak, Ă©ĂĄ kevĂ©sbĂ© hajlamosak kicsapĂłdĂĄsra a vĂzzel valĂł hĂgĂtĂĄs sorĂĄn.
Az (I) åltalånos képletben
Hal jelentése halogénatom,
B jelentése hidrogén- vagy halogénatom,
X jelentĂ©se halogĂ©natom, trifluor-metil-, trifluormetoxi-csoport, tovĂĄbbĂĄ nitro- vagy ciano-, trifluor-metil-csoporttal vagy halogĂ©natommal egyszeresen vagy kĂ©tszeresen helyettesĂtett fenoxicsoport, n Ă©rtĂ©ke 1, 2 vagy 3,
R jelentĂ©se 1^4 szĂ©natomos halogĂ©n-alkilcsoport vagy adott esetben egy vagy kĂ©t nitrocsoporttal vagy 1-6 szĂ©natomos alkilcsoporttal vagy halogĂ©natommal egyszeresen helyettesĂtett fenilcsoport.
A Hal vagy B jelentĂ©sĂ©ben szereplĆ halogĂ©n lehet fluor-, klĂłr- vagy brĂłmatom, elĆnyös jelentĂ©se klĂłr- vagy fluoratom.
Az (I) ĂĄltalĂĄnos kĂ©pletƱ vegyĂŒletekben az X szubsztituens, vagy az X szubsztituensek egyike elĆnyösen az anilin csoportban a gyƱrƱ 4-helyzetĂ©ben van; ez a szerkezet a molekula hatĂĄsossĂĄgĂĄt fokozza.
Az X jelentĂ©sĂ©ben foglalt halogĂ©nezett alkil- vagy halogĂ©nezett alkoxicsoportok elĆnyösen 1-6 szĂ©natomot Ă©s 1-3 halogĂ©natomot, pĂ©ldĂĄul fluort, klĂłrt vagy brĂłmot tartalmaznak. E csoportok jelentĂ©se elĆnyösen trifluor-metil- Ă©s trifluor-metoxi-csoport.
Az X jelentĂ©sĂ©ben szereplĆ fenoxicsoport elĆnyös jelentĂ©se nitro-fenoxi-, (halogĂ©nezett alkil)fenoxi-, (halogĂ©nezett alkoxij-fenoxi- vagy (halogĂ©nezett alkil)-halogĂ©nezett-fenoxi-csoport, ahol a halogĂ©natomok fluor-, klĂłr- vagy brĂłmatomok, az alkil- Ă©s alkoxicsoportok pedig 1-4 szĂ©natomosak. Ezek közĂŒl pĂ©ldakĂ©nt emlĂtjĂŒk meg a 2-klĂłr-4-(trifluor-metil)-fenoxi- Ă©s a 4-nitro-fenoxi-csoportokat.
Az R csoport elĆnyös jelentĂ©se 1-4 szĂ©natomos halogĂ©nezett alkilcsoport, amely 1-3 fluor-, klĂłrvagy brĂłmatomot tartalmaz, tovĂĄbbĂĄ - adott esetben - egy vagy több (cĂ©lszerƱen egy vagy kĂ©t) nitro-, 1-6 szĂ©natomos alkilcsoporttal, vagy fluor-, klĂłr- vagy brĂłmatommal helyettesĂtett fenilcsoport. A talĂĄlmĂĄny szerinti vegyĂŒletek közĂŒl kĂŒlönösen hasznosak azok a szĂĄrmazĂ©kok, amelyekben R jelentĂ©se legalĂĄbb egy, elĆnyösen 2-helyzetben kötĆdĆ nitrocsoportot hordozĂł fenilcsoport.
A talĂĄlmĂĄny szerint az (I) ĂĄltalĂĄnos kĂ©pletƱ vegyĂŒletek közĂŒl elĆnyösek azok a szĂĄrmazĂ©kok, amelyek kĂ©pletĂ©ben
Hal jelentése fluor-, klór- vagy brómatom;
B jelentése hidrogén-, fluor-, klór- vagy brómatom;
X jelentĂ©se fluor-, klĂłr-, brĂłmatom, 1-4 szĂ©natomot Ă©s 1-3 fluor-, klĂłr- vagy brĂłmatomot tartalmazĂł metil- vagy halogĂ©nezett metoxiesoport, tovĂĄbbĂĄ nitro-fenoxi-, (halogĂ©nezett metil)-fenoxicsoport, ahol a halogĂ©natomkĂ©nt elĆnyösen fluoratom szerepel, n Ă©rtĂ©ke 1, 2 vagy 3; Ă©s
R jelentĂ©se 1â4 szĂ©natomot Ă©s cĂ©lszerƱen 1-3 fluoratomot tartalmazĂł alkilcsoport vagy - adott esetben - egy vagy kĂ©t nitro-, Ă©s 1-4 szĂ©natomos alkilcsoporttal, fluor-, klĂłr vagy brĂłmatommal helyettesĂtett fenilcsoport.
A kedvezĆ formĂĄlĂĄsi sajĂĄtsĂĄgok Ă©s az inszekticid hatĂĄs szempontjĂĄbĂłl az (I) ĂĄltalĂĄnos kĂ©pletƱ vegyĂŒletek közĂŒl legelĆnyösebbek azok, amelyek kĂ©pletĂ©ben
Hal jelentése fluor- vagy klóratom;
B jelentése hidrogén-, fluor- vagy klóratom;
X jelentése klóratom, trifluor-metoxi-, trifluormetil-, 2-klór-4-(trifluor-metil)-fenoxi- vagy 4-nitro-fenoxi-csoport, ahol X vagy az X szubsztituensek egyike a fenilcsoport gyƱrƱjének 4-helyzetében van;
n értéke 1, 2 vagy 3; és
R 2-nitro-fenil- vagy 2,4-dinitro-fenil-csoportot jelent.
Az (I) ĂĄltalĂĄnos kĂ©pletƱ vegyĂŒleteket a talĂĄlmĂĄny szerinti eljĂĄrĂĄssal Ășgy ĂĄllĂtjuk elĆ, hogy egy (II) ĂĄltalĂĄnos kĂ©pletƱ benzoil-izocianĂĄtot - a kĂ©pletben B Ă©s Hal jelentĂ©se az (I) ĂĄltalĂĄnos kĂ©pletben megadottal azonos - egy (III) ĂĄltalĂĄnos kĂ©pletƱ szulfenamiddal - a kĂ©pletben X, n Ă©s R jelentĂ©se az (I) kĂ©pletnĂ©l megadottal azonos - reagĂĄltatunk.
A reakciĂłt elĆnyösen protonmentes oldĂłszerben hajtjuk vĂ©gre. Alkalmazhatunk aromĂĄs oldĂłszereket, pĂ©ldĂĄul benzolt, toluolt, xilolt Ă©s klĂłr-benzolt; szĂ©nhidrogĂ©neket, Ăgy pĂ©ldĂĄul petrolĂ©tert (forrĂĄspontja 40-60 âC); klĂłrozott szĂ©nhidrogĂ©neket, pĂ©l-21
189 269 dåul kloroformot, diklór-metånt és diklór-etånt; étereket, példåul dietil-étert, dibutil-étert és a dioxånt.
CĂ©lszerƱ a reakciĂłt 0-100 °C hĆmĂ©rsĂ©klettartomĂĄnyban, elĆnyös 10-50°C közötti hĆmĂ©rsĂ©kleten vĂ©gezni. Az izocianĂĄtot az aminhoz viszonyĂtva elĆnyösen 1 : 1-2 : 1 mĂłlarĂĄnyban alkalmazzuk. Az Ăgy kapott tennĂ©k a szokĂĄsos mĂłdszerekkel dolgozhatĂł fel.
A (II) Ă©s (III) kĂ©pletƱ kiindulĂłanyagok isipert vegyĂŒletek, Ă©s ismert mĂłdszerekkel ĂĄllĂthatĂłk elĆ.
A talĂĄlmĂĄny szerinti vegyĂŒletek erĆs peszticid, Ăgy pĂ©ldĂĄul inszekticid hatĂĄst mutatnak. A talĂĄlmĂĄny tĂĄrgyĂĄhoz tartoznak azok a peszticid, elĆnyösen inszekticid kĂ©szĂtmĂ©nyek, melyek hatĂłanyagkĂ©nt egy talĂĄlmĂĄny szerinti (I) kĂ©pletƱ vegyĂŒletet tartalmaznak. A kĂ©szĂtmĂ©ny tartalmazhat egy vagy több talĂĄlmĂĄny szerinti vegyĂŒletet.
A talĂĄlmĂĄny szerinti kĂ©szĂtmĂ©nyek egy vagy több vivĆanyagot tartalmaznak. VivĆanyag lehet bĂĄrmely olyan anyag, amelynek segĂtsĂ©gĂ©vel a hatĂłanyag formĂĄlhatĂł, illetĆleg a kezelni kĂvĂĄnt helyre valĂł kijuttatĂĄst, vagy a tĂĄrolĂĄst, szĂĄllĂtĂĄst vagy a kezelĂ©st megkönnyĂti. A vivĆanyag lehet szilĂĄrd vagy cseppfolyĂłs; vagy olyan anyag is, amely normĂĄl ĂĄllapotĂĄban gĂĄz, azonban folyadĂ©kkĂĄ komprimĂĄlhatĂł. BĂĄrmely olyan vivĆanyag alkalmazhatĂł, amelyet a peszticid kĂ©szĂtmĂ©nyek formĂĄlĂĄsĂĄhoz ĂĄltalĂĄban alkalmaznak.
Alkalmas szilĂĄrd vivĆanyagok a termĂ©szetes Ă©s szintetikus agyagfĂ©lĂ©k Ă©s szilikĂĄtok, pĂ©ldĂĄul a termĂ©szetes kovasavfĂ©lĂ©k, amilyenek a diatomaföldek; a magnĂ©zium-szilikĂĄtok, pĂ©ldĂĄul a talkumfĂ©lĂ©k; a magnĂ©zium-alumĂnium-szilikĂĄtok, pĂ©ldĂĄul az attapulgit Ă©s vermikulit; az aluminium-szilikĂĄtok, pĂ©ldĂĄul a kaolinitok, montmorillonit Ă©s a csillĂĄmfĂ©lĂ©k; a kalcium-karbonĂĄt Ă©s kalcium-szulfĂĄt; a szintetikus, hidratĂĄlt szilĂcium-dioxidok, tovĂĄbbĂĄ a szintetikus kalcium- Ă©s aluminium-szilikĂĄtok; elemek, pĂ©ldĂĄul a szĂ©n Ă©s kĂ©n; termĂ©szetes Ă©s mƱgyantĂĄk, pĂ©ldĂĄul a kumarongyantĂĄk, poli(vinil-klorid), a sztirol polimerjei Ă©s kopolimerjei; a szilĂĄrd poli (klĂłr-fenol)-ok; a bitumen; a viaszfĂ©lĂ©k, pĂ©ldĂĄul a mĂ©hviasz, parafinviasz, Ă©s a klĂłrozott ĂĄsvĂĄnyi viaszok ; tovĂĄbbĂĄ a szilĂĄrd mƱtrĂĄgyafĂ©lĂ©k, Ăgy pĂ©ldĂĄul szuperfoszfĂĄtok.
Alkalmas cseppfolyĂłs vivĆanyagok: a vĂz; ketonok, pĂ©ldĂĄul az aceton, metil-etil-keton, metilizobutil-keton Ă©s cikiohexanon; Ă©terek; aromĂĄs vagy aril-alifĂĄs szĂ©nhidrogĂ©nek, pĂ©ldĂĄul a benzol, toluol Ă©s xilol; ĂĄsvĂĄnyolajfrakciĂłk, pĂ©ldĂĄul a kerozin Ă©s a könnyƱ ĂĄsvĂĄnyolajok; klĂłrozott szĂ©nhidrogĂ©nek, pĂ©ldĂĄul a szĂ©n-tetraklorid, perklĂłr-etilĂ©n Ă©s triklĂłr-etĂĄn. Gyakran hasznĂĄlhatĂłk kĂŒlönbözĆ folyadĂ©kok keverĂ©kei is.
A mezĆgazdasĂĄgban alkalmazott kĂ©szĂtmĂ©nyeket gyakran formĂĄljĂĄk Ă©s szĂĄllĂtjĂĄk tömĂ©ny formĂĄban, amelyet azutĂĄn a felhasznĂĄlĂł hĂgĂt fel a permetezĂ©s elĆtt. A hĂgĂtĂĄsi folyamatot megkönnyĂti kis mennyisĂ©gƱ felĂŒletaktĂv anyag jelenlĂ©te.
A felĂŒletaktĂv anyagkĂ©nt szerepelhet emulgeĂĄlĂłszer, diszpergĂĄlĂłszer vagy nedvesĂtĆszer, amely lehet ionos vagy nem-ionos jellegƱ. Az alkalmazhatĂł felĂŒletaktĂv szerekre pĂ©ldakĂ©nt szolgĂĄlnak a poliakrilsavak Ă©s ligninszulfonsavak kalcium- vagy nĂĄtriumsĂłi; a legalĂĄbb 12 szĂ©natomos zsĂrsavak vagy alifĂĄs aminok vagy savamidok etilĂ©n-oxiddal Ă©s/ vagy propilĂ©n-oxiddal alkotott kondenzĂĄciĂłs termĂ©kei; a glicerin, szorbitĂĄn, rĂ©pacukor vagy pentaeritrit zsĂrsavĂ©szterei; ez utĂłbbiak etilĂ©n-oxiddal Ă©s/vagy propilĂ©n-oxiddal alkotott kondenzĂĄtumai; zsĂralkoholok vagy alkil-fenolok - pĂ©ldĂĄul 4-oktilfenol, vagy 4-oktil-krezol - kondenzĂĄciĂłs termĂ©kei etilĂ©n-oxiddal Ă©s/vagy propilĂ©n-oxiddal; e kondenzĂĄciĂłs termĂ©kek szulfĂĄtjai vagy szulfonĂĄtjai; legalĂĄbb 10 szĂ©natomos kĂ©nsav- vagy szulfonsavĂ©szterek alkĂĄli- vagy alkĂĄliföldfĂ©msĂłi, elĆnyösen a nĂĄtriumsĂłi, Ăgy pĂ©ldĂĄul a nĂĄtrium-lauril-szulfĂĄt, nĂĄtrium-(szekunder-alkil)-szulfĂĄtok, a szulfonĂĄlt ricinusolaj nĂĄtriumsĂłi, tovĂĄbbĂĄ nĂĄtrium-(alkilaril)-szulfonĂĄtok, pĂ©ldĂĄul a nĂĄtrium-(dodecilbenzol)-szulfonĂĄt; tovĂĄbbĂĄ az etilĂ©n-oxid polimerjei Ă©s az etilĂ©n-oxidnak propilĂ©n-oxiddal alkotott kopolimerjei.
A talĂĄlmĂĄny szerinti kĂ©szĂtmĂ©nyek formĂĄlhatĂłk pĂ©ldĂĄul nedvesedĆ porok, permetporok, granulĂĄtumok, oldatok, emulgeĂĄlhatĂł koncentrĂĄtumok, emulziĂłk, szuszpendĂĄlhatĂł koncentrĂĄtumok Ă©s aeroszolok formĂĄjĂĄban. A nedvesedĆ porok ĂĄltalĂĄban 25, 50 Ă©s 75 sĂșly% hatĂłanyagot, tovĂĄbbĂĄ - a szilĂĄrd, közömbös vivĆanyagon kĂvĂŒl - ĂĄltalĂĄban
3-10 sĂșly % diszpergĂĄlĂłszert Ă©s szĂŒksĂ©ges esetben 0-10 sĂșly% stabilizĂĄlĂłszert (stabilizĂĄlĂłszereket), Ă©s/ vagy tovĂĄbbi adalĂ©kokat, Ăgy pĂ©ldĂĄul a hatĂłanyag behatolĂĄsĂĄt vagy megtapadĂĄsĂĄt könnyĂtĆ szereket tartalmaznak. A szĂłrĂłporokat ĂĄltalĂĄban koncentrĂĄtumok formĂĄjĂĄban formĂĄljuk, melyek összetĂ©tele hasonlĂł a nedvesedĆ por összetĂ©telĂ©hez, azonban nem tartalmaznak diszpergĂĄlĂłszert, Ă©s a szabadföldön hĂgĂtjuk tovĂĄbbi szilĂĄrd vivĆanyaggal Ășgy hogy 0,5-10 sĂșly% hatĂłanyagot tartalmazĂł kĂ©szĂtmĂ©nyhez jussunk. A granulĂĄtumot ĂĄltalĂĄban Ășgy kĂ©szĂtjĂŒk, hogy a rĂ©szecskĂ©k mĂ©rete 1,676-0,152 mm legyen, ezek kĂ©szĂthetĆk agglomerĂĄciĂłs vagy impregnĂĄlĂł eljĂĄrĂĄssal. A granulumok ĂĄltalĂĄban 0,5-25 sĂșly% aktĂv anyagot, tovĂĄbbĂĄ 0-10sĂșly% adalĂ©kanyagot, pĂ©ldĂĄul stabilizĂĄlĂłszereket, a hatĂłanyag lassĂș felszabadulĂĄsĂĄt szabĂĄlyozĂł anyagokat Ă©s kötĆanyagokat tĂĄrtain aznak. Az emulgeĂĄlhatĂł koncentrĂĄtumok az oldĂłszeren Ă©s - szĂŒksĂ©g esetĂ©n - a tĂĄrsoldĂłszeren kĂvĂŒl ĂĄltalĂĄban 10-50 sĂșly/tĂ©rfogat% hatĂłanyagot, 2-20 sĂșly/tĂ©rfogat% emulgeĂĄlĂłszert Ă©s 0-20 sĂșly/tĂ©rfogat% egyĂ©b adalĂ©kanyagot, pĂ©ldĂĄul stabilizĂĄlĂłszereket, a hatĂłanyagok behatolĂĄsĂĄt megkönnyĂtĆ anyagokat Ă©s korrĂłziĂłgĂĄtlĂłkat tartalmaznak.
A szuszpenziĂł koncentrĂĄtumokat ĂĄltalĂĄban Ășgy ĂĄllĂtjuk elĆ, hogy stabil, nem ĂŒlepedĆ, jĂłl folyĂł termĂ©ket kapjunk; ezek ĂĄltalĂĄban 10-75 sĂșly% hatĂłanyagot, 0,5-15 sĂșly % diszpergĂĄlĂłszert, 0,1-10 sĂșly% szuszpendĂĄlĂłszert, pĂ©ldĂĄul vĂ©dĆkolloidokat, 0-10 sĂșly% egyĂ©b adalĂ©kanyagot, pĂ©ldĂĄul habzĂĄsgĂĄtlĂłkat, korrĂłziĂłgĂĄtlĂłkat, stabilizĂĄlĂłszereket, a hatĂłanyag behatolĂĄsĂĄt Ă©s megtapadĂĄsĂĄt könnyĂtĆ anyagokat, valamint vizet vagy valamilyen szerves folyadĂ©kot tartalmaznak, amelyben a hatĂłanyag jĂłl oldĂłdik; bizonyos szerves, szilĂĄrd anyagok vagy szervetlen sĂłk is jelen lehetnek oldott ĂĄllapotban a formĂĄlt kĂ©szĂtmĂ©nyben, az ĂŒlepedĂ©s
189 269 kristĂĄlyos formĂĄban, op.: 184-186 âC (bomlĂĄs közben).
Elemzés: C21H12C1F3N4O7S.
SzĂĄmĂtott: C 45,3; H 2,2; N 10,1 %.
TalĂĄlt: C 45,1; H 2,0; N 10,0%.
meggĂĄtlĂĄsĂĄnak elĆsegĂtĂ©sĂ©re, vagy fagyĂĄsgĂĄtlĂłszerkĂ©nt a vĂz szĂĄmĂĄra.
A talĂĄlmĂĄny tĂĄrgyĂĄhoz tartoznak a vizes diszperziĂłk Ă©s emulziĂłk is, Ăgy pĂ©ldĂĄul a talĂĄlmĂĄny szerinti nedvesedĂ© por vagy koncentrĂĄtum hĂgĂtĂĄsĂĄval ka- 5 pott kĂ©szĂtmĂ©nyek is. Ezek az emulziĂłk lehetnek vĂz/olaj vagy olaj/vĂz tĂpusĂșak, Ă©s konszĂsztenciĂĄjuk lehet sƱrƱ, âmajonĂ©zâ-szerƱ.
A talĂĄlmĂĄny szerinti kĂ©szĂtmĂ©nyek egyĂ©b komponensekkel is összekeverhetĆk, pĂ©ldĂĄul olyan vegyĂŒ- 0 letekkel, amelyek peszticid, herbicid vagy fungicid hatĂĄsĂșak. A kĂ©szĂtmĂ©nyek összekeverhetĆk tovĂĄbbi inszekticid hatĂĄsĂș anyagokkal, kĂŒlönösen olyan vegyĂŒletekkel, melyek hatĂĄsmĂłdja eltĂ©rĆ, pĂ©ldĂĄul hatĂĄsuk gyorsabban beĂĄll mint a talĂĄlmĂĄny szerinti 3 vegyĂŒletekĂ©. Erre pĂ©ldakĂ©nt emlĂthetĆk a pyrethrum vagy a piretroid tĂpusĂș vegyĂŒletek, pĂ©ldĂĄul a permethrin, cypermethrin, deltamethrin Ă©s fenvalerate.
A talĂĄlmĂĄnyt rĂ©szletesen ismertetjĂŒk az alĂĄbb 20 következĆ pĂ©ldĂĄkban. A kiindulĂłanyagkĂ©nt felhasznĂĄlt szulfenamidokat az irodalombĂłl ismert mĂłdszerrel ĂĄllĂtottuk elĆ [J. Am. Chem. Soc. 63,
1920 (1941)].
I. példa
2-KlĂłr-N- { { [4~(trifluor-metoxi)-fenil]-[ (2nitro-fenil)-tio]-amino } -karbonil} -benzamid elĆĂĄllĂtĂĄsa 30 g (0,28 mĂłl) 2-klĂłr-benzoĂl-izocianĂĄt Ă©s 50 ml szĂĄraz toluol elegyĂ©t keverĂ©s közben hozzĂĄadjuk 60 g (0,18 mĂłl) N-[4-(trifluor-metoxi)-fenil]-2nitro-benzol-szulfenamid Ă©s 100 ml toluol elegyĂ©- 35 hez. E reakciĂł enyhĂ©n exoterm, a hĆmĂ©rsĂ©klet legfeljebb 35 °C-ig emelkedik. SzobahĆmĂ©rsĂ©kleten tartjuk 4 napon ĂĄt, utĂĄna - 5 °C-ra hƱtjĂŒk, az Ăgy kapott kristĂĄlymasszĂĄt hideg toluol alatt felaprĂtjuk, szƱrjĂŒk, elĆbb toluollal, majd hideg petrolĂ©ter- 40 rel (forrĂĄspontja 40-^60 âC) mossuk, Ă©s vĂĄkuumban 40 °C-on szĂĄrĂtjuk. Ăgy 89,3 g hozammal kapjuk a tiszta, cĂm szerinti termĂ©ket halvĂĄnysĂĄrga kristĂĄlyok formĂĄjĂĄban, op.: 155-158 âC (bomlĂĄs közben). 45
Elemzés: C2,H13C1F3N3O5 S.
SzĂĄmĂtott: C 49,3; H 2,6; N 8,2%.
TalĂĄlt: C 49,4; H 2,5; N 8,3%.
2. példa
2-KlĂłr-N- {{[4-(trifluor-metoxi)-fenil]~{(2,4dinitro-fenil)-tio]~amino ) -karbonil}-benzamid elĆĂĄllĂtĂĄsa 55
3,6 g (0,02 mĂłl) 2-klĂłr-benzoil-izocianĂĄtĂ©s 20 ml toluol elegyĂ©t keverĂ©s közben hozzĂĄadjuk 3,75 g (0,01 mĂłl) N-[4-(trifluor-metoxi)-fenil]-2,4-dinitrobenzol-szulfenamid Ă©s 30 ml szĂĄraz toluol elegyĂ©hez 60 szobahĆmĂ©rsĂ©kleten. EzutĂĄn 6 napon ĂĄt ĂĄllni hagyjuk, majd - 5 °C-ra hƱtjĂŒk, szƱrjĂŒk, a csapadĂ©kot hideg toluollal, majd hideg petrolĂ©terrel (forrĂĄspontja 40-60 °C) mossuk. Ăgy 5,25 g hozammal kapjuk a cĂm szerinti, tiszta termĂ©ket halvĂĄnysĂĄrga, 65
3. példa
N- { { [4-[ 2-klĂłr-4-( trifluor-metil)-fenoxi]-fenil]f (2-nitro-fenil)-tio]-amino }-karbonil }-2,6-difluor-benzamid elĆĂĄllĂtĂĄsa
1,0 g (0,0055 mĂłl) 2,6-difluor-benzoil-izocianĂĄt Ă©s 10 ml szĂĄraz diklĂłr-metĂĄn elegyĂ©t 5 perc alatt hozzĂĄadagoljuk keverĂ©s közben, szobahĆmĂ©rsĂ©kleten 2,2 g (0,005 mĂłl) N- { 4-(2-klĂłr-4-(trifluormetil)-fenoxi]-fenil} -2-nitro-benzoI-szulfenamid Ă©s 35 ml szĂĄraz diklĂF-metĂĄn oldatĂĄhoz. 24 Ăłra elmĂșltĂĄval a reakciĂłelegyet petrolĂ©terrel (forrĂĄspontja 40-60 âC) hĂgĂtjuk, Ă©s a csapadĂ©k formĂĄjĂĄban megjelenĆ nyerstermĂ©ket elkĂŒlönĂtjĂŒk. Ezt az anyagot Ă©ter Ă©s petrolĂ©ter elegyĂ©bĆl ĂĄtkristĂĄlyositva
2,8 g hozammal jutunk a cĂm szerinti vegyĂŒlethez, halvĂĄnysĂĄrga kristĂĄlyok alakjĂĄban, op.: 149-152âC.
Elemzés: C^H^CIFjNjOjS.
SzĂĄmĂtott: C 52,0; H 2,4; N 6,7%.
TalĂĄlt: C 52,1; H 2,3; N 6,8%.
4. példa
2-KlĂłr-N- {{ [4-(trifluor-metoxi)-fenil]-{ (2metil-fenil)-tio]-amino } -karbonil} -benzamid elĆĂĄllĂtĂĄsa
2,0 g (0,011 mĂłl) 2-klĂłr-benzoil-izocianĂĄt Ă©s 5 ml szĂĄraz toluol elegyĂ©t szobahĆmĂ©rsĂ©kleten, keverĂ©s közben hozzĂĄadjuk 3,0 g (0,01 mĂłl) N-[4-(trifluormetoxi)-fenil]-2-metil-benzol-szulfenamid Ă©s 40 ml 40-60 âC forrĂĄspontĂș szĂĄraz petrolĂ©ter elegyĂ©hez. NĂ©hĂĄny perc mĂșlva a reakciĂłelegy feltisztĂŒl, ezt követĆen kezd kivĂĄlni a cĂm szerinti termĂ©k olajos formĂĄban, Ă©s esetenkĂ©nt kristĂĄlyossĂĄ vĂĄlik. 24 Ăłra elmĂșltĂĄval a reakciĂłkeverĂ©ket - 5 âC-ra hƱtjĂŒk, szƱrjĂŒk, Ă©s a halvĂĄnyvörös termĂ©ket hideg petrolĂ©terrel mossuk. E nyerstermĂ©ket Ă©ter Ă©s petrolĂ©ter elegyĂ©bĆl ĂĄtkristĂĄlyosĂtva 3,3 g hozammal kapjuk a cĂm szerinti vegyĂŒletet tiszta, szĂntelen kristĂĄlyos formĂĄjĂĄban, op.: 79-80 âC.
Elemzés: C22H16CIF3N2O3S.
SzĂĄmĂtott: C 54,9; H 3,4; N 5,8%.
TalĂĄlt: C 54,6; H 3,3; N 6,1%.
5. példa
N- { { [ 4-KlĂłr-fenil]-[ 2-nitro-fenil)-tio] -amino }karbonil} -2,6-difiuor-benzamid elĆĂĄllĂtĂĄsa
1,8 g (0,01 mĂłl) 2,6-difluor-benzoil-izocianĂĄt Ă©s 15 ml szĂĄraz toluol elegyĂ©t 15 perc alatt keverĂ©s közben, szobahĆmĂ©rsĂ©kleten adagoljuk 2,8 g (0,01 mĂłl) N-(4-klĂłr-fenil)-2-nitro-benzol-szulfenamid Ă©s 35 ml szĂĄraz toluol oldatĂĄhoz. A keverĂ©ket Ă©jszakĂĄn ĂĄt ĂĄllni hagyjuk, ekkor azonban a reakciĂł mĂ©g nem teljes. NĂ©hĂĄny csepp trietil-amint . 189 269
Elemzés: Ci6H8C13F5N2O2S.
SzĂĄmĂtott: C 38,9, H 1,6, N 5,7%.
TatĂĄit: C 39,3, H 1,6, N 5,9%.
teszĂŒnk hozzĂĄ, Ă©s tovĂĄbbi 24 Ăłra mĂșlva â 5 °C-ra hĂŒtjĂŒk, szƱrjĂŒk, a halvĂĄnysĂĄrga csapadĂ©kot hideg toluollal mossuk. A toluol teljes eltĂĄvolĂtĂĄsa vĂ©gett a termĂ©ket 3 napon ĂĄt szĂĄrĂtjuk vĂĄkuumban, 40 âCon. Ăgy 3,1 g hozammal kapjuk a cĂm szerinti vegyĂŒletet, op.: 176-178âC.
Elemzés: C20H12ClF2N3O4S.
SzĂĄmĂtott: C 51,8 H 2,6, N 9,1%.
TalĂĄlt: C 51,8 H 2,5, N 9,1%.
6. pĂ©lda * 2,6-Difluor-N- { {[ (triklĂłr-rnetil)-tio]-[4-(trifluor-metil)-fenil]-amino }-karbonil }-benzamid elĆĂĄllĂtĂĄsa
2,0 g (0,011 mĂłl) 2,6-difluor-benzoil-izocianĂĄt Ă©s 15 ml szĂĄraz diklĂłr-metĂĄn oldatĂĄt keverĂ©s közben szobahĆmĂ©rsĂ©kleten hozzĂĄadjuk 3,1 g (0,01 mĂłl)
1,1,1 -triklĂłr-N-[4-(trifluor-metil)-fenil]-metĂĄnszulfenamid Ă©s 35 ml szĂĄraz diklĂłr-metĂĄn oldatĂĄhoz. 2 nap mĂșlva a reakciĂł mĂ©g nem teljes, ezĂ©rt tovĂĄbbi mennyisĂ©gƱ, 2,0 g izocianĂĄtot adunk hozzĂĄ. A teljes reakciĂł idĆtartama 28 nap: ekkor a reakciĂłelegyet 400 ml 40-60 âC forrĂĄspontĂș petrolĂ©terrel hĂgĂtjuk, Ă©s szƱrjĂŒk. A szƱrlet bepĂĄrlĂĄsĂĄval kapott 4,0 g maradĂ©kot szilikagĂ©len kromatografĂĄljuk, eluĂĄlĂĄshoz diklĂłr-metĂĄnt hasznĂĄlunk. Ăgy
1,3 g hozammal jutunk a szĂntelen kristĂĄlyok formĂĄjĂĄban megjelenĆ, tiszta cĂm szerinti vegyĂŒlethez, op.: 129-130âC.
7. példa
2-KlĂłr-N- { { [4-[2-klĂłr-4-( trifluor-metil)-fenoxi] fenil]-[ ( triklĂłr-rnetil)-tio)-amino } -karbonil } -benzamid elĆĂĄllĂtĂĄsa
3,6 g (0,02 mĂłl) 2-klĂłr-benzoil-izocianĂĄt Ă©s 15 ml szĂĄraz toluol elegyĂ©t 5 perc alatt keverĂ©s közben, szobahĆmĂ©rsĂ©kleten adagoljuk 4,0 g (0,009 mĂłl) 1,1,1-triklĂłr-N- {4-[2-klĂłr-4-(trifluor-metil)-feno15 xij-fenil} -metĂĄn-szulfenamid Ă©s 25 ml szĂĄraz toluol elegyĂ©hez. 10 nap elmĂșltĂĄval a reakciĂłelegyet 500 ml 40-60 âC forrĂĄspontĂș petrolĂ©terrel hĂgĂtjuk, Ă©s szƱrjĂŒk. A szƱrletet bepĂĄrolva egy nyers maradĂ©kot kapunk, ezt szilikagĂ©len gyorsan kromatogra20 fĂĄljuk, az eluĂĄlĂĄshoz diklĂłr-metĂĄnt hasznĂĄlunk. Ăgy a tiszta, cĂm szerinti vegyĂŒlethez jutunk, op.: 68-71 âC.
Elemzés: C22H12C15F3N2O3S.
SzĂĄmĂtott: C 42,7, H 1,9, N 4,5%.
TalĂĄlt: C 43,3, H 1,9, N 4,5%.
A fenti pĂ©ldĂĄkban leĂrt eljĂĄrĂĄsok segĂtsĂ©gĂ©vel tovĂĄbbi vegyĂŒleteket ĂĄllĂtottunk elĆ, ezek olvadĂĄspontjĂĄt Ă©s elemzĂ©si adatait a következĆ 1. TĂĄblĂĄzat foglalja össze.
1. TĂĄblĂĄzat (I) kĂ©pletƱ vegyĂŒletek
| PĂ©lda szĂĄma | (X)â- | R | Hal | B | op. C | ElemzĂ©si %) | |||
| C H. | N | ||||||||
| 8 | 4-Clâ | câh5 | F | F | 115-117 | SzĂĄm. | C2âHI3C1F2N2O2S | 57,3 3.1 | 6.7 |
| TĂĄl. | 57,3 3,2 | 7,2 | |||||||
| 9 | 4-Clâ | 2-CH3âCeH4 - | F | F | 125-128 | SzĂĄm. | C21H15C1F2N2O2S | 58,3 3,5 | 6.5 |
| TĂĄl. | 58,1 3,3 | 6.6 | |||||||
| 10 | 4-Clâ | 3-CHjâCâH4â | F | F | 140-142 | SzĂĄm. | C21H1SC1F2N2O2S | 58,3 3,5 | 1,5 |
| TĂĄl. | 58,5 3,3 | 6,6 | |||||||
| 11 | 4-Cl â | 4-CH3âC6H4â | F | F | 130-133 | SzĂĄm. | C21H,sC1F2N2O2S | 58,3 3,5 | 6,5 |
| TĂĄl. | 57,6 3,5 | 6.7 | |||||||
| 12 | 4-Cl â | 4-ClâCâH4â | F | F | 86-88 | SzĂĄm. | c2âh12ci2f2n2o2s | 53,0 2,6 | 6,2 |
| TĂĄl. | 52,9 2,7 | 6,3 | |||||||
| 13 | 4-Cl â | 2,4(NO2)2âC6H3 â | F | F | 171-173 | SzĂĄm. | C20HuC1F2N4O6S | 47,2 2,2 | 11.0 |
| TĂĄl. | 47,2 2,2 | 10.9 | |||||||
| 14 | 4-Clâ | C13Câ | F | F | 135-136 | SzĂĄm. | C,sH,C14F2N2O2S | 39,1 1,7 | 6.1 |
| TĂĄl. | 40,1 1,8 | 6,2 | |||||||
| 15 | 4-CF3- | c4H5 | F | F | 127-130 | SzĂĄm. | c21h13f5n2o2s | 55,8 2,9 | 6,2 |
| TĂĄl. | 55,5 2,9 | 6,6 | |||||||
| 16 | 4-CFjâ | 2-CH3âC6H4â | F | F | 120-123 | SzĂĄm. | ^22^ , ,F 5Î2Ξ2$ | 56,6 3,2 | 6,0 |
| TĂĄl. | 55,9 2.9 | 6,1 | |||||||
| 17 | 4-CF3â | 3-CH3âCâH4â | F | F | 150-153 | SzĂĄm. | C22H15FsN2O2S | 56,6 3,2 | 6,0 |
| TĂĄl. | 56,6 3,1 | 6,3 |
-5189 269
1. TĂĄblĂĄzat folytatĂĄsa
| PĂ©lda szĂĄma | (X)»â | R | Hal | B | bp. âC | ElemzĂ©st %) | |||
| C Î | Î | ||||||||
| 18 | 4-CFjâ | 4-CH3âCeH4â | F | F | 142-145 | SzĂĄm. TĂĄl. | CjjH1s<NjOjS | 56,6 3,2 56,3 3,0 | 6,0 6,3 |
| 19 | 4-CFjâ | 4-BrâCsH4â | F | F | 135-137 | SzĂĄm. TĂĄl. | Cj.H.jBrFjNjOjS | 47,5 2,2 47,5 2,1 | 5,3 5,5 |
| 20 | 4-CFjâ | 2-NOjâCâH4 | F | F | 115-118 | SzĂĄm. TĂĄl. | C31HuF5N3O4S | 50,7 2,4 51,1 2,4 | 8,5 8,4 |
| 21 | 4-CFjâ | 4-NOjâCeH4 | F | F | 109-112 | SzĂĄm. TĂĄl. | C21H,2F,N3O4S | 50,7 2,4 51,0 2,8 | 8,5 8,7 |
| 22 | 4-CFjâ | 2,4-(NO2)jâC6H3 | F | F | 143-145 | SzĂĄm. TĂĄl. | CjiH,,F5N4OeS | 46,5 2,0 46,4 2,0 | 10,3 10,3 |
| 23 | 4-CFjOâ | 4-CH3âC6H4â | Cl | H | 124-126 | SzĂĄm. TĂĄl. | C22H1ĂC1F3NjO3S | 54,9 3,4 54,8 3,1 | 5,8 5,8 |
| 24 | 4-CF3O- | 4-NOjâCeH4â | Cl | H | 177-178 | SzĂĄm. TĂĄl. | Cj,H13C1F3N3OjS | 49,3 2,6 49,1 2,4 | 8,2 7,8 |
| 25 | 4-CFjOâ | CljCâ | Cl | H | 97-99 | SzĂĄm. TĂĄl. | C,4H,CI4F3NjO3S | 37,8 1,8 38,6 1,7 | 5.5 5.6 |
| 26 | 4-CFj | 4-t-butil-CâH4 | F | F | 63-66 | SzĂĄm. TĂĄl. | CjjHj.FjNjOjS | 59,1 4,1 59,3 4,3 | 5,5 5,4 |
| 27 | 4-CFj | 4-C1âCeH4 | F | F | 144-146 | SzĂĄm. TĂĄl. | Cj.H.jCIF.NjOjS | 51,8 2,5 51,7 2,2 | 5.8 6.1 |
| 28 | 4-C1 | 4-NOjâCâH4 | F | F | 110-113 | SzĂĄm. TĂĄl. | CjoH.jCIFjNAS | 51,8 2,6 51,8 2,3 | 9,1 8,9 |
| 29 | 4-(2-Cl-4CF3âC6H30)â | CoH, | Cl | H | 55-58 | SzĂĄm. TĂĄl. | Cj7HnCljF3NjO3S | 56,2 2,9 55,4 2,9 | 4,9 4,8 |
| 30 | 4-(2-Cl-4- CF3-C6H3O)â | 4-CIâC6H4 | Cl | H | 93-95 | SzĂĄm. TĂĄl. | Cj7H16C13F3NjO3S | 53,0 2,6 53,2 2,6 | 4.6 4.7 |
| 31 | 4(20-4- CF3C6H3O)â | 2-CH3âC6H4 | Cl | H | 65-68 | SzĂĄm. TĂĄl. | C2,HâC12F3N2O3S | 56,8 3,2 57,6 3,2 | 4,8 4,8 |
| 32 | 4-CF3O | 2-izopropil- câH4 | Cl | H | 65-68 | SzĂĄm. TĂĄl. | Cj4H20CIF3NjO3S | 56,6 4,0 56,6 4,4 | 5,5 5,4 |
| 33 | 4-CF3O | 4-C1âC6H4 | Cl | H | 124-126 | SzĂĄm. TĂĄl. | C21H13CIjF3N2O3S | 50.3 2,6 50.4 2,6 | 5,6 6,0 |
| 34 | 4-(2-Cl-4- CF3-C6H3O)- | 4-CHjâC4H4 | Cl | H | 133-135 | SzĂĄm. TĂĄl. | Cj,Hi(,C12F3N2O3S | 56,8 3,2 56,6 3,2 | 4,8 4,7 |
| 35 | 4-(2-Cl-4. cf3-c6h30)- | 2-NOjâCâH4 | Cl | H | 136-138 | SzĂĄm. TĂĄl. | C27HleCl2F3N3O,S | 52,1 2,6 52,6 2,6 | 6,7 6,4 |
| 36 | 4-C1 | 4-t-butil-C6H4 | F | F | 93-96 | SzĂĄm. TĂĄl. | CjjHj.CIFjNjOjS | 60,7 4,4 59,6 4,2 | 5,9 5,6 |
| 37 | 4-C1 | 4-BrâCâH4 | F | F | 119-121 | SzĂĄm. TĂĄl. | C^H.jBrCIFjNjOjS | 48,3 2,4 48,6 2,5 | 5,6 5,9 |
| 38 | 3,5-Cl2-4- (4-NO2âCeH40)â | 2-NOjâC6H4 | F | F | 126-129 | SzĂĄm, TĂĄl. | Cj.H14C12F2N4O7S | 49,1 2,2 49,1 2,2 | 8,8 8,3 |
| 39 | 3,5-CI2-4- (4-NO2âCâH4O)â | 2-NOjâC4H4 | Cl | H | 123-126 | SzĂĄm. TĂĄl. | Î^Î,,Î,N40-,S | 49,3 2,4 49,6 2,4 | 8,8 8,4 |
| 40 | 4-CFjâ | 2-NOjâCâH4 | F | Cl | 177-178 | SzĂĄm. TĂĄl. | Cj,H12C1F4N3O4S | 49,1 2,4 48,8 2,1 | 8,2 8,0 |
| 41 | 3-CI-4-(4CNâC6H40)â | 2-NOâCeH4â | F | F | 139-141 | SzĂĄm. TĂĄl. | C27H1sC1F2N4O,S | 55.8 2,6 55.9 2,5 | 9.6 9.7 |
-6I
189 269 2
1. TĂĄblĂĄzat folytatĂĄsa
| PĂ©lda szĂĄma | (X)ââ | R | Hal | B | op. âC | ElemzĂ©st %) | ||||
| C H | N | |||||||||
| 42 | 3-Cl-4-(3- | 2-NO2- | - c6h4- | Cl | H | 137-138 | SzĂĄm. | C2,H1sC12F3N4O7S | 48,6 2,3 | 83 |
| CF3-4-NO2â C6H3O)- | TĂĄl. | 48,5 2,2 | 8,3 | |||||||
| 43 | 4-CF3CâH4Oâ | 2-NO2 | - câH4- | F. | F | 98-99 | SzĂĄm. | C21H13F5N4O5S | 47,7 2,5 | 10,6 |
| TĂĄl. | 47,7 2,5 | 10,3 |
39. példa
A talĂĄlmĂĄny szerinti vegyĂŒletek inszekticid hatĂĄsĂĄt a következĆ vizsgĂĄlatok segĂtsĂ©gĂ©vel ellenĆriztĂŒk.
datba, majd 48 Ăłra elmĂșltĂĄval a tĂșlĂ©lĆ lĂĄrvĂĄkat 15 szemcsĂ©s ĂĄllati takarmĂĄnnyal tĂĄplĂĄljuk; a pusztulĂĄs vĂ©gsĆ szĂĄzalĂ©kos Ă©rtĂ©kĂ©t akkor ĂĄllapĂtjuk meg, amikor az összes lĂĄrvĂĄk mĂĄr bebĂĄbozĂłdtak Ă©s Ă©rett rovarokkĂĄ alakultak, vagy elpusztultak.
1. vizsgĂĄlat
A talĂĄlmĂĄny szerinti vegyĂŒletek inszekticid Ă©s ovicid hatĂĄsĂĄt a következĆ rovarokon Ă©rtĂ©keltĂŒk: Spodoptera littoralis (a következĆkben: S. 1.), Aedes aegypti (A. a) Ă©s a Spodoptera littoralis petĂ©i (S. 1. ov.).
Az alĂĄbbiakban mutatjuk be az alkalmazott vizsgĂĄlati mĂłdszereket. Minden egyes esetben a rovarok szĂĄmĂĄra szokĂĄsos körĂŒlmĂ©nyek között (28 °C ± 20 âC; vĂĄltakozĂł fĂ©nyhatĂĄs Ă©s nedvessĂ©g) hajtjuk vĂ©gre a vizsgĂĄlatokat.
Minden vizsgĂĄlat esetĂ©ben kiszĂĄmĂtottuk a vegyĂŒlet LCS0 Ă©rtĂ©kĂ©t az elpusztĂtott rovarok szĂĄmĂĄbĂłl, Ă©s összehasonlĂtottuk az etil-paration ismert vegyĂŒlet alkalmazĂĄsa mellett ugyanezen vizsgĂĄlatoknĂĄl kapott LCS0 Ă©rtĂ©kekkel. Az eredmĂ©nyeket a toxicitĂĄsi index segĂtsĂ©gĂ©vel fejezzĂŒk ki.
ToxicitĂĄsi index =
LC50 (paration) LCS0 (vizsgĂĄlt vegyĂŒlet) x 100.
A kapott Ă©rtĂ©keket a 2. TĂĄblĂĄzatban tĂŒntetjĂŒk fel.
(i) Spodoptera littoralis
A vizsgĂĄlt vegyĂŒletek oldatĂĄt vagy szuszpenziĂłjĂĄt 10% acetont tartalmazĂł vĂzzel hĂgĂtjuk, mely 0,025% Triton XlOO-at [polietilĂ©n-glikol-mono-(pl-(l,l,3,3-tetrametilbutil)fenil-Ă©ter] tartalmaz. Ăgy koncentrĂĄciĂłsorozatot kĂ©szĂtĂŒnk, majd a kapott oldatokat egy logaritmikus permetezĆgĂ©p alkalmazĂĄsĂĄval olyan petri-csĂ©szĂ©kre permetezzĂŒk, melyet a Spodoptera littoralis lĂĄrvĂĄi szĂĄmĂĄra megfelelĆ tĂĄptalajt tartalmaznak. A permedĂ© megszĂĄradĂĄsa utĂĄn a csĂ©szĂ©ket tĂz, mĂĄsodik lĂĄrvaĂĄllapotĂș lĂĄrvĂĄval fertĆzzĂŒk. A permetezĂ©s utĂĄn 7 nappal ellenĆrizzĂŒk a rovarok pusztulĂĄsĂĄt.
(ii) A vizsgĂĄlandĂł vegyĂŒletekbĆl több, csökkenĆ koncentrĂĄciĂłjĂș oldatot (0,1 %-tĂłl lefelĂ© hĂgĂtva) kĂ©szĂtĂŒnk aceton segĂtsĂ©gĂ©vel; az oldatot az (i) pont szerint ĂĄllĂtjuk elĆ. EzekbĆl az oldatokbĂłl 100 mikroliternyi mennyisĂ©geket adunk 100 ml csapvĂzhez, majd az acetont elpĂĄrologtatjuk. TĂz, korai 4. lĂĄrvaĂĄllapotban lĂ©vĆ lĂĄrvĂĄt helyezĂŒnk a vizsgĂĄlati ol(iii) Spodoptera littoralis (ovicid hatĂĄs)
Nz oldatokat ugyanĂșgy kĂ©szĂtjĂŒk, ahogyan az (i) pontban leĂrtak. 24 ĂłrĂĄnĂĄl fiatalabb petĂ©ket kĂ©szĂ25 tĂŒnk elĆ a következĆk szerint: Ă©rett Spodoptera littoralis egyedeket nagy mƱanyag hengerekben tartunk, a hengerekben elhelyezett itatĂłspapĂrra a lepkĂ©k lerakjĂĄk petĂ©iket. MegközelĂtĆleg 60-70 petĂ©t tartalmazĂł rĂ©szeket vĂĄgunk le az itatĂłspapĂrbĂłl, 30 1 cm kerĂŒlettel. A petĂ©ket tartalmazĂł papĂrdarabokat a petĂ©kkel felfelĂ© 5 cm ĂĄtmĂ©rĆjƱ petri csĂ©szĂ©k alsĂł felĂ©ben lĂ©vĆ szƱrĆpapĂrra helyezzĂŒk, majd kĂŒlönbözĆ prĂłbaoldatokkal, illetve a kontrollkĂ©nt hasznĂĄlt oldattal permetezzĂŒk be a vizsgĂĄlati edĂ©35 nyĂ©k tartalmĂĄt. A csĂ©szĂ©ket fedve tartjuk mindaddig, amĂg a kontroli-petĂ©k kikelnek, az megközelĂtĆleg 5 napot vesz igĂ©nybe. Ezt követĆen szĂĄmĂtjuk ki az ovicid hatĂĄs következtĂ©ben beĂĄllĂł pusztulĂĄs szĂĄzalĂ©kos Ă©rtĂ©kĂ©ti
2. TĂĄblĂĄzat
A vegyĂŒletek ToxicitĂĄsi index
| példa szåma | Spodoptera littoralis | Aedes aegypti | Spodoptera littoralis ov. |
| 1 | 750 | 220 | 210 |
| 2 | 150 | 82 | 3300 |
| 3 | 4500 | - | 0 |
| 4 | 110 | 77 | 2200 |
| 5 | 90 | 220 | 0-4 |
| 6 | 260 | 34 | 400 |
| 7 | 1800 | 55 | 0 |
| 8 | 16 | 22 | 480 |
| 9 | 43 | 31 | 1400 |
| 10 | 20 | 24 | 1400 |
| 11 | 23 | 25 | 680 |
| 12 | 17 | 14 | - |
| 13 | 35 | 100 | 1800 |
| 14 | 10 | 6 | 560 |
| 15 | 170 | 50 | 1800 |
| 16 | 550 | - | 2700 |
| 17 | 260 | 160 | 2800 |
| 18 | 300 | 170 | 2300 |
_ 189 269
2. TĂĄblĂĄzat folytatĂĄsa
| A vegyĂŒletek pĂ©lda szĂĄma | Spodoptera littoralis | ToxieitĂĄsi index Aedes Spodoptera aegypti littoralis ov. | |
| 19 | 240 | 10 | 1500 |
| 20 | 160 | 180 | 1800 |
| 21 | 96 | 13 | |
| 22 | 220 | 51 | 2300 |
| 23 | 140 | 145 | 1500 |
| 24 | 54 | 31 | 11 |
| 25 | 140 | 28 | 1300 |
| 26 | 580 | 82 | 8 |
| 27 | 220 | 21 | 2200 |
| 28 | 54 | 6 | 720 |
| 29 | 930 | 330 | 0 |
| 30 | 670 | 220 | 0 |
| 31 | 960 | 240 | 0 |
| 32 | 88 | 28 | 2000 |
| 33 | 57 | 44 | 1300 |
| 34 | 1200 | 130 | 0 |
| 35 | 2500 | 82 | 0 |
| 36 | 42 | 22 | 0 |
| 37 | 51 | 26 | 850 |
| 38 | 330 | 30 | 0 |
| 39 | 460 | 52 | 0 |
| 40 | 180 | 130 | 0 |
| 41 | 230 | 79 | 0 |
| 42 | 330 | 28 | 0 |
| 43 | 21 | 4 | 0 |
40. példa
A talĂĄlmĂĄny szerinti vegyĂŒletek oldhatĂłsĂĄgĂĄt vizsgĂĄltuk xilolban, ami ĂĄltalĂĄnosan hasznĂĄlt formĂĄlĂł oldĂłszer. OldhatĂłsĂĄgi prĂłbĂĄkat vĂ©geztĂŒnk nĂ©hĂĄny talĂĄlmĂĄny szerinti vegyĂŒlettel Ă©s ezekhez szerkezetileg közelĂĄllĂł, ismert vegyĂŒlettel. A vizsgĂĄlati mĂłdszert alĂĄbb ismertetjĂŒk.
Az adott vegyĂŒletet (200 mg) egyensĂșlyi ĂĄllapotba hozzuk az oldĂłszerrel (0,5 ml o-xilol, 20 °C-on, sötĂ©t helyen, 48 ĂłrĂĄn ĂĄt). Az egyensĂșlyi ĂĄllapot beĂĄllĂtĂĄsa utĂĄn a felĂŒlĂșszĂł folyadĂ©kot eltĂĄvolĂtjuk, centrifugĂĄljuk, majd szƱrjĂŒk. EbbĆl egy alikvot rĂ©szt (0,1 ml) 1-100 ml tĂ©rfogatra töltĂŒnk acetonitrillel, majd összehasonlĂtĂł standard alkalmazĂĄsĂĄval folyadĂ©kkromatogrĂĄfiĂĄs vizsgĂĄlatot vĂ©gzĂŒnk.
Az igy kapott eredményeket az alåbbi tåblåzat szemlélteti.
| VegyĂŒletek | OldhatĂłsĂĄg, xilolban (g/liter) |
| A 838 286 szĂĄmĂș belga szabadalmi leĂrĂĄsban ismertetett l-[4-(4-trifluormetil-2-klĂłr-fenoxi)-fenil]-3-(2,6-difluor-benzoil)-karbamid | 5,7 |
FentiekbĆl kitƱnik, hogy a talĂĄlmĂĄny szerinti vegyĂŒletek (amelyek az ismert vegyĂŒletek szerkezetĂ©tĆl abban kĂŒlönböznek, hogy az anilincsoport nitrogĂ©natomjĂĄhoz 2-nitro-fenil-tio-csoport kapcsolĂłdik) jobban oldĂłdnak xilolban, mint az ismert vegyĂŒletek, Ă©s ennek következtĂ©ben formĂĄlhatĂłk.
Formålåsi példåk 1. példa
Por 0,1% hatĂłanyag tartalommal g 2-klĂłr-N-[[[4-(trifiuor-metoxi)-fenil [(2,4-dinitro-fenil)-tio]-amino]-karbonil]-benzamidot 20 g kaolinnal keverĂŒnk kalapĂĄcsos malomban. A keverĂ©khez tovĂĄbbi 1 kg kaolint adunk Ă©s az aprĂtĂĄst tovĂĄbb folytatjuk.
2. példa
EmulgeĂĄlhatĂł koncentrĂĄtum 20% hatĂłanyag tartalommal
200 g N-[[[4-[2-klĂłr-4-(trifluor-metil)-fenoxi]fenil] [(2-nitro-fenil)-tio]-amino]-karbonil]-2,6difluor-benzamidot lassan 200 g xilol, 200 g ciklohexanon Ă©s 100 g Tensiofix NF elegyĂ©hez adunk. Az elegyet keverjĂŒk, majd xilollal 1 literre töltjĂŒk fel (Tensiofix NF: kĂĄlcium-dodecil-benzol-szulfonĂĄt Ă©s nonil-fenol-etoxilĂĄt elegye).
3. példa
NedvesĂthetĆ por 90% hatĂłanyag tartalommal
100 g 2-klĂłr-N-([[4-(trifluor-metoxi)-fenil]-[(2nitro-fenil)-tio]-amino]-karbonil]-benzamidot kalapĂĄcsos malomban 20 g Empicol LZ-vel, 30 g Orotan 731-gyei Ă©s 50 g kaolinnal elkeverĂŒnk. A kapott elegyet malomban keverjĂŒk Ă©s porĂtjuk. (Empicol LZ: nĂĄtrium-lauril-szulfĂĄt); (Orotan 731: diizobutilĂ©n-maleinsavanhidrid-kopolimer).
OldhatĂłsĂĄgi adatok
OldhatĂłsĂĄg,
VegyĂŒletek xilolban _(g/hter)
Az 1. pĂ©lda szerinti vegyĂŒlet 3,7
A 2 601 780 szĂĄmĂș NSZK-beli szabadalmi leĂrĂĄsban ismertetett l-[4(trifluor-metoxi)-fenil]-3-(2-klĂłrbenzoil)-karbamid 2,3
A 3. pĂ©lda szerinti vegyĂŒlet 18,8
Claims (2)
1. Inszekticid kĂ©szĂtmĂ©ny, amelyben szilĂĄrd vagy folyĂ©kony hordozĂłanyag, Ăgy cĂ©lszerƱen kaolin vagy xilol Ă©s ciklohexĂĄn, tovĂĄbbĂĄ adott esetben felĂŒletaktĂv anyag, Ăgy cĂ©lszerƱen nĂĄtrium-laurilszulfĂĄt van, azzal jellemezve, hogy a kĂ©szĂtmĂ©ny hatĂłanyagkĂ©nt 0,1-95 sĂșly %-ban (I) ĂĄltalĂĄnos kĂ©pletƱ benzoil-fenil-karbamid-szĂĄrmazĂ©kokat - a kĂ©pletben
Hal jelentése halogénatom,
189 269
B jelentése hidrogén- vagy halogénatom,
X jelentĂ©se halogĂ©natom, trifluor-metil-, trifluormetoxi-csoport, tovĂĄbbĂĄ nitro-, ciano- vagy trifluor-metil-csoporttal vagy halogĂ©natommal egyszeresen vagy kĂ©tszeresen helyettesĂtett fenoxicsoport, n Ă©rtĂ©ke 1, 2 vagy 3,
R jelentĂ©se 1-4 szĂ©natomos halogĂ©n-alkilcsoport vagy adott esetben egy vagy kĂ©t nitrocsoporttal vagy 1-6 szĂ©natomos alkilcsoporttal vagy halogĂ©natommal egyszeresen helyettesĂtett fenilcsoport - tartalmaznak.
2. EljĂĄrĂĄs az (I) ĂĄltalĂĄnos kĂ©pletƱ benzoil-fenilkarbamid szĂĄrmazĂ©kok elĆĂĄllĂtĂĄsĂĄra, a kĂ©pletben
Hal jelentése halogénatom,
B jelentése hidrogén- vagy halogénatom,
XjelentĂ©se halogĂ©natom, trifluor-metil-, trifluormetoxi-csoport, tovĂĄbbĂĄ nitro- vagy ciano-, trifluor-metil-csoporttal vagy halogĂ©natommal egyszeresen vagy kĂ©tszeresen helyettesĂtett fenoxicsoport, 5 n Ă©rtĂ©ke 1, 2 vagy 3,
R jelentĂ©se 1-4 szĂ©natomos halogĂ©n-alkilcsoport vagy adott esetben egy vagy kĂ©t nitrocsoporttal vagy 1-6 szĂ©natomos alkilcsoporttal vagy halogĂ©natommal egyszeresen helyettesĂtett fenil10 csoport - azzal jellemezve, hogy (II) ĂĄltalĂĄnos kĂ©pletƱ benzoil-izocianĂĄtot - a kĂ©pletben B Ă©s Hal jelentĂ©se a tĂĄrgyi körben megadottal azonos - (III) ĂĄltalĂĄnos kĂ©pletƱ szulfenamiddal - a kĂ©pletben X, n Ă©s R jelentĂ©se a tĂĄrgyi körben megadottal azonos 15 - reagĂĄltatunk.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8211783 | 1982-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189269B true HU189269B (en) | 1986-06-30 |
Family
ID=10529898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU831393A HU189269B (en) | 1982-04-23 | 1983-04-21 | Pesticide compositions containing benzoyl-phenyl-car-bamide derivatives and process for preparing the active substances |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4497822A (hu) |
| JP (1) | JPS58189157A (hu) |
| KR (1) | KR840004716A (hu) |
| AU (1) | AU555722B2 (hu) |
| BE (1) | BE896547A (hu) |
| BR (1) | BR8302038A (hu) |
| CA (1) | CA1190246A (hu) |
| CH (1) | CH653992A5 (hu) |
| CS (1) | CS286383A2 (hu) |
| DD (1) | DD215003A5 (hu) |
| DE (1) | DE3314383A1 (hu) |
| DK (1) | DK176583A (hu) |
| ES (1) | ES8406433A1 (hu) |
| FI (1) | FI831370L (hu) |
| FR (1) | FR2525594A1 (hu) |
| GR (1) | GR78836B (hu) |
| HU (1) | HU189269B (hu) |
| IL (1) | IL68454A0 (hu) |
| IT (1) | IT1170133B (hu) |
| LU (1) | LU84763A1 (hu) |
| NL (1) | NL8301384A (hu) |
| NO (1) | NO831411L (hu) |
| OA (1) | OA07405A (hu) |
| PL (1) | PL241584A1 (hu) |
| PT (1) | PT76581B (hu) |
| SE (1) | SE8302263L (hu) |
| TR (1) | TR21543A (hu) |
| ZA (1) | ZA832808B (hu) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105085326B (zh) * | 2015-09-14 | 2017-04-19 | ć€©æŽ„ććŠéą | ć«ææ°šćșçČé žé Żćșç»æçèŻçČé °èČç±»ććç©ćć¶ć€æčæłćæè«ćșçš |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1572673A (hu) * | 1967-06-26 | 1969-06-27 | ||
| US4013717A (en) * | 1970-05-15 | 1977-03-22 | U.S. Philips Corporation | Benzoyl phenyl urea derivatives having insecticidal activities |
| DE2601780B2 (de) * | 1976-01-20 | 1979-07-26 | Bayer Ag, 5090 Leverkusen | N-Phenyl-N'-benzoylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| US4308213A (en) * | 1979-04-16 | 1981-12-29 | American Cyanamid Company | Meta-(phenylalkoxy)phenyl-N-methoxy-N-methylurea compounds |
| DE3032327A1 (de) * | 1980-08-27 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | N-sulfenylierte harnstoffe, verfahren zu ihrer herstellung, diese enthaltende fungizide mittel und ihre verwendung |
-
1983
- 1983-03-24 CA CA000424351A patent/CA1190246A/en not_active Expired
- 1983-04-14 US US06/484,773 patent/US4497822A/en not_active Expired - Fee Related
- 1983-04-20 NL NL8301384A patent/NL8301384A/nl not_active Application Discontinuation
- 1983-04-20 KR KR1019830001665A patent/KR840004716A/ko not_active Application Discontinuation
- 1983-04-20 BR BR8302038A patent/BR8302038A/pt not_active IP Right Cessation
- 1983-04-21 DD DD83250084A patent/DD215003A5/de unknown
- 1983-04-21 LU LU84763A patent/LU84763A1/de unknown
- 1983-04-21 TR TR21543A patent/TR21543A/xx unknown
- 1983-04-21 DE DE19833314383 patent/DE3314383A1/de not_active Withdrawn
- 1983-04-21 ES ES521693A patent/ES8406433A1/es not_active Expired
- 1983-04-21 SE SE8302263A patent/SE8302263L/ not_active Application Discontinuation
- 1983-04-21 FI FI831370A patent/FI831370L/fi not_active Application Discontinuation
- 1983-04-21 JP JP58069342A patent/JPS58189157A/ja active Granted
- 1983-04-21 FR FR8306567A patent/FR2525594A1/fr active Granted
- 1983-04-21 AU AU13847/83A patent/AU555722B2/en not_active Ceased
- 1983-04-21 GR GR71156A patent/GR78836B/el unknown
- 1983-04-21 ZA ZA832808A patent/ZA832808B/xx unknown
- 1983-04-21 PL PL24158483A patent/PL241584A1/xx unknown
- 1983-04-21 DK DK176583A patent/DK176583A/da not_active IP Right Cessation
- 1983-04-21 HU HU831393A patent/HU189269B/hu not_active IP Right Cessation
- 1983-04-21 NO NO831411A patent/NO831411L/no unknown
- 1983-04-21 OA OA57975A patent/OA07405A/xx unknown
- 1983-04-21 PT PT76581A patent/PT76581B/pt unknown
- 1983-04-21 IT IT20725/83A patent/IT1170133B/it active
- 1983-04-21 CH CH2152/83A patent/CH653992A5/de not_active IP Right Cessation
- 1983-04-21 IL IL68454A patent/IL68454A0/xx not_active IP Right Cessation
- 1983-04-21 CS CS832863A patent/CS286383A2/cs unknown
- 1983-04-22 BE BE0/210616A patent/BE896547A/nl not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |