CS220800B2 - Herbicide means and method of making the active substances - Google Patents
Herbicide means and method of making the active substances Download PDFInfo
- Publication number
- CS220800B2 CS220800B2 CS805584A CS558480A CS220800B2 CS 220800 B2 CS220800 B2 CS 220800B2 CS 805584 A CS805584 A CS 805584A CS 558480 A CS558480 A CS 558480A CS 220800 B2 CS220800 B2 CS 220800B2
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- CS
- Czechoslovakia
- Prior art keywords
- oxy
- active ingredient
- carbon atoms
- composition according
- group
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims description 12
- 239000013543 active substance Substances 0.000 title description 10
- 239000004009 herbicide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000460 chlorine Substances 0.000 claims description 268
- 239000000203 mixture Substances 0.000 claims description 44
- 239000004480 active ingredient Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- -1 alkali metal cation Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
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- 150000002431 hydrogen Chemical group 0.000 claims description 5
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- 239000005645 nematicide Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
PĆedloĆŸenĂœ vynĂĄlez se tĂœkĂĄ herbicidnĂho prostĆedku, kterĂœ obsahuje jako ĂșÄinnou sloĆŸku novĂ© .derivĂĄty 5-(pyridyl-2â-oxy)-2-nitrobĂ©nzoovĂ© kyseliny. DĂĄle se vynĂĄlez tĂœkĂĄ zpĆŻsobu vĂœroby tÄchto novĂœch derivĂĄtĆŻ kyseliny s herbicidnĂm ĂșÄinkem, jakoĆŸ i jejich pouĆŸitĂ jako herbicidĆŻ, pĆedevĆĄĂm selektivnĂch herbicidĆŻ v kulturĂĄch uĆŸitkovĂœch rostlin.
DerivĂĄty 5- (pyridy l-2â-oxy) -2-nitrobenzoovĂ© kyseliny jsou novĂœmi slouÄeninami. Z americkĂ©ho patentnĂho spisu Ä. 3 928 416 a DOS 2 753 900 jsou znĂĄmĂ© derivĂĄty 3-(p-trifluormethylfenoxy)-6-nitrobenzoovĂ© kyseliny s herbicidnĂm ĂșÄinkem. DĂĄle jsou v americkĂ©m patentnĂm spisu Ä. 4 031 131 popsĂĄny herbicidnĂ 3- (p-trifluormethylfenoxy JbenzoovĂ© kyseliny a jejich derivĂĄty a koneÄnÄ jsou ĆŸ americkĂ©ho patentnĂho spisu Ä. 3 784 635 znĂĄmĂ© herbicidnÄ ĂșÄinnĂ© derivĂĄty 3-( fenoxy ) -6-nitrobenzoovĂ© kyseliny.
DerivĂĄty 5- (pyridyl-2â-oxy) -2-nitrobenzoovĂ© kyseliny odpovĂdajĂ obecnĂ©mu vzorci I
v nÄmĆŸ
X znamenĂĄ halogen nebo halogenmethylovou skupinu,
Y znamenĂĄ vodĂk, halogen nebo halogenmethylovou skupinu,
A znamenĂĄ kyanoskupinu, zbytek âCOB nebo popĆĂpadÄ methylovou skupinou jednou nebio nÄkolikrĂĄte substituovanou 2-oxazolinovou skupinu,
Đ znamenĂĄ zbytek âOR1; âSR2, âNHoR4 nebo -ON=C(R5)2,
Ri znamenĂĄ vodĂk, kationt alkalickĂ©ho kovu, alkylovou skupinu s 1 aĆŸ 8 atomy uhlĂku, kterĂĄ je popĆĂpadÄ substituovĂĄna halogenem, kyanoskupinou, alkoxyskupinou ,s 1 aĆŸ 4 atomy uhlĂku, aĂlkoxykaTbonylovou skupinou s 1 aĆŸ 4 atomy uhlĂku v alkoxylovĂ© ÄĂĄsti nebo dialkyraminoskupinou s 1 aĆŸ 4 atomy uhlĂku v alkylech, dĂĄle znamenĂĄ alkenyliovou skupinu .se 3 aĆŸ 6 atomy uhlĂku, alkinyllovou skupinu se 3 aĆŸ 6 atomy uhlĂku, cykloalkylovou skupinu se 3 aĆŸ 6 atomy uhlĂku nebo fenylovĂœ nebo benzylovĂœ zbytek, kterĂœ j<e popĆĂpadÄ substituovĂĄn halogenem,
R2 znamenĂĄ alkylovou skupinu s 1 aĆŸ 6 atomy uhlĂku, kterĂĄ je popĆĂpadÄ substituovĂĄna alkoxykairbonylovou skupinou s 1 aĆŸ 4 atomy uhlĂku v allkoxylovĂ© ÄĂĄsti, dĂĄle zna menĂĄ 'alkanylovou .skupinu se 2 <aĆŸ 4 atomy uhlĂku nebo benzylovou skupinu,
R3 a R4 znamenajĂ nezĂĄvisle na sobÄ vodĂk nebo· allkylovou skupinu s 1 aĆŸ 4 atomy uhlĂku, kterĂĄ je popĆĂpadÄ substituovĂĄna kyanoskupinou nebo alkoxyskupinou s 1 aĆŸ 4 atomy uhlĂku, nebo jeden ze substituentĆŻ,
R3 a R4 znamenĂĄ takĂ© alkoxyskupinu s 1 aĆŸ 4 atomy uhlĂku ndbo alkylsulfonylovou skupinu s 1 aĆŸ 4 atomy uhlĂku a
R5 znamenĂĄ alkylovou skupinu s 1 aĆŸ 4 atomy uhlĂku.
Ve vzorci I se halogenem rozumĂ fluor, chlor, brom nebo jĂłd.
VĂœraz âalkylâ samotnĂœ nebo jako ÄĂĄst isubstituentu zahrnuje rozvÄtvenĂ© nebo nerozvÄtvenĂ© alkylovĂ© skupiny s uvedenĂœm poÄtem latomĆŻ uhlĂku. Jako pĆĂklady tÄchto skupin lze uvĂ©st skupinu methylovou, ethylovou, propyiovou, isopropylovou, butylovou, isobutylovou, sek.butylovou, terÄ.butylovou, jakoĆŸ i vyĆĄĆĄĂ homology, tj. .skupinu amylovou, isoamylovou, hexylbvou, heptylovou, oktylovou atd. vÄetnÄ jejich isomerĆŻ.
AlkenylovĂ© a alkinylovĂ© skupiny zahrnujĂ rovnÄĆŸ rozvÄtvenĂ© a nerozvÄtvenĂ© zbytky, kterĂ© obsahujĂ uvedenĂœ poÄet atomĆŻ uhlĂku a alespoĆ jedno nenasycenĂ© mĂsto. VĂœhodnĂœmi alkenylovĂœmi skupinami jsou popĆĂpadÄ halogenem substituovanĂ© allylovĂ©, methallylovĂ© a n-.butenylovĂ© Skupiny. VĂœhodnĂœmi alkinylovĂœmi skupinami je skupina propinylovĂĄ nebo propargylovĂĄ.
CykloalkylovĂœmi zbytky jsou zbytek cyklopnopylovĂœ, cyklobutylovĂœ, cyklopentylo-vĂœ, cyklohexylovĂœ a cykloheptylovĂœ. CykloalkenĂœlovĂ© zbytky odpovĂdajĂ tÄmto kruhovĂœm systĂ©mĆŻm, mohou vĆĄak jeĆĄtÄ vedle toho, vĆŸdy podle moĆŸnosti, obsahovat jednu nebo nÄkolik dvojnĂœch vazeb.
SlouÄeniny vzorce I majĂ vyslovenÄ selektivnĂ herbicidnĂ vlastnosti obecnÄ a ukĂĄzaly se jako zvlĂĄĆĄtÄ vĂœhodnĂ© Đș potĂrĂĄnĂ plevelĆŻ v kulturĂĄch uĆŸitkovĂœch rostlin, zejmĂ©na v kulturĂĄch sĂłji, bavlnĂku, obilovin, rĂœĆŸe, kukuĆice a cukrovĂ© Ćepy.
PĆi dostateÄnÄ vysokĂ©m aplikovanĂ©m mnoĆŸstvĂ majĂ vĆĄak tyto slouÄeniny takĂ© totĂĄlnĂ herbicidnĂ ĂșÄinek. Aplikace se mĆŻĆŸe provĂĄdÄt jak preemergentnÄ, tak i postemergentnÄ. PĆitom mohou aplikovanĂĄ mnoĆŸstvĂ kolĂsat v ĆĄirokĂœch mezĂch, napĆĂklad mezi 0,1 a 10 kg ĂșÄinnĂ© lĂĄtky na 1 ha, vĂœhodnÄ vĆĄak se pouĆŸĂvĂĄ 0,5 aĆŸ 5 kg ĂșÄinnĂ© lĂĄtky na 1 ha.
Velmi dobrĂ©ho ĂșÄinku proti plevelĆŻm v kulturĂĄch pĆĄenice, rĂœĆŸe nebo/a sĂłji bylo dosaĆŸeno za pouĆŸitĂ tÄch slouÄenin, kterĂ© strukturnÄ nĂĄleĆŸĂ do nĂĄsledujĂcĂch skupin:
ŃĐŸĐČ
(Ic)
V tÄchto slouÄeninĂĄch mĆŻĆŸe mĂt symbol Đ obecnÄ kaĆŸdĂœ z vĂœznamĆŻ, kterĂœ je definovĂĄn pod .vzorcem I. NejĆŻÄinnÄjĆĄĂ byly slouÄeniny, ve kterĂœch symbol Đ znamenĂĄ hydroxylovou skupinu, alkoxyskupinu s 1 aĆŸ 8 atomy uhlĂku, kyanalkoxyskupinu .s 1 aĆŸ 4 atomy uhlĂku v ĂĄlkoxyskupinÄ, alkoxykarbonylalkylovou skupinu <se 3 aĆŸ 13 atomy uhlĂku, dialkylaminoĂĄlkylOvou skupinu s 1 aĆŸ 4 atomy uhlĂku v alkylech, alkenyloxyskupinu se 3 aĆŸ 6 atomy uhlĂku, alkinyloxyskupinu se 3 aĆŸ 6 atomy uhlĂku, ĂĄlkylthioskupinu s 1 aĆŸ 6 atomy uhlĂku, alkoxykarbonylalkylthioskupinu se 3 aĆŸ 11 atomy uhlĂku, alkenylthioskupinu se 2 aĆŸ 4 atomy uhlĂku, alkylaminoskupinu s 1 aĆŸ 4 atomy uhlĂku, alkoxyalkylaminoskupinu se 2 aĆŸ 8 atomy uhlĂku, N-alkoxy-N-ialkylaminoskUplnu s 1 aĆŸ 4 atomy uhlĂku v alkylech.
ProstĆedky podle vynĂĄlezu obsahujĂ kromÄ ĂșÄinnĂ© lĂĄtky vzorce I vhodnou nosnou lĂĄtku nebo/a dalĆĄĂ pĆĂsady. VhodnĂ© nosnĂ© lĂĄtky a pĆĂpady mohou bĂœt pevnĂ© nebo kapalnĂ© a odpovĂdajĂ lĂĄtkĂĄm, kterĂ© se obvykle pouĆŸĂvajĂ pĆi pĆĂpravÄ takovĂœchto prostĆedkĆŻ, jako jsou napĆĂklad pĆĂrodnĂ nebo regenerovanĂ© minerĂĄlnĂ lĂĄtky, rozpouĆĄtÄdla, Ćedidla, dlspergĂĄtory, emulgĂĄtory, smĂĄÄeÄla, !adhezĂva, zahuĆĄĆ„ovadla, pojidla nebo/a hnojivĂĄ.
' Za ĂșÄelem pouĆŸitĂ v herbicidnĂch prostĆedcĂch lze slouÄeninu vzorce I zpracovĂĄvat obvyklĂœm zpĆŻsobem jako popraĆĄ, emulznĂ koncentrĂĄt, jako granulĂĄt, disperzi nebo takĂ© jako roztok nĂ©bo suspenzi obvyklĂœm zpĆŻsobem.
ProstĆedky podle vynĂĄlezu se vyrĂĄbÄjĂ o sobÄ znĂĄmĂœm /zpĆŻsobem dĆŻkladnĂœm smĂsenĂm a 'rozemletĂm ĂșÄinĂœch lĂĄtek obecnĂ©ho vzorce I s vhodnĂœmi nosnĂœmi lĂĄtkami nebo/a dispergĂĄtory, popĆĂpadÄ za pĆĂdavku prostĆedkĆŻ proti pÄnÄnĂ, smĂĄÄedel, dispergĂĄtorĆŻ nebo/a rozpouĆĄtÄdel, kterĂ©ĆŸto lĂĄtky jsou inertnĂ vĆŻÄi ĂșÄinnĂœm lĂĄtkĂĄm. ĂÄinnĂ© lĂĄtky se mohou vyskytovat a aplikovat v nĂĄsledujĂcĂch formĂĄch zpracovĂĄnĂ:
pevnĂ© formy zpracovĂĄnĂ:
popraĆĄ, posyp, granulĂĄt, obalovanĂœ granulĂĄt, itopregnovanĂœ granulĂĄt a homogennĂ granulĂĄt;
ve vodÄ dispergoviatelnĂ© koncentrĂĄty ĂșÄinnĂ© 'lĂĄtky:
smĂĄÄiteLnĂœ prĂĄĆĄek, pasta, emulze, emulznĂ koncentrĂĄty;
kapalnĂ© formy zpracovĂĄnĂ:
roztoky.
Koncentrace ĂșÄinnĂœch lĂĄtek ÄinĂ v prostĆedcĂch podle vynĂĄlezu 1 aĆŸ 80 % hmotnostnĂch a pĆi aplikaci se mohou popĆĂpadÄ pouĆŸĂvat takĂ© niĆŸĆĄĂ koncentrace, jako asi 0,05 aĆŸ 1 °/o.
Đ popsanĂœm prostĆedkĆŻm podle vynĂĄlezu se dajĂ pĆimĂchĂĄvat dalĆĄĂ biocidnÄ ĂșÄinnĂ© lĂĄtky nebo prostĆedky. Tak mohou novĂ© prostĆedky kromÄ uvedenĂœch slouÄenin obecnĂ©ho vzorce I obsahovat napĆĂklad insekticidy, fungicidy, baktericidy, fungistatika, bakteriostatika, nematocidy nebo dalĆĄĂ herbicidy za ĂșÄelem rozĆĄĂĆenĂ ĂșÄinnostnĂho spektra.
Podle vynĂĄlezu se slouÄeniny obecnĂ©ho vzorce I vyrĂĄbÄjĂ tĂm, ĆŸe se v aprotickĂ©m rozpouĆĄtÄdle, v pĆĂtomnosti bĂĄze v mnoĆŸstvĂ vĂĄzajĂcĂm kyselinu, nechĂĄ reagovat 2-halogenpyridin obecnĂ©ho vzorce II
v nÄmĆŸ
Hal znamenĂĄ atom halogenu a
X a Y majĂ vĂœznam uvedenĂœ pod vzorcem
I, s derivĂĄtem 3-hydroxybenzoovĂ© kyseliny obecnĂ©ho vzorce IV v nÄmĆŸ
A mĂĄ vĂœznam uvedenĂœ pod vzorcem I, a zĂskanĂœ derivĂĄt 5- (pyridyl-2â-oxy) benzoovĂ© kyseliny obecnĂ©ho vzorce V
v nÄmĆŸ
Đ, X a Y majĂ vĂœznam uvedenĂœ pod vzorcem I, se nitruje nitraÄnĂ /smÄsĂ.
Reakce se provĂĄdÄjĂ pĆi teplotĂĄch od 0 °C do teploty 150 °C. Jako rozpouĆĄtÄdla jsou vhodnĂĄ pĆedevĆĄĂm aprotickĂĄ rozpouĆĄtÄdla, jako dimethylsulfoxid, dimethylfoirmamid, sulfolan, N-methylpyrrolidon atd.
Jako bĂĄze, kterĂ© se pĆidĂĄvajĂ za ĂșÄelem vĂĄzĂĄnĂ odĆĄtÄpenĂ©ho atomu halogenu, se hodĂ jak anorganickĂ© bĂĄze, jako hydroxidy alkalickĂœch kovĆŻ, uhliÄitany alkalickĂœch kovĆŻ a kovĆŻ alkalickĂœch zemin, hydrogenuhliÄitany alkalickĂœch kovĆŻ a kovĆŻ alkalickĂœch zemin, tak i organickĂ© bĂĄze, jako napĆĂklad allkylaminy, dimethylamin, trimethylamin, diethĂœlamin, triethylamin atd.
Jako nitraÄnĂ roztoky pĆichĂĄzejĂ v Ășvahu smÄsi duisiÄnĂ© a sĂrovĂ© kyseliny, roztoky dusiÄnĂ© kyseliny v ledovĂ© kyselinÄ octolvĂ© nebo samotnĂĄ koncentrovanĂĄ dusiÄnĂĄ kyselina napĆĂklad v chlorovanĂœch uhlovodĂcĂch. Nitrace se provĂĄdÄjĂ pĆi teplotĂĄch kolem 0 °C aĆŸ do teploty mĂstnosti.
SlouÄeniny vzorce I jsou stĂĄlĂœmi slouÄeninami, kterĂ© jsou pro teplokrevnĂ© mĂĄlo jedovatĂ© a manipulace s nimi nevyĆŸaduje ĆŸĂĄdnĂœch bezpeÄnostnĂch opatĆenĂ. Tyto slouÄeniny j|sou relativnÄ dobĆe rozpustnĂ© v obvyklĂœch rozpouĆĄtÄdlech a ĆĄpatnÄ rozpustnĂ© ve vodÄ.
V nĂĄsledujĂcĂch pĆĂkladech se blĂĆŸe objasĆuje vĂœroba derivĂĄtĆŻ 5-(pyridyl-2â-yioxy]-3-nitrobenzoovĂ© kyseliny vzorce I podle vy nĂĄlezu. DalĆĄĂ slouÄeniny, -kterĂ© se dajĂ vyrobit analogickĂœm -zpĆŻsobem, jsou uvedeny v nĂĄsledujĂcĂ tabulce. Teploty jsou udĂĄvĂĄny ve stupnĂch Celsia, dĂly a procenta Jsou pĆedstavovĂĄny dĂly a procenty hmotnostnĂmi. Ădaje tlaku jsou -v Pa.
PĆĂklad 1
5-(3â-cl^l^i^ir-5â-ltrifluormethylpyridyl-2*-oxy) -2-nitrobenizoovĂĄ kyselina
Cl COOH
F^C 0 °z
8,4 g 5-(3â-chlor-5â-trifluormethylpyridyl-2â-oxy) benzoovĂ© kyseliny se -suspenduje ve 100 -ml -ethylenchloridu a suspenze -se ochladĂ. PĆi teplotÄ 0 °C se postupnÄ pĆikape 18 mililitrĆŻ koncentrovanĂ© sĂrovĂ© kyseliny a
1,5 ml 100% dusiÄnĂ© kyseliny rozpuĆĄtÄnĂ© v 2,5 ml sĂrovĂ© kyseliny. ReakÄnĂ smÄs se mĂchĂĄ 2 hodiny pĆi -teplotÄ mĂstnosti a potom -se vylije na 100- m'l ledovĂ© vody. OrganickĂĄ fĂĄze -se oddÄlĂ, vodnĂĄ fĂĄze se extrahuje ethylenchloridem, ethylenchloridovĂĄ fĂĄze se vysuĆĄĂ -sĂranem hoĆeÄnatĂœm a odpaĆĂ -se. Zbytek se -smĂsĂ s petroletherem a nechĂĄ se vykrystalovat OdfiltrovĂĄnĂm -se -zĂskĂĄ 5,6 g (60 % teorie) titulnĂ slouÄeniny o teplotÄ tĂĄnĂ 114 aĆŸ 117 °C.
5- (3â-chlor-5â-tri,f luormethylpyridyl-2â-oxy)be,nzoovĂĄ kyselina, kterĂĄ je nutnĂĄ jako -vĂœchozĂ lĂĄtka, se vyrobĂ nĂĄsledujĂcĂm zpĆŻsobem:
a) K -suspenzi 2 g hydridu -sodnĂ©ho (0,084 mol) v 50 ml -dimethylsulf oxidu se pĆikape 5,8 g 3-hydroxybenzoovĂ© kyseliny (0,042 mol) rozpuĆĄtÄnĂ© v 15 ml - dimethylsulfoxidu. KdyĆŸ -se veĆĄkerĂœ hydrid sodnĂœ rozpustĂ, pĆikape ise 8,3 g 2-fluor-3-chlor-5-trifluormethylpyiridinu, kterĂœ je rozpuĆĄtÄn v 10 ml dimethylsulfoxidu. Teplota se pĆitom zvĂœĆĄĂ na 45 °C. Po 6 hodinĂĄch mĂchĂĄnĂ pĆi teplotÄ 85 stupĆĆŻ Cel-sia je reakce ukonÄena. Dlmethylsulfoxid se odpaĆĂ ve vakuu -a zbytek se vylije na ledovou vodu. PĆi okyselenĂ koncentrovanou chlorovodĂkovou kyselinou se tvoĆĂ sraĆŸenina. Tato -sraĆŸenina se odfiltruje a promyje se vodou. Po pĆekrystalovĂĄnĂ ze -smÄsi ethanolu a vody se zĂskĂĄ 8,4 g - (63 proÄ, teorie) -ÄisltĂ© 3-(3â-ohlor-5â-trifluorme thylpyridyl-2â-oxy)benzoovĂ© kyseliny -o teplotÄ -tĂĄnĂ 141 aĆŸ 145 °C.
PĆĂklad 2
2-nitro-5- (3â,5â-dichlorpyri-dyl-2â-oxy) -2-benzonitril
K -suspenzi 2,4 g hydridu sodnĂ©ho (0,1 mol) ve 30 - ml N-methylpyrrolidonu se pĆi,kape 16,4 g 3-kyan-4-nitrofeno.lu (0,1 -mol) rozpuĆĄtÄnĂ©ho v 50 ml N-methylpyrrolidonu. ,Po ukonÄenĂ vĂœvinu vodĂku -se pĆidĂĄ 16,6 -g ,2-Ăluor-3,5-dichlorpyridinu (0,1 mol). ReakÄnĂ -smÄs se mĂchĂĄ 15 hodin pĆi teplotÄ - 110 aĆŸ 115 °C -a potom se vylije na ledovou vodu. VodnĂĄ smÄs <se etxrahuje chloroformem, Chloroform se vysuĆĄĂ -sĂranem sodnĂœm a odpaĆĂ se. Zbytek se ÄistĂ na sloupci -silikagelu za pouĆŸitĂ -smÄsi - ethylacetĂĄtu a -hexanu. ZĂskĂĄ se 6,2 -g (30 % teorie) titulnĂ - -slouÄeniny -o teplotÄ tĂĄnĂ 138 - aĆŸ 140 °C.
PĆĂklad 3
Methylester 2-nitro-5-( 3â,5â-dichlorpyridyl-2â-oxy) -benzoovĂ© kyseliny
Cl cooch3 Cl~(^0-<\~y~N0z
6,6 g 2-nitro-5-(3â;5â-dichlorpyridyl-2â-oxy)b&iTzoOvĂ© -kyseliny, -vyrobenĂ© analogicky podle pĆĂkladu 1, -se -smĂsĂ -s 10 -ml thionylchloridu -a smÄs se mĂchĂĄ po dobu 15 hodin pĆi teplotÄ 60 °C. NadbyteÄnĂœ thionylchlorid -se odpaĆĂ. Zbytek -se rozpustĂ v 50 ml toluenu. K tomuto roztoku se pĆidĂĄ 1 g methanolu a 2,1 g triethylaminu. Po 1 hodinÄ se -sĆŻl odfiltruje. - FiltrĂĄt -se odpaĆĂ azbytek krystaluje pĆi pĆidĂĄnĂ ethylacetĂĄtu a hexanu. ZĂskajĂ -se 4 g (62 % teorie) titulnĂ -slouÄeniny o teplotÄ tĂĄnĂ 81 aĆŸ 82 °C.
AnalogickĂœm zpĆŻsobem jako je popsĂĄn- ve shora uvedenĂœch pĆĂkladech se zĂskajĂ nĂĄsledujĂcĂ slouÄeniny: .
Ń ĐĄĐĐ
| pĆĂklad ÄĂslo | X | Y | ĐČ |
| 1 | Cl | Cl | OH |
| 2 | Cl | Cl | OCH3 |
| 3 | Cl | Cl | . OC2H5 |
| 4 | Cl | Cl | ĐĐĄĐĐ7Đ |
| 5 | Cl | Cl | OC3H7ĂSO |
| 6 | Cl | Cl | OÄ4H9n |
| 7 | Cl | Cl | OC4Hgse'k |
| 8 | Cl | Cl | OC4H9ĂSO |
| 9 | Cl | Cl | OC4Hgterc |
| 10 | Cl | Cl | 0C5HHĂSÄ CH3 |
| 11 | Cl | Cl | OCHC3H7 |
| 12 | Cl | Cl | OCH(C2H5)2 |
| 13 | Cl | Cl | OCH2CH2OCH3 |
| 14 | Cl | Cl | OCH2CH2OC2H5 |
| 15 | Cl | Cl | OCH2CH2OC4H9 0 z\ |
| 16 | Cl | Cl | OCH2CHâCH2 |
| 17 | Cl | Cl | OCH2CH2N(CH3)2 |
| 18 | Cl | Cl | OCH^CH^N^y CH3 |
| 19 | Cl | Cl | OCHCOOCH3 |
| 20 | Cl | Cl | O(CH2)3N(CH3)2 |
| 21 | Cl | Cl | OCH2CH=CH2 |
| 22 | Cl | Cl | OCH2CH=CHCH3 |
| 23 | Cl | Cl | OCH2C^CH |
| 124 | Cl | Cl | OCH2C=CâCH3 CH3 |
| 25 | Cl | Cl | 1 ĐĐĄâCH=CH2 C»CH |
| 26 | Cl | Cl | i Ń Ń=ŃĐœ |
| 27 | Cl | Cl | och2cn |
| 28 | Cl | Cl | OCH2CH2C1 |
| 29 | Cl | Cl | IOCH2CH2Br |
| 30 | Cl | Cl | nh2 |
| 31 | Cl | Cl | NHCH3 |
| 32 | Cl | Cl | nhc2h5 |
| 33 | Cl | Cl | NHC3H7(Ăso) |
| 34 | Cl | Cl | nhch2ch=ch2 |
| 35 | Cl | Cl | nhch2c=ch |
| 36 | Cl | Cl | . NHC4H9(sek) |
| 37 | Cl | Cl | NHCH(C2H5)2 |
| 38 | Cl | Cl | nhch2cooch3 |
| 39 | Cl | Cl | . N(CH3)2 |
| 40 | Cl | Cl | IN(C2H5)2 |
fyzikĂĄlnĂ data
t. t. 166-169°
1.1 81â82° nD 25 1,5815 nD 30 1,5840 nD 25 1,5680 nD 27 1,5675 nD 27 1,5677 nÄ 27 1,5620 nD 30 1,5817 nD 27 1,5605 nD 25 1,5877
t. t. 81-82° nD 27 1,5890
t. t. 179â180°
t. Ć€. 119â120°
| pĆĂklad ÄĂslo | X | Y | ĐČ | fyzikĂĄlnĂ data |
| 41 | Cl | Cl | Î | |
| 42 | Cl | Cl | ||
| 43 | Cl | H | OH | t. t. 166â169° |
| 44 | Cl | H | OCH3 | |
| 45 | Cl | H | oc2H5 | |
| 46 | Cl | H | N(CH3)2 | |
| 47 | Cl | H | NHCH2COOC2H5 | |
| 48 | Cl | Cl | NH-O | |
| 49 | Cl | H | ||
| 50 | Cl | Cl | SCH3 | nD 27 1,6200 |
| 51 | Cl | Cl | SC2H5 | |
| 52 | Cl | Cl | SC4H9(.iso) | nD 27 1,5965 |
| 53 | Cl | Cl | SCH2CH=CH2 | nD 27 1,6060 |
| 54 | Cl | Cl | SCH2COOCH3 | |
| 55 | Cl | Cl | ISCH2C=CH | |
| 56 | Cl | Cl | SCH2C^CHCH3 | |
| 57 | Cl | Br | OH | |
| 58 | Cl | Br | OCH3 | |
| 59 | Cl | Br | OC2H5 | |
| 60 | Cl | Br | 0C5H9(ĂS0) | |
| 61 | Cl. | Br | OC4H9(sek) | |
| 62 | Cl | Br | SC3H7(n) | |
| 63 | Cl | Br | SC4H9(n) | |
| 64 | Cl | Br | SCH2CH=CH2 | |
| 65 | Cl | Br | OCH(CH2)4 | |
| 66 | Cl | Br | OCH2CH(CH2)5 | |
| 67 | Cl | Br | NHC2H5 | |
| 68 | Cl | Br | NHC3H7(Ăso) | |
| 69 | Cl | Br | nhc8h17 | |
| 70 | Cl | Br | N(CH2CH=CH2)2 | |
| 71 | Br | Cl | OH | |
| 72 | Br | Cl | OCH3 | |
| 73 | Br | Cl | OC2H5 | |
| 74 | Br | Cl | OC3H7(iso) | |
| 75 | Br | Cl | OC4H9(lsek) | |
| 76 | Br | Cl | OC4Hg(iso) | |
| 77 | Br | Cl | OC4H9(terc) | |
| 78 | Br | Cl | OCH(CH2CH3)2 | |
| 79 | Br | Cl | OCHC3H7 1 CH3 | |
| 80 | Br | Cl | SCH3 | |
| 81 | Br | Cl | SC3H7 | |
| 82 | CF3 | Cl | OH | (t. t. 114â117° |
| 83 | CF3 | Cl | OCH3 | 11^1,5357 , |
| 84 | CF3 | Cl | OC2H5 | |
| 85 | CF3 | Cl | OC3H7(n) | |
| 86 | CF3 | Cl | OC3H7 (is 0 ] | nn30 1,5278 |
| 87 | CF3 | Cl | OC4Hg(n) | |
| 88 | CF3 | Cl | OC4H9(iso) | ĐĐČ20 1,5225 |
| 89 | CF3 | Cl | OC4H9(sek) | ĐĐČ30 1,5265 |
| 90 | CF3 | Cl | O(CH2)4C1 | ĐĐČ30 1,5350 |
| 91 | CF3 | Cl | OCsH^Ăn) | |
| 92 | CF3 | Cl | OCHC3H7 | ĐĐŸÂ» 1,5174 |
ŃĐœ3
| pĆĂklad ÄĂslo | X | Y | B | fyzikĂĄlnĂ 'data |
| 93 | CF3 | .....Cl | och(c2h5)2 | |
| 94 | CF3 | Cl | OCH2CH2CH(CH3)2 | |
| 95 | CF3 | Cl | ĐŸĐ°ĐŽŃĐĄĐż) | |
| 96 | CF3 | Cl | OC7Hl5(n) | |
| 97 | CF3 | Cl | OCHCsHu(.n) | |
| 1 CHg | ||||
| 98 | CF3 | Cl | OC8H17(in) | no30 1,5125 |
| 99 | CF3 | Cl | OCH2CH2C1 | nD30 1,5485 |
| 100 | CF3 | Cl | OCH2CH2Br | |
| 101 | CF3 | Cl | och2ch2f | nD30 1,5365 |
| 102 | CF3 | Cl | OCH2CH2OCH3 | |
| 103 | CF3 | Cl | OCH2CH2OC4H9 | |
| 104 | CF, | Cl | OCH2CH2OC2H5 | |
| 105 | CF3 | Cl | OCH2CN CH3 1 * | t. t. 100â102° |
| 106 | CF3 | Cl | OCHCOOCH2CH3. | nD30 1,52 13 |
| 107 | CF3 | Cl | OCH2CH=-CH2 | nD 30 1,5411 |
| 108 | CF3 | Cl | OCH2CH=CHCH3 | |
| 109 | CF3 | cl | OCH2C=CH2 | |
| CHg | ||||
| 110 | CF3 | Cl | ochc-ch | t. 't. 94â96° |
| 111 | CF3 | Cl | OCHâC-CH | | |
| CHg | ||||
| 112 | CF3 | Cl | O(CH3)2C^CH | |
| 113 | CF3 | Cl | CaC/7 | |
| 0 | ||||
| z\ | ||||
| 114 â | CF3 | Cl | OCH2CHâCH2 | |
| CH3 | ||||
| '-âÎ | / | |||
| 115 | CF3 | Cl | ON==C | t. t. 89â91° |
| \ | ||||
| CHg | ||||
| 116 | CF3 | Cl | ||
| 117 | CF3 | Cl | t. t. 92â94° | |
| 118 | CF3 | Cl | t. t. 79â81° | |
| 119 | CFg | Cl | OCH2CH2N(CH3)2 | аЎ» 1,5336 |
| 120 | CF3 | Cl | ||
| 121 | CF3 | Cl | OCH^ty-C H | |
| 122 | CFg | Cl | SCH3 | nO30 1,5695 |
| 123 | CF3 | Cl | SC2H5 | |
| 124 | CFg | Cl | SOAU) | |
| 125 | CFg | Cl | SC3H7(iso) | no30 1,5590 |
| 126 | CF3 | Cl | SC4H9(n) | |
| 127 | CF3 | Cl | SC4H9(iso) | |
| 128 | CF3 | Cl | SCSHi(n) |
2 O 8 0 O
| pĆĂklad ÄĂslo | X Y | B | fyzikĂĄlnĂ data | |
| 129 | CF3 | Cl | SCH2COOCH3 | no30 1,5650 |
| 130 | CF3 | Cl | SCH2CH==CH2 | noÂź 1,5725 |
| 131 | CF3 | Cl | SCH2C=CH | |
| 132 | CF3 | Cl | SCH2CH=CHCH3 | |
| 133 | CF3 | Cl | SCH2C=CH2 | |
| CH3 | ||||
| 134 | CF3 | Cl | S~O | |
| 135 | CF3 | Cl | SCH^-0 | <n'oÂź 1,5972 |
| 136 | CF3 | Cl | NHCH3 | t. 1139â142° |
| 137 | CF3 | Cl | NHC2H5 | |
| 138 | CF3 | Cl | NHCaH7(lso) | |
| 139 | CF3 | Cl | NHC4H9(h) | |
| 140 | CF3 | Cl | NHC4H9USO) | |
| 141 | CF3 | Cl | NHC5Hn(n) | |
| 142 | CF3 | Cl | NHCH(C2H5}2 | |
| 143 | CF3 | Cl | NĂ^HJn) | |
| 144 | CF3 | Cl | NHCH2CH2C1 | |
| 145 | CF3 | Cl | NHCH2CH2OH | |
| 146 | CF3 | Cl | NHCH2CH2OCH3 | |
| 147 | CF3 | Cl | NHCH2CH2OC4H9 | |
| 148 | CF3 | Cl | NHCH2COOC2H5 | |
| 149 | CF3 | Cl | nhch2c=ch | |
| 150 | CF3 | Cl | NHCH2CH=CH2 | |
| 151 | CF3 | Cl | NHC(CH3h=CH | |
| 152 | CF3 | Cl | NHC(CHaJjCN | |
| 153 | CF3 | Cl | HH-Q | |
| 154 | CF3 | Cl | wĂch- | |
| 155 | CF3 | Cl | N(CH3)2 | |
| 156 | CF3 | Cl | N(C2H512 | nD30 1,5352 |
| 157 | CF3 | Cl | N(CH2CH=CH2)2 | |
| 158 | CF3 | Cl | Î | |
| 159 | CF3 | Cl | >Tb | |
| \_v | ||||
| 160 | CF3 | Cl | nh2 | |
| 161 | CF3 | Cl | Î' © s Đș | |
| Î Âź | ||||
| 162 | CF3 | Cl | SNa | |
| ÎοΠo/· 1 | ||||
| 163 | CF3 | Cli | o NCityiso) | |
| 164 | CF3 | H | OH | . t. t. 139â144° |
| 165 | cf3 | H | OCH3 | |
| 166 | CF3 | H | OC2H5 | |
| 167 | CF3 | H | 0CsH7(n) | |
| 168 | CF3 | H | OC4H3(ieso) | |
| 169 | CF3 | H | OC,^Âź*) | |
| 170 | CF3 | H | OCHC3H7 |
ch3
| pĆĂklad ÄĂslo | X | Y | B |
| 171 | CF3 | H | SCH3 |
| 172 | CF3 | H | SC2H5 |
| 173 | CF3 | H | SC3H74ĂSO ) |
| 174 | CF3 | H | SC/.Hflso) |
| 175 | CF3 | H | SCsHh |
| 176 | CF3 | H | NH2 |
| 177 | CF3 | H | NHCH3 |
| 178 | CF3 | H | NHC2H5 |
| 179 | CF3 | H | NHCjHyflso] |
| 180 | CF3 | H | NHC4Hg(n) |
| 181 | CF3 | H | NHC3H13 |
| 182 | CF3 | H | NHCH2CH2C1 |
| 183 | CF3 | H | NHCH2CH2OCH3 |
| 184 | CF3 | H | nhch2c«ch |
| 185 | CF3 | H | nhch2c=ch |
| 186 | CF3 | H | NHCH2COOCH3 nhâĂ© SâCĂ |
| 187 | CF3 | H | CI |
| 188 | CF3 | H | N(CH3)2 |
| 189 | CF3 | H | N(CH2^H=CH2)2 |
| 190 | H | CF3 | OH |
| 191 | H | CF3 | OCH3 |
| 192 | H | CF3 | OC2H5 |
| 193 | H | CF3 | OC4H3(i6o) |
| 194 | H | CF3 | SCH3 |
| 195 | H | CF3 | SCH2CH=CH2 |
| 196 | H | CF3 | SC4H9(n) |
| 197 | H | CF3 | NHCH3 |
| 198 | H | CF3 | NHC2H5 |
| 199 | H | CF3 | NHCĂHgfso) |
| 200 | Cl | CF3 | OH |
| 201 | Cl | CF3 | OCH3 |
| 202 | Cl | CF3 | OC2H5 |
| 203 | Cl | CF3 | OCafyfiso) |
| 204 | Cl | CF3 | OCH2CH2OCH3 |
| 205 | Cl | CF3 | SCH3 |
| 206 | Cl | CF3 | NHCH3 |
| 207 | Cl | , CF3 | NHC2H5 |
| 208 | Cl | âą CFg | N(CH3)2 |
| 209 | Cl | CFg | N(CH2CHâCH2)2 |
| 210 | CC12F | Cl | OH |
| 211 | CC12F | Cl | OCH3 |
| 212 | CClaF | Cl | OC2H5 |
| 213 | CC12F | Cl | OC3H2(n) |
| 214 | CC12F | Cl | OC3H7(lso) |
| 215 | CC12.F | Cl | OC4H9(iso) |
| 216 | CC12F | Cl | OC4H9(sek) |
| 217 | cc12f | CI | OCH2CH2OCH3 |
| 218 | CC12F | Cl | SCH3 |
| 219 | CC12F | Cl | SC2H5 |
| 220 | CC12F | Cl | SCH2COOCH3 |
| 221 | CC12F | CI | NHCH3 |
| 222 | CC12F | Cl | N(CH3j2 |
| 223 | CC1F2 | Cl | OH |
| 224 | GC1F2 | ci | OCH3 |
| 225 | CC1F2 | Cl | OC2H5 |
| 226 | CC1F2 | Cl | OC3H7 |
| 227 | CC1F2 | Cl | OC4H9(iso) |
| 228 | CC1F2 | Cl | OC4H9(sek) |
| 229 | CCIFa | Cl | SCH3 |
| 230 | CC1F3 | Cl | NHCH3 |
fyzikĂĄlnĂ data
| pĆĂklad ÄĂslo | X | Y | ĐČ | fyzikĂĄlnĂ data |
| 231 | CF3 | Cl | NâOCH3 CH3 | |
| 232 | CF3 | Br | OCH3 | |
| 234 | CF3 | Br | oc2H5 | |
| 235 | CF3 | Br | OC4H9(iso] | |
| 236 | CF3 | Br | OC4H9(sek) | |
| 237 | CF3 | Br | SCH3 | |
| 238 | CF3 | Br | SC3H7(iso) | |
| 239 | CF3 | Br | NHCH2COOCH3 | |
| 240 | CF3 | Br | N(CH3)2 | |
| 241 | CF3 | Br | OCH2CH=CH2 | |
| 242 | Cl | Cl | NHC(CH3)2CN | !t. t. 160â162° |
| 243 | Cl | Cl | nhch2ch2och3 | t. t. 130â135° |
| 244 | Cl | Cl | t. t. 96â99° | |
| 245 | Cl | Cl | ĐĐĄĐ[ĐĄĐ3)ĐĄ5Đâ | nD 27 1,5600 |
| 246 | Cl | Cl | N(CH3)OCH3 | no34 1,6055 |
| 247 | Cl | Cl | OCH(CH3)COOCH2CH3 | |
| 248 | Cl | Cl | SC4H9(sek) | ĐĐŸ27 1,6000 |
| 249 | CF3 | Cl | SCH2COOCH2CH3 | |
| 250 | CF3 | Cl | N(CH3)OCH3 | nD3« 1,5438 |
| 251 | CF3 | Cl | NHSO2CH3 | t .t. 159 aĆŸ 162° |
| 252 | CF3 | Cl | 0©NaÂź | t. t. 200 aĆŸ 201° |
| 253 | CF3 | Cl X- | 0ÎÎÂź 7 A \\-0 -Ć„y-NOz | t. it. 152° (krystaly se roztÄkajĂ] |
N
| pĆĂklad ÄĂslo | X | Y | A | fyzikĂĄlnĂ data |
| 254 | Cl | Cl | CN | t ,t.138 aĆŸ 140° |
PĆĂklad 4
PĆĂprava nÄkterĂœch pĆĂmo upotĆebitelnĂœch aplikaÄnĂch forem a koncentrĂĄtĆŻ ĂșÄinnĂ© lĂĄtky:
Pasta:
Pro vĂœrobu 45% pasty se pouĆŸije nĂĄsledujĂcĂch lĂĄtek:
dĂlĆŻ 2-nitro-5-(3â,5â-dichlorpyridyl-2â-oxyjbenzoovĂ© kyseliny, dĂlĆŻ kĆemiÄitanĆŻ sodnohlinitĂ©ho, dĂlĆŻ cetylpolyglykoletheru s 8 mol â ethylenoxidu, dĂ'1 loleylpolyglykoletheru s 5 mol ethylenoxidu, dĂly vĆetenovĂ©ho oleje, dĂlĆŻ polyethylengly.kolu a dĂlĆŻ vody.
ĂÄinnĂĄ lĂĄtka se dĆŻkladnÄ smĂsĂ s pĆĂsadami a smÄs se rozemele v zaĆĂzenĂch vhodnĂœch pro tyto ĂșÄely. ZĂskĂĄ se pasta, ze kterĂ© se dajĂ ĆedÄnĂm vodou vyrĂĄbÄt suspenze kaĆŸdĂ© poĆŸadovanĂ© koncentrace.
EmulznĂ koncentrĂĄt:
Pro vĂœrobu 25% emulznĂho koncentrĂĄtu se vzĂĄjemnÄ smĂsĂ:
dĂlĆŻ methylesteru 2-nitro-5-(3â,5â-dichlorpyridyl-2â-oxy)lbenzoovĂ© kyseliny, dĂlĆŻ smÄsi nonylfenolpolyoxyethylenu a vĂĄpenatĂ© soli dodecylbenizensulfonovĂ© kyseliny, dĂlĆŻ cĂœklĂłhexanonu a dĂlĆŻ xylenu.
Tento koncentrĂĄt lze Ćedit vodou na emulze vhodnĂœch koncentracĂ, napĆĂklad 0,1 %. TakovĂ©to emulze jsou vhodnĂ© Đș potĂrĂĄnĂ plevelĆŻ v kulturnĂch plodinĂĄch.
SmĂĄÄitelnĂœ prĂĄĆĄek:
Pro vĂœrobu a) 70% a b) 10% smĂĄÄitelnĂ©ho prĂĄĆĄku se pouĆŸije nĂĄsledujĂcĂch sloĆŸek:
a) dĂlĆŻ isopropylesteru 2-nitro-5-(3â,5â-dichlorpyridyl-2â-oxy)benzoovĂ© kyseliny, dĂlĆŻ natriuĂmdibutylnaftylsulfonĂĄtu, dĂly kondenzaÄnĂho produktu naftalensulfonovĂœch kyselin, fenolsulfonovĂœcti kyselin a formaldehydu (3: :2:1), dĂlĆŻ kaolinu, dĂlĆŻ kĆĂdy (prov. Champagne);
b) dĂlĆŻ ĂșÄinnĂ© lĂĄtky, dĂly smÄsi sodnĂœch solĂ sulfatovanĂœch nasycenĂœch mastnĂœch alkoholĆŻ, dĂlĆŻ kondenzaÄnĂho produktu naftalensulfonovĂœch kyselin a formaldehydu, dĂlĆŻ kaolinu.
UvedenĂĄ ĂșÄinnĂĄ lĂĄtka se nanese na pĆĂsluĆĄnĂ© nosnĂ© lĂĄtky [kaolin a kĆĂdu) a potom se vĆĄe smĂsĂ a smÄs se rozemele spolu s ostatnĂmi sloĆŸkami. ZĂskĂĄ se smĂĄÄitelnĂœ prĂĄĆĄek s vĂœteÄnou smĂĄÄitelnostĂ a suspendovatelnostĂ. Z takovĂœchto smĂĄÄitelnĂœch prĂĄĆĄkĆŻ se mohou ĆedÄhĂm vodou zĂskat suspenze o obsahu 0,1 aĆŸ 8 % ĂșÄinnĂ© lĂĄtky, kterĂ© jsou vhodnĂ© Đș potĂrĂĄnĂ plevelĆŻ v kulturnĂch rostlinĂĄch.
PĆĂklad 5
HerbicidnĂ ĂșÄinek slouÄenin podle vynĂĄlezu byl zjiĆĄĆ„ovĂĄn nĂĄsledujĂcĂmi pokusy ve sklenĂku:
HerbicidnĂ ĂșÄinek pĆi preemergentnĂ aplikaci (inhlbice klĂÄenĂ):
Ve sklenĂku se do kvÄtinĂĄÄĆŻ o prĆŻmÄru asi 15 om zasejĂ semena rostlin, tak, ĂĄby se v jednom kvÄtinĂĄÄi mohlo vyvĂjet 12 aĆŸ 30 rostlinek. BezprostĆednÄ po zasetĂ pokusnĂœch rostlin se povrch pĆŻdy oĆĄetĆĂ vodnou disperzĂ ĂșÄinnĂœch lĂĄtek, zĂskanou z 25 % emulznĂho koncentrĂĄtu popĆĂpadÄ z 25 % smĂĄÄiteinĂ©ho prĂĄĆĄku Ăv pĆĂpadÄ slouÄenin, kterĂ© se v dĆŻsledku nedostateÄnĂ© rozpustnosti nemohou zpracovĂĄvat na emulznĂ koncentrĂĄt.
Bylo pouĆŸito 4 rĆŻznĂœch Ćad koncentracĂ odpovĂdajĂcĂch 4, 2, 1 a 0,5 kg ĂșÄinnĂ© lĂĄtky na 1 ha. KvÄtinĂĄÄe se udrĆŸujĂ ve sklenĂku pĆi teplotÄ 22 aĆŸ 25 °C a pĆi 50 aĆŸ 70% relativnĂ vlhkosti vzduchu a pokus se vyhodnotĂ po 3 tĂœdnech.
TestovanĂ© slouÄeniny vzorce I vykazujĂ pĆi tomto testu pĆi aplikovanĂœch mnoĆŸstvĂch 1 a 2 kg/ha prakticky pouĆŸitelnĂœ ĂșÄinek vĆŻÄi ĆĄirokolistĂœm plevelĆŻm, a takĂ© vĆŻÄi vÄtĆĄinÄ travnatĂœch plevelĆŻ, zatĂmco kulturnĂ rostliny, jako kukuĆice a z ÄĂĄsti takĂ© pĆĄenice, Äirok, rĂœĆŸe, sĂłja a bavlnĂk zĆŻstĂĄvajĂ nepoĆĄkozeny nebo jsou poĆĄkozovĂĄny jen nepodstatnÄ.
VĂœsledky se hodnotĂ podle nĂĄsledujĂcĂ stupnice:
= rostliny neklĂcĂ, nebo jsou ĂșplnÄ odumĆelĂ©
2â3 = velmi silnĂœ ĂșÄinek
4â6 = stĆednĂ ĂșÄinek
7â8 = nepatrnĂœ ĂșÄinek = ĆŸĂĄdnĂœ ĂșÄinek (jako neoĆĄetĆenĂĄ kontrola)
Jako srovnĂĄvacĂ lĂĄtky byly testovĂĄny: A = 2,4-dichlorfenyl-4â-nitrofenylether Đ = methylester ai-[4-[2,4-dichlorfenoxy)fenoxy ] propionovĂ© kyseliny.
VĂœsledky testu jsou shrnuty v nĂĄsledujĂcĂ talbulce:
Stellaria
T a b u 1 k a
PreemergentnĂ ĂșÄinek pouĆŸitĂ© mnoĆŸstvn 4 kg ĂșÄrnnĂ© lĂĄtky/'ha
| SlouÄenina Ä. | Avena | Setaria | SĂnapis |
| 1 | 6 | 2 | 2 |
| 2 | 6 | 1 | 4 |
| 5 | 6 | 2 | 9 |
| 7 | 8 | 2 | 9 |
| 8 | 8 | 4 | 7 |
| 10 | 9 | 5 | 7 |
| 11 | 9 | 4 | 9 |
| 15 | 7 | 2 | 4 |
| 17 | 9 | 5 | 7 |
| 19 | 8 | 2 | 2 |
| 22 | 5 | 2 | 6 |
| 23 | 6 | 2 | 4 |
| 27 | 5 | 2 | 6 |
| 30 | 9 | 4 | 5 |
| 32 | 4 | 2 | 3 |
| 43 | 8 | 7 | 7 |
| 51 | 7 | 2 | 5 |
| 52 | 7 | 5 | 9 |
| 54 | 6 | 4 | 7 |
| 82 | 5 | 1 | 3 |
| 83 | 7 | 1 | 3 |
| 86 | 5 | 1 | 6 |
| 88 | 9 | 2 | 8 |
| 89 | 9 | 2 | 8 |
| 90 | 6 | 2 | 5 |
| 92 | 9 | 2 | 9 |
| 98 | 6 | 2 | 3 |
| 99 | 3 | 1 | 1 |
| 102 | 3 | 1 | 2 |
| 105 | 3 | 2 | 2 |
| 106 | 2 | 1 | 1 |
| 107 | 3 | 1 | 2 |
| 110 | 3 | 2 | 3 |
| 115 | 2 | 1 | 1 |
| 117 | 5 | 2 | 4 |
| 118 | 8 | 8 | 7 |
| 119 | 2 | 1 | 1 |
| 122 | 7 | 1 | 2 |
| 125 | 8 | 2 | 8 |
| 129 | 4 | 2 | 5 |
| 130 | 8 | 2 | 6 |
| 135 | 8 | 2 | 9 |
| 136 | 5 | 1 | 1 |
| 156 | 9 | 2 | 3 |
| 164 | 6 | 2 | 4 |
| 242 | 9 | 9 | 8 |
| 243 | 3 | 2 | 2 |
| 244 | 9 | 4 | 8 |
| 245 | 9 | 2 | 6 |
| 246 | 7 | 1 | 3 |
| 248 | 7 | 6 | 9 |
| 250 | 5 | 2 | 3 |
| 251 | 6 | 1 | 1 |
| 254 | 9 | 9 | 9 |
| A | 3 | 1 | 8 |
| B | 6 | â3 | 4 |
^CDCDCnOO^CHCO^OO^CnCÄOOCDOOCDCOCDCD^lOOCDCDOOCDCD^l^CDCDOOCDCDCDM^aĂCD^OoaJOOOO^^OoOo^lCDOoOOCO^OOrfi.
HerbicidnĂ ĂșÄinek pĆi postemergentnĂ aplikaci (kontaktnĂ ĂșÄinek):
VÄtĆĄĂ poÄet plevelĆŻ <a kulturnĂch rostlin, a to jak jednodÄloĆŸnĂœch, tak i dvojdÄloĆŸnĂœch, ise po vzejitĂ (ve stadiu 4 aĆŸ 6 listĆŻ) postĆĂkĂĄ vodnou disperzĂ ĂșÄinnĂ© lĂĄtky v dĂĄvkĂĄch 0,5, 1, 2 a 4 kg/ha (aplikace na listy rostlin) a rostliny se udrĆŸujĂ pĆi teplotÄ 24 aĆŸ 26 °C a pĆi 45- aĆŸ 60% relativnĂ vlhkosti vzduchu. 3 tĂœdny po oĆĄetĆenĂ se pokus vyhodnotĂ.
TakĂ© pĆi tomto pokusu vykazujĂ slouÄeniny vzorce I vesmÄs upotĆebitelnĂœ ĂșÄinek proti ĆĄirokolistĂœm plevelĆŻm a proti vÄtĆĄinÄ travnatĂœch plevelĆŻ pĆi aplikovanĂ©m mnoĆŸstvĂ 1 kg ĂșÄinnĂ© lĂĄtky na 1 ha, pĆiÄemĆŸ kulturnĂ rostliny, jako kukuĆice, rĆŻznĂ© druhy obilovin jako jeÄmen, Äirok a rĂœĆŸe, jakoĆŸ i bavlnĂk a sĂłja zĆŻstĂĄvajĂ nepoĆĄkozeny nebo jsou poĆĄkozovĂĄny teprve za pouĆŸitĂ vÄtĆĄĂch aplikovanĂœch mnoĆŸstvĂ ĂșÄinnĂ© lĂĄtky.
HodnocenĂ testu a srovnĂĄvacĂ lĂĄtky jsou shodnĂ© jako pĆi testu, kde aplikace byla provedena preemergentnÄ.
VĂœsledky testu jsou shrnuty v nĂĄsledujĂcĂ tabulce:
Tabulka
PostemergentnĂ ĂșÄinek aplikovanĂ© mnoĆŸstvĂ: 4 kg ĂșÄinnĂ© lĂĄtky/ha
SlouÄe- Avena Setairia Lolium SolĂĄrnĂm Sinapis Stellaria Phaseolus nina Ä.
| 1 | 6 | 1 | 6 | 1 | 1 | 2 |
| 2 | 1 | 1 | 2 | 1 | 1 | 6 |
| 5 | 3 | 1 | 2 | 1 | 1 | 2 |
| 7 | 3 | 1 | 3 | 1 | 1 | 5 |
| 8 | 6 | 3 | 4 | 1 | 4 | 4 |
| 10 | 3 | 3 | 3 | 2 | 3 | 5 |
| 11 | 5 | 3 | 5 | 2 | 2 | 2 |
| 15 | 4 | 2 | 3 | 1 | 2 | 3 |
| 17 | 5 | 2 | 4 | 1 | 1 | 9 |
| 19 | 4 | 2 | 3 | 1 | 1 | 5 |
| 22 | 4 | 3 | 3 | 1 | 2 | 4 |
| 23 | 3 | 3 | 2 | 1 | 1 | 5 |
| 27 | 3 | 4 | 3 | 1 | 1 | 6 |
| 30 | 7 | 6 | 9 | 2 | 7 | 9 |
| 32 | 9 | 5 | 7 | 1 | 6 | 9 |
| 43 | 8 | 5 | 8 | 4 | 1 | 7 |
| 51 | 3 | 2 | 2 | 1 | 2 | 3 |
| 52 | 4 | 5 | 4 | 2 | 3 | 5 |
| 54 | 3 | 2 | 4 | 1 | 1 | 8 |
| 82 | 2 | 1 | 2 | 1 | 1 | 3 |
| 83 | 2 | 1 | 2 | 1 | 1 | 1 |
| 86 | 2 | 1 | 1 | 1 | 1 | 1 |
| 88 | 2 | 1 | 2 | 1 | 1 | 6 |
| 89 | 2 | 1 | 2 | 1 | 1 | 5 |
| 90 | 6 | 2 | 4 | 2 | 3 | 6 |
| 92 | 5 | 1 | 4 | >2 | 2 | 8 |
| 98 | 3 | 1 | 5 | 2 | 1 | 7 |
| 99 | 2 | 1 | 3 | 1 | 1 | 5 |
| 102 | 3 | 1 | 2 | 1 | 1 | 5 |
| 105 | 3 | 2 | 3 | 1 | 1 | 4 |
| 106 | 1 | 1 | 2 | 1 | 1 | 2 |
| 107 | 2 | 1 | 2 | 1 | 1 | 4 |
| 110 | 2 | 1 | 3 | 1 | 1 | 6 |
| 115 | 1 | 1 | 2 | 1 | 1 | 4 |
| 117 | 4 | 5 | 6 | 2 | 3 | 8 |
| 118 | 7 | 9 | 8 | 2 | 2 | 9 |
| 119 | 2 | 1 | 1 | 1 | 1 | 4 |
| 122 | 3 | 1 | 3 | 1 | 1 | 5 |
| 125 | 4 | 4 | 4 | 2 | 2 | 8 |
| 129 | 2 | 1 | 2 | 1 | 1 | 8 |
| 130 | 5 | 3 | 5 | 1 | 1 | 9 |
| 135 | 8 | 6 | 6 | 3 | 4 | 8 |
Claims (27)
1. HerbicidnĂ prostĆedek, vyznaÄujĂcĂ se tĂm, ĆŸe - jako, ĂșÄinnou sloĆŸku obsahuje alespoĆ jeden derivĂĄt 5-[pyridyl-2,-oxy)-2-nitrobenzoovĂ© kyseliny obecnĂ©ho vzorce I v nÄmĆŸ
X znamenĂĄ halogen nebo halogenmethylovou skupinu,
Y znamenĂĄ vodĂk, halogen nebo halogenmethylovou-, skupinu,
A znamenĂĄ kyanoskupinu, zbytek â COB nebo popĆĂpadÄ ' methylovou - skupinou jednou nebo nÄkolikrĂĄte -substituovanou 2-oxazolinovou skupinu,
B znamenĂĄ zbytek âORb âSR2, âNR3R4 nebo âON^CfRrJo,
R, znamenĂĄ vodĂk, kationt alkalickĂ©ho- kovu, alkylovou skupinu s 1 aĆŸ 8 atomy uhlĂku, kterĂĄ je popĆĂpadÄ substituovĂĄna halogenem, kyanoskupinou, -alkoxyskupinou s 1 aĆŸ 4 atomy uhlĂku, alkoxykarbonylovou skupinou s 1 aĆŸ 4 atomy uhlĂku v alkoxylovĂ© ÄĂĄsti nebo dialkylaminoskupinou s 1 aĆŸ 4 atomy uhlĂku v alkylech, dĂĄle znamenĂĄ alkenylovou skupinu , -se 3 aĆŸ 6 atomy uhlĂku, alkinylovou skupinu se 3 , aĆŸ 6 atomy uhlĂku, cykloalkylovou skupinu se 3 aĆŸ 6 atomy uhlĂku nebo fenylovĂœ nebo benzylovĂœ Zbytek, kterĂœ je popĆĂpadÄ substituovĂĄn halogenem,
R2 znamenĂĄ alkylovou , skupinu s 1 aĆŸ 6 atomy uhlĂku, kterĂĄ -je popĆĂpadÄ -substituovĂĄna alkoxykarbonylovou -kupinou s 1 aĆŸ '4 atomy uhlĂku v alkoxylovĂ© ÄĂĄsti, dĂĄle znamenĂĄ alkenylovou skupinu se 2 aĆŸ 4 atomy uhlĂku nebo benzylovou skupinu,
R3 a R4 znamenajĂ nezĂĄvisle na sobÄ vodĂk nebo- alkylovou -skupinu -s 1 aĆŸ 4- atomy uhlĂku, kterĂĄ je popĆĂpadÄ substituovĂĄna kyanoskupinou -nebo alkoxyskupinou -s 1 aĆŸ 4 -atomy uhlĂku, nebo -jeden ze subistituentĆŻ
R3 -a - R4 znamenĂĄ takĂ© -alkoxyskupinu -s 1 aĆŸ 4 atomy uhlĂku nebo alkylsulfonylovou skupinu -s 1 aĆŸ 4 atomy uhlĂku- a
R5 znamenĂĄ alkylovou . -skupinu s 1 aĆŸ 4 atomy uhlĂku.
2. ProttĆedek - oddl e -bodu 1 - vyznaÄujĂc Ă se tĂm, ĆŸe jako ĂșÄinnou -sloĆŸku obsahuje alespoĆ jeden derivĂĄt 5-(pyridyl-2,-oxy]-2-nitrαbenybovĂ© kyseliny obecnĂ©ho vzorce I, v nÄmĆŸ X, Y a A majĂ vĂœznam uvedenĂœ v bodÄ 1,
B znamenĂĄ ĆŸbytek âORb âSR2 ' -nebo -NR3R4,
Rt znamenĂĄ vodĂk, kationt alkalickĂ©ho kovu, alkylovou -skupinu s 1 aĆŸ 8 atomy uhlĂku, kterĂĄ je popĆĂpadÄ -substituovĂĄna halogenem, kyanbskduinbu, alkbxyskdpinod -s 1 aĆŸ 4 atomy uhlĂku, alkoxykarbonylovou skupinou s 1 aĆŸ 4 atomy uhlĂku v alkoxylovĂ© ÄĂĄsti nebo - dialkylaminbskdpinod s 1 aĆŸ 4 atomy uhlĂku v alkylech, dĂĄle znamenĂĄ alkenylovou -skupinu se 3 aĆŸ 6 atomy uhlĂku, alkinylovou skupinu se 3 aĆŸ 6 atomy uhlĂku, cykloalkylovou skupinu -se 3 aĆŸ 6 atomy uhlĂku nebo fenylovĂœ nebo benzylovĂœ zbytek, kterĂœ je popĆĂpadÄ -substituovĂĄn halogenem,
R2- znamenĂĄ alkylovou -skupinu -s 1 aĆŸ 6 atomy uhlĂku, kterĂĄ je popĆĂpadÄ substituovĂĄna alkbxykarbonylbvbu skupinou s 1 aĆŸ 4 atomy uhlĂku -v alkoxylovĂ© ÄĂĄsti, dĂĄle- znamenĂĄ alkenylovou -skupinu se 3 aĆŸ 4 atomy uhlĂku nebo benzylovou skupinu,
R3 -a R4 znamenajĂ nezĂĄvisle na -sobÄ -vo220800 dĂk nebo alkylovou skupinu s 1 aĆŸ 4 atomy uhlĂku, kterĂĄ je popĆĂpadÄ substituovĂĄna alkoxyskupinou s 1 aĆŸ 4 atomy uhlĂku nebo jeden ze sĂșbstituentĆŻ,
R3 a R4 znamenĂĄ takĂ© alkoxyskupinu s 1 aĆŸ 4 atomy uhlĂku.
3. ProstĆedek podle bodu 2, vyznaÄujĂcĂ se tĂm, ĆŸe j'ako ĂșÄinnou sloĆŸku obsahuje alespoĆ jeden derivĂĄt 5-(pyridyl-2â-oxy)-2-nitrobenzoovĂ© kyseliny obecnĂ©ho vzorce I, v nÄmĆŸ A znamenĂĄ skupinu âCOB, zatĂmco· X, Y a B majĂ vĂœznam uvedenĂœ v bodÄ 2.
4. ProstĆedek podle bodu 2, vyznaÄujĂcĂ se tĂm, ĆŸe jato ĂșÄinnou sloĆŸku obsahuje alespoĆ jeden derivĂĄt 5-(pyridyl-2â-oxy)-2-nitrobenzoovĂ© kyseliny obecnĂ©ho vzorce la
B mĂĄ vĂœznam uvedenĂœ v bodÄ 2.
5. ProstĆedek podle bodu 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje alespoĆ jeden derivĂĄt 5-(pyridyl-2â-oxy)-2-nitrobenzoovĂ© kyseliny obecnĂ©ho vzorce Ib
B · znamenĂĄ skupinu â ORt, âSR2 nebo âNR3R4, pĆiÄemĆŸ
Rj znamenĂĄ alkylovou skupinu s 1 aĆŸ 8 atomy uhlĂku, alkenylovou skupinu se 3 aĆŸ 6 atomy uhlĂku, alkinylovou skupinu se 3 aĆŸ 6 atomy uhlĂku, cykloalkylovou skupinu se 3 aĆŸ 6 atomy uhlĂku nebo popĆĂpadÄ halogenem substituovanou fenylovou skupinu a
R2, R3 a R4 majĂ vĂœznamy uvedenĂ© v bodÄ' 2.
6. ProstĆedek podle bodu 2, . vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje alespoĆ jeden derivĂĄt 5-(pyridyl-2â-oxy)-2-nitrolbenzoovĂ© kyseliny obecnĂ©ho vzorce Ic
COB (le) v nÄmĆŸ
B mĂĄ vĂœznam uvedenĂœ v bodÄ 2.
7. ProstĆedek podle bodu 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje alespoĆ jednu slouÄeninu obecnĂ©ho vzorce I, v nÄmĆŸ X nebo· Y znamenĂĄ chlor a druhĂœ z nich znamenĂĄ brom a A mĂĄ vĂœznam uvedenĂœ v bodÄ 2.
8. ProstĆedek podle bodu 2, vyznaÄujĂcĂ se tĂm, ĆŸe , Jako ĂșÄinnou sloĆŸku obsahuje alespoĆ jednu slouÄeninu obecnĂ©ho vzorce ÎȘ, v nÄmĆŸ X znamenĂĄ chlor, Y znamenĂĄ vodĂk a A mĂĄ vĂœznam uvedenĂœ v bodÄ 2.
9. ProstĆedek podle bodu 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje alespoĆ jednu slouÄeninu obecnĂ©ho vzorce I, v nÄmĆŸ X znamenĂĄ trifluormethylovou skupinu, Y znamenĂĄ brom a A mĂĄ vĂœznam uvedenĂœ v bodÄ 2.
10. ProstĆedek podle bodu 1 nebo· 2, vyznaÄujĂcĂ se tĂm, ĆŸe Jako ĂșÄinnou sloĆŸku obsahuje 5- (3â-chlor-5â-trif luormethylpyridyl-2â-oxy) -2-nitr obenzoovou kyselinu.
11. ProstĆedek ,podle bodu 1 nebo 2, vyznaÄujĂcĂ se, tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje nitril 5-(3â-chlor-5â-trifluormethylpyridyl-2â-oxy) -2-ni'trobenzoovĂ© kyseliny.
12. ProstĆedek podle bodu 1 nebo· 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje allylester 5-(3â-chlor-5*-trifluormethylpyridyl-2â-oxy )-2-<nitrobenzoovĂ© kyseliny.
13. ProstĆedek podle bodu 1 nebo· 2, · vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje isopropylester 5-(3â-chlor-5â-trifluormeĆ„hylpyridyl-2â-oxy)-2-nitrobenzoovĂ© kyseliny.
14. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje (ethoxykarbonyleth-r^yljester 5-[3â-chlor-5*-trifluormethyipyridyl-2â-oxyj-2-nitrobenzooivĂ© kyseliny.
15. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje (methoxy karbony Đ«^ĐŹŃĐĐ«ĐŸ) · ester 5- (3â-chlor-5â-trif luormethylpyridyl-2â-oxy) -2-nitirobenzoovĂ© kyseliny.
16. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje methylester 5-(3â,5â-dichlorpyridyl-2â-oxy) -2-nitrobenzoovĂ© kyseliny.
17. ProstĆedek · podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje amid 5-(3â,5â-dichlorpyridyl-2â-oxyj-2-ni-trobenzoovĂ© kyseliny.
18. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje 5- (5â-chlio^rpyrl·dyl-2â-oxy} -2-mirobenzoovou kyselinu.
19. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako· ĂșÄinnou , sloĆŸku obsahuje (2â-dimethyllaminothyl) ester 5-(3â-chlor-5â-trif luormethylpyridyl-2â-oxy) -2-nitrobenzoovĂ© kyseliny.
20. ProstĆedek podle bodu 1 nebo 2, vy220800
X a Y majĂ vĂœznam uvedenĂœ pod vzorcem
I v bodÄ 1, s derivĂĄtem 3-hydroxybenzoovĂ© kyseliny obecnĂ©ho vzorce IV znaiÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje propinylester 5-(3â-chlor-5â-trifluormethylpyridyl-2â-oxy) -2-nitrobenzoovĂ© kyseliny.
21. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje allylester 5-(3â-chlor-5â-trifluor.methylpyridyl-2â-oxy )-2-nitrobenzoovĂ© kyseliny.
22. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje (2â-,methoxyethyl)ester 5-(3â-chlor-5â-tirif luormethylpyridyl-2â-oxy) -2-nitrobenzoovĂ© kyseliny.
23. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou lĂĄtku obsahuje (2â-chlorethyl) ester 5-(3â-chlor-5â-trif luormethylpyridyl-2â-oxy) -2-nitr obenzoovĂ© kyseliny.
24. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou lĂĄtku obsahuje methylester 5-(3â-chlar-5â-trifluormethylpyridyl-2â-oxy) -2-nitrothiobenzoovĂ© kyseliny.
25. ProstĆedek podle bodu 1 nebo 2, vyznaÄujĂcĂ se tĂm, ĆŸe jako ĂșÄinnou sloĆŸku obsahuje (4â-bromfenyl) ester 5-(3â-chlor-5â-trif'luormethylpyridyl-2â-oxy) -2-nitrobenzoovĂ© kyseliny.
26. ZpĆŻsob vĂœroby ĂșÄinnĂ© sloĆŸky podle bodu 1, obecnĂ©ho vzorce I, vyznaÄujĂcĂ se tĂm, ĆŸe se v aprotickĂ©m rozpouĆĄtÄdle, v pĆĂtomnosti bĂĄze v mnoĆŸstvĂ vĂĄzajĂcĂm kyselinu, nechĂĄ reagovat 2-hialogenpyridin obecnĂ©ho vzorce II v nÄmĆŸ
Hal znamenĂĄ atom halogenu a v nÄmĆŸ
A mĂĄ vĂœznam uvedenĂœ v bodÄ 1, pod Vzorcem I, a zĂskanĂœ derivĂĄt 5-(pyridyl-2â-oxyjbenzoovĂ© kyseliny obecnĂ©ho vzorce V v nÄmĆŸ
Đ, X a Y majĂ vĂœznam uvedenĂœ pod vzorcem I v bodÄ 1, se nitruje nitraÄnĂ smÄsĂ.
27. ZpĆŻsob vĂœroby ĂșÄinnĂ© sloĆŸky podle bodu 2, obecnĂ©ho vzorce I, vyznaÄujĂcĂ se tĂm, ĆŸe se v aprotickĂ©m rozpouĆĄtÄdle, v pĆĂtomnosti bĂĄze v mnoĆŸstvĂ vĂĄzajĂcĂm kyselinu, nechĂĄ reagovat 2-halogenpyridin obecnĂ©ho vzorce II, v nÄmĆŸ Hal, X a Y majĂ vĂœznam uvedenĂœ v bodÄ 26, s derivĂĄtem 3-hydroxybenzoovĂ© kyseliny obecnĂ©ho vzorce IV, v nÄmĆŸ A mĂĄ vĂœznam uvedenĂœ v bodÄ 2, a zĂskanĂœ derivĂĄt 5-(pyridyl-2â-oxy)benzoovĂ© kyseliny obecnĂ©ho vzorce V, v nÄmĆŸ Đ, X a Y majĂ vĂœznam uvedenĂœ v bodÄ 2, se nitruje nitraÄnĂ smÄsĂ.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH743079 | 1979-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS220800B2 true CS220800B2 (en) | 1983-04-29 |
Family
ID=4325003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS805584A CS220800B2 (en) | 1979-08-14 | 1980-08-13 | Herbicide means and method of making the active substances |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US4326880A (cs) |
| EP (1) | EP0024259B1 (cs) |
| JP (1) | JPS5630962A (cs) |
| AR (1) | AR230626A1 (cs) |
| BR (1) | BR8005103A (cs) |
| CA (1) | CA1202033A (cs) |
| CS (1) | CS220800B2 (cs) |
| DD (1) | DD153993A3 (cs) |
| DE (1) | DE3070921D1 (cs) |
| DK (1) | DK349480A (cs) |
| HU (1) | HU187308B (cs) |
| IL (1) | IL60825A (cs) |
| PH (1) | PH15900A (cs) |
| PL (1) | PL130385B1 (cs) |
| PT (1) | PT71699B (cs) |
| ZA (1) | ZA804964B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4371736A (en) * | 1981-03-27 | 1983-02-01 | E. I. Du Pont De Nemours And Company | Herbicidal pyridinyloxy(pyrimidinyloxy)benzenes |
| US4451284A (en) * | 1981-07-28 | 1984-05-29 | Ciba-Geigy Corporation | Derivatives of 2-nitro-4- or -5-pyridyloxyphenylphosphonic acid, the preparation thereof, the use thereof as herbicides and/or plant growth regulators |
| US4480102A (en) * | 1982-07-23 | 1984-10-30 | The Dow Chemical Company | 2,3-Difluoro-5-(trifluoromethyl)pyridine and methods of making and using the same |
| GB8327658D0 (en) * | 1983-10-14 | 1983-11-16 | Fbc Ltd | Herbicides |
| DE3402982A1 (de) * | 1984-01-28 | 1985-08-01 | Bayer Ag, 5090 Leverkusen | Phenoxypropionyloxyalkanphosphonsaeureester |
| US4539039A (en) * | 1984-04-26 | 1985-09-03 | The Dow Chemical Company | Herbicidal (-3-fluoro-5-trifluoromethyl-pyridyl)oxy phenyloxime derivatives |
| JPH082883B2 (ja) * | 1986-06-06 | 1996-01-17 | ăŻăăąă€ććŠć·„æ„æ ȘćŒäŒç€Ÿ | ïŒâăăšăăă·ăăȘăăžăłèȘć°äœăăăłé€èć€ |
| US4964895A (en) * | 1987-06-08 | 1990-10-23 | Monsanto Company | Substituted 4-(4-nitrophenoxy) pyrazoles and their use as herbicides |
| CN1376145A (zh) * | 1998-11-30 | 2002-10-23 | çłćäș§äžæ ȘćŒäŒç€Ÿ | éŽçĄćșèŻé èĄçç©ćć ¶ć¶ć€æčæł |
| JP3502036B2 (ja) * | 2000-11-08 | 2004-03-02 | ă·ăŁăŒăæ ȘćŒäŒç€Ÿ | ćć°äœçŽ ćăźèŁœé æčæłăăăłćć°äœçŽ ć |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3784635A (en) * | 1969-04-25 | 1974-01-08 | Mobil Oil Corp | Substituted phenoxybenzoic acids and esters thereof |
| US3928416A (en) * | 1972-03-14 | 1975-12-23 | Rohm & Haas | Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers |
| CA1140563A (en) * | 1976-12-03 | 1983-02-01 | Wayne O. Johnson | Herbicidal esters of 4-trifluormethyl-3'- carboxy-4'-nitro diphenyl ethers |
| DE2861073D1 (en) * | 1977-06-29 | 1981-12-03 | Ciba Geigy Ag | Pyridyloxy-phenoxy-alkanoic acid derivatives , processes for their preparation and their use as herbicides or plant growth regulators |
| EP0003313B1 (de) * | 1978-01-27 | 1981-01-07 | Ciba-Geigy Ag | Neue Pyridyloxy-phenoxy-alpha-propionsÀure-aminoalkyl-ester mit herbizider Wirkung,ihre Herstellung, sie enthaltende Mittel und deren Verwendung |
| JPS54163582A (en) * | 1978-06-09 | 1979-12-26 | Ishihara Mining & Chemical Co | 22phenoxyy55 trifluoromethypiridine compound |
-
1980
- 1980-08-04 US US06/174,985 patent/US4326880A/en not_active Expired - Lifetime
- 1980-08-08 DE DE8080810248T patent/DE3070921D1/de not_active Expired
- 1980-08-08 EP EP80810248A patent/EP0024259B1/de not_active Expired
- 1980-08-12 PL PL1980226197A patent/PL130385B1/pl unknown
- 1980-08-12 AR AR282130A patent/AR230626A1/es active
- 1980-08-12 DD DD223272A patent/DD153993A3/xx unknown
- 1980-08-12 IL IL60825A patent/IL60825A/xx unknown
- 1980-08-12 CA CA000358100A patent/CA1202033A/en not_active Expired
- 1980-08-13 JP JP11157880A patent/JPS5630962A/ja active Pending
- 1980-08-13 HU HU802018A patent/HU187308B/hu unknown
- 1980-08-13 DK DK349480A patent/DK349480A/da not_active Application Discontinuation
- 1980-08-13 ZA ZA00804964A patent/ZA804964B/xx unknown
- 1980-08-13 CS CS805584A patent/CS220800B2/cs unknown
- 1980-08-13 PT PT71699A patent/PT71699B/pt unknown
- 1980-08-13 BR BR8005103A patent/BR8005103A/pt unknown
- 1980-08-14 PH PH24446A patent/PH15900A/en unknown
-
1982
- 1982-01-26 US US06/342,879 patent/US4420328A/en not_active Expired - Fee Related
-
1983
- 1983-09-09 US US06/530,802 patent/US4626275A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4326880A (en) | 1982-04-27 |
| HU187308B (en) | 1985-12-28 |
| PL130385B1 (en) | 1984-08-31 |
| AR230626A1 (es) | 1984-05-31 |
| US4420328A (en) | 1983-12-13 |
| CA1202033A (en) | 1986-03-18 |
| DK349480A (da) | 1981-02-15 |
| PT71699B (de) | 1981-06-17 |
| DE3070921D1 (en) | 1985-09-05 |
| DD153993A3 (de) | 1982-02-17 |
| EP0024259B1 (de) | 1985-07-31 |
| PH15900A (en) | 1983-04-15 |
| IL60825A (en) | 1984-05-31 |
| IL60825A0 (en) | 1980-10-26 |
| BR8005103A (pt) | 1981-02-24 |
| EP0024259A1 (de) | 1981-02-25 |
| PT71699A (de) | 1980-09-01 |
| ZA804964B (en) | 1981-08-26 |
| JPS5630962A (en) | 1981-03-28 |
| PL226197A1 (cs) | 1981-10-16 |
| US4626275A (en) | 1986-12-02 |
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