CS236651B2 - ínsekticidní, nematocidní a akaricidní prostředky a způsob výroby účinné složky - Google Patents

ínsekticidní, nematocidní a akaricidní prostředky a způsob výroby účinné složky Download PDF

Info

Publication number: CS236651B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; dimethyl; active ingredient; pyrimidinyl; sodium
Prior art date: 1971-03-04

Application number

CS138672A

Other languages

Czech (cs)

English (en)

Inventor

Karlheinz Nilzner

Fritz Reisser

Original Assignee

Karlheinz Nilzner

Fritz Reisser

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1971-03-04

Filing date

1972-03-02

Publication date

1985-05-15

1971-03-04 Priority claimed from CH319071A external-priority patent/CH549055A/de

1971-08-20 Priority claimed from CH1229871A external-priority patent/CH552018A/de

1972-03-02 Application filed by Karlheinz Nilzner, Fritz Reisser filed Critical Karlheinz Nilzner

1985-05-15 Publication of CS236651B2 publication Critical patent/CS236651B2/cs

Links

150000001875 compounds Chemical class 0.000 title claims description 40
230000000895 acaricidal effect Effects 0.000 title claims description 5
239000003795 chemical substances by application Substances 0.000 title description 4
239000000642 acaricide Substances 0.000 title 1
239000002917 insecticide Substances 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
239000005645 nematicide Substances 0.000 title 1
229910052760 oxygen Inorganic materials 0.000 claims description 64
-1 sodium or potassium Chemical group 0.000 claims description 33
239000000203 mixture Substances 0.000 claims description 28
239000004480 active ingredient Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 19
229910052717 sulfur Chemical group 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
239000000969 carrier Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
239000011734 sodium Substances 0.000 claims description 9
229910052708 sodium Inorganic materials 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
230000000749 insecticidal effect Effects 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
230000001069 nematicidal effect Effects 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
150000001768 cations Chemical group 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
FNEQSJOUOUGPBG-UHFFFAOYSA-N pyrimidin-2-yl dihydrogen phosphate Chemical compound OP(O)(=O)OC1=NC=CC=N1 FNEQSJOUOUGPBG-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 2
NKYPKIVMIGIWOB-UHFFFAOYSA-N [amino(methoxy)phosphinothioyl]oxymethane Chemical compound COP(N)(=S)OC NKYPKIVMIGIWOB-UHFFFAOYSA-N 0.000 claims 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 1
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
URAVJIKQIIUWQB-UHFFFAOYSA-N [O-]P(O)(O)=[S+]C1=NC=CC=N1 Chemical compound [O-]P(O)(O)=[S+]C1=NC=CC=N1 URAVJIKQIIUWQB-UHFFFAOYSA-N 0.000 claims 1
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
238000004458 analytical method Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
229910002091 carbon monoxide Inorganic materials 0.000 description 13
238000003756 stirring Methods 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 11
239000013543 active substance Substances 0.000 description 10
229910052698 phosphorus Inorganic materials 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000012230 colorless oil Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
240000001307 Myosotis scorpioides Species 0.000 description 4
241000244206 Nematoda Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241001124076 Aphididae Species 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000003269 fluorescent indicator Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
QOHAYIBKEPYUAR-UHFFFAOYSA-N 4-ethoxy-2-methyl-1h-pyrimidin-6-one Chemical compound CCOC1=CC(=O)NC(C)=N1 QOHAYIBKEPYUAR-UHFFFAOYSA-N 0.000 description 2
ZVPPHZDHBNMFNI-UHFFFAOYSA-N 4-methoxy-2-propan-2-yl-1h-pyrimidin-6-one Chemical compound COC1=CC(O)=NC(C(C)C)=N1 ZVPPHZDHBNMFNI-UHFFFAOYSA-N 0.000 description 2
FVAVDZBKIKAVAO-UHFFFAOYSA-N 4-methylsulfanyl-2-propan-2-yl-1H-pyrimidin-6-one Chemical compound C(C)(C)C1=NC(=CC(=N1)SC)O FVAVDZBKIKAVAO-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
241000239290 Araneae Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000244199 Panagrellus redivivus Species 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
241000253999 Phasmatodea Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000011097 chromatography purification Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
229920005610 lignin Chemical class 0.000 description 2
229910052625 palygorskite Inorganic materials 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
238000009736 wetting Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
MYBIHYFCOFCVIE-UHFFFAOYSA-N 2-ethyl-4-methoxy-1H-pyrimidin-6-one Chemical compound C(C)C1=NC(=CC(=N1)OC)O MYBIHYFCOFCVIE-UHFFFAOYSA-N 0.000 description 1
CHASCQSJHSQWNQ-UHFFFAOYSA-N 4-methoxy-2-methyl-1h-pyrimidin-6-one Chemical compound COC1=CC(=O)NC(C)=N1 CHASCQSJHSQWNQ-UHFFFAOYSA-N 0.000 description 1
XTRAWORUGOJWSH-UHFFFAOYSA-N 4-methoxy-2-methylpyrimidine Chemical compound COC1=CC=NC(C)=N1 XTRAWORUGOJWSH-UHFFFAOYSA-N 0.000 description 1
QNANRGHPXMUJQC-UHFFFAOYSA-N 6-chloro-2-methyl-1h-pyrimidin-4-one Chemical compound CC1=NC(=O)C=C(Cl)N1 QNANRGHPXMUJQC-UHFFFAOYSA-N 0.000 description 1
SYFHLNPUIWQMTB-UHFFFAOYSA-N 6-chloro-2-propan-2-yl-1h-pyrimidin-4-one Chemical compound CC(C)C1=NC(=O)C=C(Cl)N1 SYFHLNPUIWQMTB-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241001425390 Aphis fabae Species 0.000 description 1
LFUXUFXDVUTHLB-UHFFFAOYSA-N C(C)[ClH]P(=O)(Cl)[ClH]CC Chemical compound C(C)[ClH]P(=O)(Cl)[ClH]CC LFUXUFXDVUTHLB-UHFFFAOYSA-N 0.000 description 1
DGTHFTXUCGRIQO-UHFFFAOYSA-N C[ClH]P(=O)(Cl)[ClH]C Chemical compound C[ClH]P(=O)(Cl)[ClH]C DGTHFTXUCGRIQO-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-BKFZFHPZSA-N Calcium-45 Chemical group [45Ca] OYPRJOBELJOOCE-BKFZFHPZSA-N 0.000 description 1
241000254001 Carausius Species 0.000 description 1
241000254000 Carausius morosus Species 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
YCAGGFXSFQFVQL-UHFFFAOYSA-N Endothion Chemical compound COC1=COC(CSP(=O)(OC)OC)=CC1=O YCAGGFXSFQFVQL-UHFFFAOYSA-N 0.000 description 1
241000630736 Ephestia Species 0.000 description 1
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235000019738 Limestone Nutrition 0.000 description 1
240000001090 Papaver somniferum Species 0.000 description 1
235000008753 Papaver somniferum Nutrition 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
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XZRTXGYXEYGZJL-UHFFFAOYSA-N [amino(chloro)phosphoryl]oxymethane Chemical compound P(OC)(=O)(N)Cl XZRTXGYXEYGZJL-UHFFFAOYSA-N 0.000 description 1
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239000007900 aqueous suspension Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
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MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
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238000001704 evaporation Methods 0.000 description 1
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NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
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238000010438 heat treatment Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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239000004571 lime Substances 0.000 description 1
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239000000463 material Substances 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
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239000010446 mirabilite Substances 0.000 description 1
238000007479 molecular analysis Methods 0.000 description 1
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150000002790 naphthalenes Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
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239000003209 petroleum derivative Chemical class 0.000 description 1
PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
239000000049 pigment Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
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150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
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230000000087 stabilizing effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS138672A 1971-03-04 1972-03-02 ínsekticidní, nematocidní a akaricidní prostředky a způsob výroby účinné složky CS236651B2 (cs)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH319071A CH549055A (de)	1971-03-04	1971-03-04	Verfahren zur herstellung von phosphorsaeureestern.
CH1229871A CH552018A (de)	1971-08-20	1971-08-20	Verfahren zur herstellung von pyrimidinylphosphorsaeureamiden.
CH42972		1972-01-12

Publications (1)

Publication Number	Publication Date
CS236651B2 true CS236651B2 (cs)	1985-05-15

Family

ID=27172099

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS138672A CS236651B2 (cs)	1971-03-04	1972-03-02	ínsekticidní, nematocidní a akaricidní prostředky a způsob výroby účinné složky

Country Status (4)

Country	Link
AT (1)	AT328466B (de)
CS (1)	CS236651B2 (de)
ES (1)	ES400354A1 (de)
PL (1)	PL77515B1 (de)

1972
- 1972-03-02 ES ES400354A patent/ES400354A1/es not_active Expired
- 1972-03-02 CS CS138672A patent/CS236651B2/cs unknown
- 1972-03-02 PL PL15382672A patent/PL77515B1/pl unknown
- 1972-03-03 AT AT177672A patent/AT328466B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATA177672A (de)	1975-06-15
PL77515B1 (de)	1975-04-30
ES400354A1 (es)	1975-07-16
AT328466B (de)	1976-03-25

Publication	Publication Date	Title
CS235984B2 (en)	1985-05-15	Herbicide agent and method of its effective component production
PL173717B1 (pl)	1998-04-30	Sposób wytwarzania związków pirymidynowych
EP0224339A2 (de)	1987-06-03	Pyrimidinderivate, Verfahren zu deren Herstellung und diese enthaltende fungizide Zusammensetzung, für Landwirtschaft und Gartenbau
JPS61178986A (ja)	1986-08-11	１３β−ミルベマイシン誘導体，その製法，および有害生物防除剤組成物
NO834498L (no)	1977-06-30	Fremgangsmaate ved fremstilling av kjemiske forbindelser med herbicid aktivitet
CS204013B2 (en)	1981-03-31	Herbicide means
US3862188A (en)	1975-01-21	Pyrimidinyl phosphoric and thiophosphoric acid esters
CA1050033A (en)	1979-03-06	Triazolylorganophosphorus derivatives
US3402176A (en)	1968-09-17	O-pyrazolo-(1, 5-a)-pyrimidyl phosphorus-containing esters
US3794641A (en)	1974-02-26	Substituted phthalimido-1,3,5-triazines
US3629411A (en)	1971-12-21	Fungicidal compositions and methods of combating fungi using o-alkyl-s s-dialkyl dithiophosphates
GB2150565A (en)	1985-07-03	Pesticidal acylamino-s-triazines
US4045561A (en)	1977-08-30	Pesticidal pyrimidinyl phosphorus esters
US3454681A (en)	1969-07-08	Amido phosphorus-containing esters
US3594454A (en)	1971-07-20	2 - alkoxycarbonyl - 2 - chloro or lower alkyl vinyl diloweralkyl phosphates
US3808333A (en)	1974-04-30	O-(2-amino-4-methyl-pyrimidyl-6)-thiophosphoroamidate
US3928353A (en)	1975-12-23	Pyrimidyl phosphoro-and thiophosphoroamidates
SU581867A3 (ru)	1977-11-25	Способ получени эфиров о-пиразолопиримидин-(тионо)-фосфорной(фосфоновой)кислоты
US4115557A (en)	1978-09-19	Substituted pyridinyl O-alkyl phenyl/phosphonothioates and their use as pesticides
US2905700A (en)	1959-09-22	Phosphorus derivatives
GB2055103A (en)	1981-02-25	5-pyrimidinols and phosphorus esters thereof
IL33102A (en)	1970-03-22	Derivatives of thionophosphoric acid
US3847936A (en)	1974-11-12	O,o-dialkyl-o-(1,2-diazolidin-ones-5-yl-3)-thionophosphates
US3634435A (en)	1972-01-11	Certain s-(n-methylene-pyridone - (2)-o o-dilower-alkyl mono and dithio phosphates and derivatives
US3957801A (en)	1976-05-18	O,s-dialkyl esters of pyridylthio- and pyridyldithiophosphoric acid