CH530421A - Verfahren zur Herstellung neuer Triazolyl-phosphorsäureester - Google Patents

Verfahren zur Herstellung neuer Triazolyl-phosphorsäureester

Info

Publication number: CH530421A
Authority: CH; Switzerland
Prior art keywords: formula; triazolyl; phosphoric acid; acid ester; hydroxy
Prior art date: 1970-10-22

Application number

CH1560970A

Other languages

German (de)

English (en)

Inventor

Dawes Dag

Beat Dr Boehner

Original Assignee

Agripat Sa

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.)

1970-10-22

Filing date

1970-10-22

Publication date

1972-11-15

1970-10-22 Application filed by Agripat Sa filed Critical Agripat Sa

1970-10-22 Priority to CH1560970A priority Critical patent/CH530421A/de

1970-10-22 Priority to CH708271A priority patent/CH533949A/de

1971-10-07 Priority to DE2150098A priority patent/DE2150098C3/de

1971-10-14 Priority to IL37934A priority patent/IL37934A/xx

1971-10-15 Priority to CA125,220A priority patent/CA956640A/en

1971-10-19 Priority to BG018809A priority patent/BG19087A3/bg

1971-10-19 Priority to US190674A priority patent/US3862170A/en

1971-10-19 Priority to AU34739/71A priority patent/AU465772B2/en

1971-10-20 Priority to PL1971151121A priority patent/PL76965B1/pl

1971-10-20 Priority to DD158429A priority patent/DD95375A5/xx

1971-10-21 Priority to NL7114515A priority patent/NL7114515A/xx

1971-10-21 Priority to IT30163/71A priority patent/IT954182B/it

1971-10-21 Priority to ES396231A priority patent/ES396231A1/es

1971-10-21 Priority to FR7137869A priority patent/FR2113066A5/fr

1971-10-21 Priority to BE774253A priority patent/BE774253A/xx

1971-10-21 Priority to AT909771A priority patent/AT309900B/de

1971-10-21 Priority to ZA717052A priority patent/ZA717052B/xx

1971-10-21 Priority to HUAI200A priority patent/HU163468B/hu

1971-10-21 Priority to GB4905471A priority patent/GB1377196A/en

1971-10-22 Priority to BR7083/71A priority patent/BR7107083D0/pt

1971-10-22 Priority to TR16864A priority patent/TR16864A/xx

1972-05-30 Priority to DD163292A priority patent/DD102068A5/xx

1972-11-15 Publication of CH530421A publication Critical patent/CH530421A/de

Links

-1 Triazolyl phosphates Chemical class 0.000 title claims description 18
229910019142 PO4 Inorganic materials 0.000 title 1
239000000575 pesticide Substances 0.000 title 1
235000021317 phosphate Nutrition 0.000 title 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 12
QEASJVYPHMYPJM-UHFFFAOYSA-N 1,2-dihydrotriazol-5-one Chemical compound OC1=CNN=N1 QEASJVYPHMYPJM-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
150000003015 phosphoric acid halides Chemical class 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 3
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 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
230000000895 acaricidal effect Effects 0.000 abstract description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 3
239000000706 filtrate Substances 0.000 abstract description 3
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract description 3
239000002917 insecticide Substances 0.000 abstract description 3
239000000741 silica gel Substances 0.000 abstract description 3
229910002027 silica gel Inorganic materials 0.000 abstract description 3
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract description 3
AKOJTNUBZFZDAV-UHFFFAOYSA-N (propan-2-ylamino)urea Chemical compound CC(C)NNC(N)=O AKOJTNUBZFZDAV-UHFFFAOYSA-N 0.000 abstract description 2
230000001069 nematicidal effect Effects 0.000 abstract description 2
239000000642 acaricide Substances 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
235000019439 ethyl acetate Nutrition 0.000 abstract 1
239000000417 fungicide Substances 0.000 abstract 1
239000005645 nematicide Substances 0.000 abstract 1
230000003032 phytopathogenic effect Effects 0.000 abstract 1
235000015320 potassium carbonate Nutrition 0.000 abstract 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 7
239000004480 active ingredient Substances 0.000 description 6
150000003580 thiophosphoric acid esters Chemical class 0.000 description 6
241000196324 Embryophyta Species 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
239000002689 soil Substances 0.000 description 4
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
XRQXVMGRJJXKDC-UHFFFAOYSA-N 2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CC(C)N1C=NC(O)=N1 XRQXVMGRJJXKDC-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000254173 Coleoptera Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
241001124076 Aphididae Species 0.000 description 2
241000257226 Muscidae Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000254109 Tenebrio molitor Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
LHCOZCRYTQNSBL-UHFFFAOYSA-N 2,2-bis(4-bromophenyl)-2-hydroxyacetic acid Chemical class C=1C=C(Br)C=CC=1C(O)(C(=O)O)C1=CC=C(Br)C=C1 LHCOZCRYTQNSBL-UHFFFAOYSA-N 0.000 description 1
IRJMHONLPHMVRM-UHFFFAOYSA-N 2-butan-2-yl-1H-1,2,4-triazol-5-one Chemical compound C(C)(CC)N1N=C(N=C1)O IRJMHONLPHMVRM-UHFFFAOYSA-N 0.000 description 1
241001143309 Acanthoscelides obtectus Species 0.000 description 1
241001533303 Acarinae Species 0.000 description 1
241000256118 Aedes aegypti Species 0.000 description 1
241000380490 Anguina Species 0.000 description 1
241001414900 Anopheles stephensi Species 0.000 description 1
241000294569 Aphelenchoides Species 0.000 description 1
241001425390 Aphis fabae Species 0.000 description 1
241000239223 Arachnida Species 0.000 description 1
241000238888 Argasidae Species 0.000 description 1
241000238421 Arthropoda Species 0.000 description 1
241000238662 Blatta orientalis Species 0.000 description 1
241000238660 Blattidae Species 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
241001388466 Bruchus rufimanus Species 0.000 description 1
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
IOJBNVBZZYSKNG-UHFFFAOYSA-N C[ClH]P(=S)(Cl)[ClH]C Chemical compound C[ClH]P(=S)(Cl)[ClH]C IOJBNVBZZYSKNG-UHFFFAOYSA-N 0.000 description 1
241001124134 Chrysomelidae Species 0.000 description 1
241001465977 Coccoidea Species 0.000 description 1
241000256057 Culex quinquefasciatus Species 0.000 description 1
241000256113 Culicidae Species 0.000 description 1
241000254171 Curculionidae Species 0.000 description 1
241001641896 Dermestes lardarius Species 0.000 description 1
241001513837 Dermestes maculatus Species 0.000 description 1
241000131287 Dermestidae Species 0.000 description 1
YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 1
241000255925 Diptera Species 0.000 description 1
241000399934 Ditylenchus Species 0.000 description 1
241000630736 Ephestia Species 0.000 description 1
241000122098 Ephestia kuehniella Species 0.000 description 1
241001232715 Granaria Species 0.000 description 1
241001148481 Helicotylenchus Species 0.000 description 1
241001480224 Heterodera Species 0.000 description 1
241000238889 Ixodidae Species 0.000 description 1
241000254022 Locusta migratoria Species 0.000 description 1
241001220360 Longidorus Species 0.000 description 1
241001143352 Meloidogyne Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000257159 Musca domestica Species 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
241000244206 Nematoda Species 0.000 description 1
241000256259 Noctuidae Species 0.000 description 1
241000238814 Orthoptera Species 0.000 description 1
241000131102 Oryzaephilus Species 0.000 description 1
241001148650 Paratylenchus Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
241000238661 Periplaneta Species 0.000 description 1
241000691880 Planococcus citri Species 0.000 description 1
241000193943 Pratylenchus Species 0.000 description 1
241001415279 Pseudococcidae Species 0.000 description 1
241000255893 Pyralidae Species 0.000 description 1
241001510071 Pyrrhocoridae Species 0.000 description 1
241000201377 Radopholus Species 0.000 description 1
241001540480 Rotylenchulus Species 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241001494115 Stomoxys calcitrans Species 0.000 description 1
241000254107 Tenebrionidae Species 0.000 description 1
241001220308 Trichodorus Species 0.000 description 1
241000855019 Tylenchorhynchus Species 0.000 description 1
241001267621 Tylenchulus semipenetrans Species 0.000 description 1
241000201423 Xiphinema Species 0.000 description 1
VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
244000309466 calf Species 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
229960002097 dibutylsuccinate Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
150000003008 phosphonic acid esters Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
229940070846 pyrethrins Drugs 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
150000003349 semicarbazides Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Dentistry (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1560970A 1970-10-22 1970-10-22 Verfahren zur Herstellung neuer Triazolyl-phosphorsäureester CH530421A (de)

Priority Applications (22)

Application Number	Priority Date	Filing Date	Title
CH1560970A CH530421A (de)	1970-10-22	1970-10-22	Verfahren zur Herstellung neuer Triazolyl-phosphorsäureester
CH708271A CH533949A (de)	1970-10-22	1970-10-22	Mittel zur Bekämpfung von Insekten, Spinnentieren und Nematoden
DE2150098A DE2150098C3 (de)	1970-10-22	1971-10-07	1,2,4-Triazolyl-3-phosphorsäureester, ihre Herstellung und diese enthaltende Schädlingsbekämpfungsmittel
IL37934A IL37934A (en)	1970-10-22	1971-10-14	Triazolyl phosphoric acid esters,their production and their use for pest control
CA125,220A CA956640A (en)	1970-10-22	1971-10-15	Esters
BG018809A BG19087A3 (bg)	1970-10-22	1971-10-19	Инсектицидно средство
US190674A US3862170A (en)	1970-10-22	1971-10-19	Triazolylphosphoric acid esters
AU34739/71A AU465772B2 (en)	1970-10-22	1971-10-19	Triazolylphosphoric acid esters
PL1971151121A PL76965B1 (bg)	1970-10-22	1971-10-20
DD158429A DD95375A5 (bg)	1970-10-22	1971-10-20
NL7114515A NL7114515A (bg)	1970-10-22	1971-10-21
IT30163/71A IT954182B (it)	1970-10-22	1971-10-21	Esteri loro preparazione e loro impiego in particolare per combat tere organismi nocivi
ES396231A ES396231A1 (es)	1970-10-22	1971-10-21	Procedimiento para la preparacion de nuevos esteres de aci-do triazolil-fosforico.
FR7137869A FR2113066A5 (bg)	1970-10-22	1971-10-21
BE774253A BE774253A (fr)	1970-10-22	1971-10-21	Esters phosphoriques et phosphorothioniques utilisables dans des produits pesticides
AT909771A AT309900B (de)	1970-10-22	1971-10-21	Schädlungsbekämpfungsmittel
ZA717052A ZA717052B (en)	1970-10-22	1971-10-21	New esters
HUAI200A HU163468B (bg)	1970-10-22	1971-10-21
GB4905471A GB1377196A (en)	1970-10-22	1971-10-21	Pesticidal triazolyl esters of phosphoric and thiophosphoric acids
BR7083/71A BR7107083D0 (pt)	1970-10-22	1971-10-22	Processo de preparacao de novos esteres e composicoes a base dos mesmos para combate de pragas
TR16864A TR16864A (tr)	1970-10-22	1971-10-22	Yeni triazolil fosforik asid esterleri ve bunlarin imaline mahsus usul
DD163292A DD102068A5 (bg)	1970-10-22	1972-05-30

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1560970A CH530421A (de)	1970-10-22	1970-10-22	Verfahren zur Herstellung neuer Triazolyl-phosphorsäureester

Publications (1)

Publication Number	Publication Date
CH530421A true CH530421A (de)	1972-11-15

Family

ID=4410508

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH708271A CH533949A (de)	1970-10-22	1970-10-22	Mittel zur Bekämpfung von Insekten, Spinnentieren und Nematoden
CH1560970A CH530421A (de)	1970-10-22	1970-10-22	Verfahren zur Herstellung neuer Triazolyl-phosphorsäureester

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CH708271A CH533949A (de)	1970-10-22	1970-10-22	Mittel zur Bekämpfung von Insekten, Spinnentieren und Nematoden

Country Status (6)

Country	Link
AU (1)	AU465772B2 (bg)
BG (1)	BG19087A3 (bg)
CH (2)	CH533949A (bg)
ES (1)	ES396231A1 (bg)
TR (1)	TR16864A (bg)
ZA (1)	ZA717052B (bg)

1970
- 1970-10-22 CH CH708271A patent/CH533949A/de not_active IP Right Cessation
- 1970-10-22 CH CH1560970A patent/CH530421A/de not_active IP Right Cessation
1971
- 1971-10-19 AU AU34739/71A patent/AU465772B2/en not_active Expired
- 1971-10-19 BG BG018809A patent/BG19087A3/bg unknown
- 1971-10-21 ZA ZA717052A patent/ZA717052B/xx unknown
- 1971-10-21 ES ES396231A patent/ES396231A1/es not_active Expired
- 1971-10-22 TR TR16864A patent/TR16864A/xx unknown

Also Published As

Publication number	Publication date
AU3473971A (en)	1973-05-03
BG19087A3 (bg)	1975-04-30
CH533949A (de)	1973-02-28
AU465772B2 (en)	1975-10-09
ES396231A1 (es)	1975-04-01
TR16864A (tr)	1973-07-01
ZA717052B (en)	1972-07-26

Legal Events

Date	Code	Title	Description
1981-06-30	PL	Patent ceased

Publication	Publication Date	Title
DE2219484A1 (de)	1973-10-31	0-pyrazolo(thiono)-phosphor(phosphon)saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE1950491A1 (de)	1971-04-22	Pyridazino-thiono-phosphor(phosphon)-saeureester,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide
CH530421A (de)	1972-11-15	Verfahren zur Herstellung neuer Triazolyl-phosphorsäureester
CA1081225A (en)	1980-07-08	(thiono) (thiol) pyridazinone-alkanephosphonic acid esters, and their use as insecticides and acaricides
US3987168A (en)	1976-10-19	O-Alkyl-O-[1-cyanoalkyl-5-substituted-mercapto-triazol(3)yl]-(thiono)-phosphoric(phosphonic) acid esters or ester-amides
DE1568639C3 (de)	1975-03-13	2,2-Dlchlor-vinyl-phosphorsäureesteramide, Verfahren zu deren Herstellung sowie insektizide und akarizide Mittel
DE2527676A1 (de)	1977-01-20	Triazolylmethylthiol(thiono)phosphor(phosphon)-saeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide
CH530424A (de)	1972-11-15	Verfahren zur Herstellung neuer Triazolyl-thiophosphonsäureester
DE2033947A1 (de)	1972-01-20	0 Pyrazolopynmidin (thiono) phosphor (phosphon)saureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insek tizide und Akanzide
DE2422548C2 (de)	1982-08-26	0-Triazolyl-(thiono)-phosphor(phosphon)-säureester und -esteramide, Verfahren zu ihrer Herstellung sowieihre Verwendung als Insektizide, Akarizide und Nematizide
DE2150098C3 (de)	1981-05-07	1,2,4-Triazolyl-3-phosphorsäureester, ihre Herstellung und diese enthaltende Schädlingsbekämpfungsmittel
US3734914A (en)	1973-05-22	2-oxodihydroquinolinethiono-phosphoric (phosphonic) acid esters
DE2143756A1 (de)	1973-03-08	0-phenyl-n-alkoxy-(thiono)-phosphor (phosphon)-saeureesteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2030509A1 (de)	1971-12-30	2-Cyanovinyl-(thio)-phosphor- bzw. -phosphonsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide
CH521379A (de)	1972-04-15	Verfahren zur Herstellung neuer Phosphorsäureester
DE2037853C3 (de)	1980-02-14	Pyrazole- (thiono)-phosphor(phosphon)saureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide
US4127653A (en)	1978-11-28	O-alkyl-6-chloro-benzisoxazol-(3)-yl-thionophosphoric (phosphonic) acid esters
DE1918753A1 (de)	1970-10-15	Neue Amidothionophosphorsaeurephenylester,Verfahren zu ihrer Herstellung sowie Verwendung als Insektizide und Akarizide
DE2350886A1 (de)	1974-04-18	Neue ester
DE2040410C3 (de)	1980-05-14	Benzisoxazolo(thiono)phosphor(phosphon)säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide
DE2242135A1 (de)	1974-03-07	(thiono)phosphor(phosphon)-saeureester-benzaldoxime, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
DE2031750A1 (de)	1972-01-05	Benzisoxazolo(thiono)phosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide
DE1930216A1 (de)	1970-12-17	Amidophosphoryl-salicylsaeureester,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide
DE2521400A1 (de)	1976-11-25	O-triazolyl(thiono)(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE1912972A1 (de)	1970-10-01	Phosphor-,Phosphon- bzw. Thionophosphor-(phosphon)-saeureester und Verfahren zu ihrer Herstellung