CA1074326A - Esters - Google Patents
EstersInfo
- Publication number
- CA1074326A CA1074326A CA265,476A CA265476A CA1074326A CA 1074326 A CA1074326 A CA 1074326A CA 265476 A CA265476 A CA 265476A CA 1074326 A CA1074326 A CA 1074326A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- parts
- triazole
- pests
- active substance
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 12
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 241000238876 Acari Species 0.000 claims description 6
- 241000244206 Nematoda Species 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 230000003032 phytopathogenic effect Effects 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000005208 trialkylammonium group Chemical group 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 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 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000426497 Chilo suppressalis Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 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 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000534456 Arenaria <Aves> Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 240000002024 Gossypium herbaceum Species 0.000 description 2
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000949016 Rhipicephalus bursa Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 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 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 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 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
- FOIFBEVHAOADFO-UHFFFAOYSA-N 2-(1-methoxypropan-2-yl)-3-methylsulfanyl-1H-1,2,4-triazol-5-one Chemical compound CC(COC)N1N=C(N=C1SC)O FOIFBEVHAOADFO-UHFFFAOYSA-N 0.000 description 1
- 241000238888 Argasidae Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000907223 Bruchinae Species 0.000 description 1
- 241000257161 Calliphoridae Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241001466044 Delphacidae Species 0.000 description 1
- 241001481702 Dermanyssidae Species 0.000 description 1
- 241000131287 Dermestidae Species 0.000 description 1
- 241001414830 Diaspididae Species 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000238816 Gryllidae Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241001124557 Lymantriidae Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000257226 Muscidae 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
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001415279 Pseudococcidae Species 0.000 description 1
- 241000258921 Pulicidae Species 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- 241001124072 Reduviidae Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- 241000254062 Scarabaeidae Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000896028 Tettigoniidae Species 0.000 description 1
- 241000130767 Tineidae Species 0.000 description 1
- 241000131339 Tipulidae Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- -1 tackifiers Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
Abstract of the Disclosure 1,2,4-Triazole derivatives of the formula
Description
10743;~
The present invention provides derivatives of 1,2,4-triazole, a process for the manufacture thereof, and a method of controlling pests which comprises the use of these derivatives.
` S The 1,2,4-triazole derivatives have the formula :~ CH30C~I2 ~CH3 H
~ o-i~
wherein each of Rl, R2 and R3 represents a Cl-C6-alkyl group and X represents an oxygen or sulphur atom.
The alkyl groups represented by Rl to R3 can be straight-chain or branched. Examples of such groups include:
methyl, ethyl. propyl, iso-propyl, n-butyl, iso-butyl, sec.
butyl, tert. butyl, n-pentyl, n-hexyl and isomers thereof.
Preferred compounds on account of their action are those of the formula I, wherein each of Rl, R2 and R3 represents a methyl or ethyl group and X represents a sulphur atom.
The compounds of the formula I can be obtained by methods which are known per se, for example as follows:
. ~
.
., . ~, , ~ . -.
.. . - . -., ~ ~ ~ , . .. .
1(~7432~ .
~ 3 X
A) IN N + Hal-P ' 1 acid acceptor ~ I
(III) (II) 30CH~ / CH3 X
,CH " / OR
B) N N ~ Hal-P
R 3S ~ N OMe ~ -(IV) ~III) In the formulae II, III and IV, the symbols Rl to R3 ; and X are as defined for formula I and Hal represents a halogen atomJ preferably a chlorine or bromine atom, and Me represents an alkali metal, ammonium or trialkylammoniu~.
Suitable acid acceptors are for example the following bases: tertiary amines, such as triethylamine, dimethyl aniline, pyridine; inorganic bases, such as hydroxides and carbonates of alkali metals and alkaline earth metals, preferably sodium and potassium carbonate.
Processes A and B are carried out at a reaction temperature of 0 to 120C, preferably at 20 to 80C, at normal pressure and in solvents or diluents. Suitable solvents 10743Z~i or diluents are for example: ethers and ethereal compounds, such as diethyl ether, dipropyl ether, dioxan, dimethoxy-ethane, tetrahydrofuranei amides, such as N,N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, chloroform, chloro-benzenei nitriles, such as acetonitrile; dimethyl sulphoxide;
ketones, such as acetone, methyl ethyl ketone,and water.
The starting materials of the formula III are known.
They can be prepared in analogy to known processes.
The starting materials of the formula II and IV are new and can be prepared according to the following known reaction scheme:
3 \C/ 3 hydrogen + 3 ~CH 3 " catalyst NH
N ~ ^ b H~O ~ e.g. palladium-calcium NHCOOC2u5 N C OC2 5 carbonate or platinum~carbon ~V) (VI) ¦ ClCN
l NaHC03 3 ~2~ 3 NC-N
(Vll) . ~
7~3;~
NaSR3 3 2 ~CH CH30CH2 ~ 3 Vll (VIII) ~35 N QH ~35 OMe CII) ~IV) In the formulae II, IV to VIII, R3 is as defined in formula I and Me represents an alkali metal. The reaction of the compound VII with the compound VIII is carried out in a solvent at 10 to 120C, preferably at 20 to 90C, and lasts a few minutes to several hours, depending on the sub-stituents and reaction conditions. Suitable solvents are for example ketones, such as acetone or methyl ethyl ketone;
tetrahydrofurane, and water.
The active substances of the formula I are suitable for controlling a variety of animal and plant pests. Thus they possess nematocidal properties and can be used for example, for controlling phytopathogenic nematodes. The active sub-stances of the formula I are also partly suitable for use as herbi-cides and plant regulators and for controlling viruses, bacteria, and phytopathogenic fungi. Above all, however, they act on all development stages, such as eggs, larvae, nymphs pupae and adults, of insects and representatives of the order Acarina, such as mites and ticks.
.
10743'~i The compounds of the formula I have, for example, a lethal or repellant action on the following insects or representatives of the order Acarina:
Blattidae, Gryllidae, ~ryllotalpidae, Tettigoniidae, Cimicidae, Pyrrhocoridae, Reduviidae, Aphididae, Delphacidae, Diaspididae, Pseudococcidae, Chrysomilidae, Coccinellidae, Bruchidae, Scarabaeidae, Dermestidae, Tenebrionidae, Tineidae, Noctuidae, Lymantriidae, Pyralidae, Culicidae, Tipulidae, Stomoxydae, Muscidae, Calliphoridae, Trypetidae, and Pulicidae, and of the families: Txodidae, Argasidae, Tetranychidae and Dermanyssidae .
The acaricidal and/or insecticidal action can be sub-stantially broadened and adjusted to prevailing conditions by adding other insecticides and/or acaricides.
Examples of suitable additives include: nitrophenols and derivatives thereof; formamidinesi ureasi pyrethroids;
carbamates and chlorinated hydrocarbons.
The compounds of formula I can be used as pur~ active substance or together with suitable carriers and/or additives.
Suitable additives can be solid or liquid and correspond to the substances conventionally used in the art of formulation, such as natural or regenerated substances, solvents, disper-sants, wetting agents, tackifiers, thickeners, binding agents and/or fertilizers. For application, the compounds of the ~0~7~3Z6 formula I can be processed to dusts, emulsion concentrates, granulates, dispersions, sprays, to solutions and suspensions in the conventional formulations, which are co~monly employed in application technology. Mention is also to be made of cattle dips and spray races, in which aqueous preparations are used.
The compositions of the present invention are ob-tained in known manner by intimately mixing and/or grinding active substances of formula I with the suitable carriers, with or without the addition of dispersants or so~vents which are inert to the active substances.
The active substances can be in the form of and used in the following application forms:
Solids: dusts, tracking agents, granulates (coated granulates, impregnated granulates and homogeneous granulates) Liquids:
a) active substance concentrates which are dispersible in water: wettable powders, pastes, emulsionsi b) solutions:
The content of active substances in the compositions describ-ed above is between 0.1 and 95%.
The active substances of formula I can for example be formulated as follows:
107432~i Dust:
The following substances are used to prepare (a~ a 5% and (b) a 25% dust:
a)5 parts of active substance, 95 parts of talcum.
b)2 parts of active substance, 1 part of highly dispersed silicic acid, 97 parts of talcum.
The active substance are mixed with the carriers and ground.
Granulate:
The following ingredients are used to prepare a 5% granulate:
5 parts of active substance, 0.25 part of epichlorohydrine, 0.25 part of cetyl polyglycol ether, 3.50 parts of polyethylene glycol, 91 parts of kaolin (particle size 0.3 to 0.8 mm).
The active substance is mixed with epichlorohydrin and dissolved in 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The resultant solution is sprayed onto kaolin and the acetone is subsequently evaporated in vacuo.
Wettable Powder:
The following ingredients are used to prepare a) a 40%, b) and c) a 25% and d) a 10% ~ettable powder:
.
107432~i a) 40 parts of active substance, 5 parts of sodium lignin sulphona~e, 1 part of sodium dibu~yl-naphthalene sulphonate, 54 parts of silicic acid;
5 b) 25 parts of active substance~
4.5 parts of calcium lignin sulphonate, 1.9 parts of Champagne-chalk/hydroxyethylcellulose mixture (1:1), 1.5 parts of sodium dibutyl-naphthalenesulphonate, 19.5 parts of silicic acid, 19.5 parts of Champagne-chalk, 28.1 parts of kaolini c) 25 parts of active substance,
The present invention provides derivatives of 1,2,4-triazole, a process for the manufacture thereof, and a method of controlling pests which comprises the use of these derivatives.
` S The 1,2,4-triazole derivatives have the formula :~ CH30C~I2 ~CH3 H
~ o-i~
wherein each of Rl, R2 and R3 represents a Cl-C6-alkyl group and X represents an oxygen or sulphur atom.
The alkyl groups represented by Rl to R3 can be straight-chain or branched. Examples of such groups include:
methyl, ethyl. propyl, iso-propyl, n-butyl, iso-butyl, sec.
butyl, tert. butyl, n-pentyl, n-hexyl and isomers thereof.
Preferred compounds on account of their action are those of the formula I, wherein each of Rl, R2 and R3 represents a methyl or ethyl group and X represents a sulphur atom.
The compounds of the formula I can be obtained by methods which are known per se, for example as follows:
. ~
.
., . ~, , ~ . -.
.. . - . -., ~ ~ ~ , . .. .
1(~7432~ .
~ 3 X
A) IN N + Hal-P ' 1 acid acceptor ~ I
(III) (II) 30CH~ / CH3 X
,CH " / OR
B) N N ~ Hal-P
R 3S ~ N OMe ~ -(IV) ~III) In the formulae II, III and IV, the symbols Rl to R3 ; and X are as defined for formula I and Hal represents a halogen atomJ preferably a chlorine or bromine atom, and Me represents an alkali metal, ammonium or trialkylammoniu~.
Suitable acid acceptors are for example the following bases: tertiary amines, such as triethylamine, dimethyl aniline, pyridine; inorganic bases, such as hydroxides and carbonates of alkali metals and alkaline earth metals, preferably sodium and potassium carbonate.
Processes A and B are carried out at a reaction temperature of 0 to 120C, preferably at 20 to 80C, at normal pressure and in solvents or diluents. Suitable solvents 10743Z~i or diluents are for example: ethers and ethereal compounds, such as diethyl ether, dipropyl ether, dioxan, dimethoxy-ethane, tetrahydrofuranei amides, such as N,N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, chloroform, chloro-benzenei nitriles, such as acetonitrile; dimethyl sulphoxide;
ketones, such as acetone, methyl ethyl ketone,and water.
The starting materials of the formula III are known.
They can be prepared in analogy to known processes.
The starting materials of the formula II and IV are new and can be prepared according to the following known reaction scheme:
3 \C/ 3 hydrogen + 3 ~CH 3 " catalyst NH
N ~ ^ b H~O ~ e.g. palladium-calcium NHCOOC2u5 N C OC2 5 carbonate or platinum~carbon ~V) (VI) ¦ ClCN
l NaHC03 3 ~2~ 3 NC-N
(Vll) . ~
7~3;~
NaSR3 3 2 ~CH CH30CH2 ~ 3 Vll (VIII) ~35 N QH ~35 OMe CII) ~IV) In the formulae II, IV to VIII, R3 is as defined in formula I and Me represents an alkali metal. The reaction of the compound VII with the compound VIII is carried out in a solvent at 10 to 120C, preferably at 20 to 90C, and lasts a few minutes to several hours, depending on the sub-stituents and reaction conditions. Suitable solvents are for example ketones, such as acetone or methyl ethyl ketone;
tetrahydrofurane, and water.
The active substances of the formula I are suitable for controlling a variety of animal and plant pests. Thus they possess nematocidal properties and can be used for example, for controlling phytopathogenic nematodes. The active sub-stances of the formula I are also partly suitable for use as herbi-cides and plant regulators and for controlling viruses, bacteria, and phytopathogenic fungi. Above all, however, they act on all development stages, such as eggs, larvae, nymphs pupae and adults, of insects and representatives of the order Acarina, such as mites and ticks.
.
10743'~i The compounds of the formula I have, for example, a lethal or repellant action on the following insects or representatives of the order Acarina:
Blattidae, Gryllidae, ~ryllotalpidae, Tettigoniidae, Cimicidae, Pyrrhocoridae, Reduviidae, Aphididae, Delphacidae, Diaspididae, Pseudococcidae, Chrysomilidae, Coccinellidae, Bruchidae, Scarabaeidae, Dermestidae, Tenebrionidae, Tineidae, Noctuidae, Lymantriidae, Pyralidae, Culicidae, Tipulidae, Stomoxydae, Muscidae, Calliphoridae, Trypetidae, and Pulicidae, and of the families: Txodidae, Argasidae, Tetranychidae and Dermanyssidae .
The acaricidal and/or insecticidal action can be sub-stantially broadened and adjusted to prevailing conditions by adding other insecticides and/or acaricides.
Examples of suitable additives include: nitrophenols and derivatives thereof; formamidinesi ureasi pyrethroids;
carbamates and chlorinated hydrocarbons.
The compounds of formula I can be used as pur~ active substance or together with suitable carriers and/or additives.
Suitable additives can be solid or liquid and correspond to the substances conventionally used in the art of formulation, such as natural or regenerated substances, solvents, disper-sants, wetting agents, tackifiers, thickeners, binding agents and/or fertilizers. For application, the compounds of the ~0~7~3Z6 formula I can be processed to dusts, emulsion concentrates, granulates, dispersions, sprays, to solutions and suspensions in the conventional formulations, which are co~monly employed in application technology. Mention is also to be made of cattle dips and spray races, in which aqueous preparations are used.
The compositions of the present invention are ob-tained in known manner by intimately mixing and/or grinding active substances of formula I with the suitable carriers, with or without the addition of dispersants or so~vents which are inert to the active substances.
The active substances can be in the form of and used in the following application forms:
Solids: dusts, tracking agents, granulates (coated granulates, impregnated granulates and homogeneous granulates) Liquids:
a) active substance concentrates which are dispersible in water: wettable powders, pastes, emulsionsi b) solutions:
The content of active substances in the compositions describ-ed above is between 0.1 and 95%.
The active substances of formula I can for example be formulated as follows:
107432~i Dust:
The following substances are used to prepare (a~ a 5% and (b) a 25% dust:
a)5 parts of active substance, 95 parts of talcum.
b)2 parts of active substance, 1 part of highly dispersed silicic acid, 97 parts of talcum.
The active substance are mixed with the carriers and ground.
Granulate:
The following ingredients are used to prepare a 5% granulate:
5 parts of active substance, 0.25 part of epichlorohydrine, 0.25 part of cetyl polyglycol ether, 3.50 parts of polyethylene glycol, 91 parts of kaolin (particle size 0.3 to 0.8 mm).
The active substance is mixed with epichlorohydrin and dissolved in 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The resultant solution is sprayed onto kaolin and the acetone is subsequently evaporated in vacuo.
Wettable Powder:
The following ingredients are used to prepare a) a 40%, b) and c) a 25% and d) a 10% ~ettable powder:
.
107432~i a) 40 parts of active substance, 5 parts of sodium lignin sulphona~e, 1 part of sodium dibu~yl-naphthalene sulphonate, 54 parts of silicic acid;
5 b) 25 parts of active substance~
4.5 parts of calcium lignin sulphonate, 1.9 parts of Champagne-chalk/hydroxyethylcellulose mixture (1:1), 1.5 parts of sodium dibutyl-naphthalenesulphonate, 19.5 parts of silicic acid, 19.5 parts of Champagne-chalk, 28.1 parts of kaolini c) 25 parts of active substance,
2.5 parts of isooctylphenoxy-polyethylene-ethanol, 1.7 parts of Champagne-chalk/hydroxyethylcellulose mixture (1:1), 8.3 parts of sodium aluminium silicate, 16.5 parts of kieselguhr, 46 parts of kaolin;
20 d) 10 parts of active substance,
20 d) 10 parts of active substance,
3 parts of a mixture of sodium salts of saturated fatty alcohol sulphonates, 5 parts of naphthalenesulphonic acid/formaldehyde condensate, 82 parts of kaolin.
- _ g _ ,:, 1~)7432~
The active substances are intimately mixed with the additives in suitable mixers and ground in appropriate mills and rollers to yield wettable powders, which can be diluted with water to give suspensions of the required concentration.
Emulsifiable concentrates -The following substances are used to prepare a) a 10%, b) a 25%, c) a 50% emulsifiable concentrate:
a) 10 parts of active substance, 3.4 parts of epoxidised vegetable oil, 3.4 parts of a combination emulsifier, composed of fatty alcohol polyglycol ether and calcium alkylarylsulphona~e, 40 parts of dimethyl formamide, 43.2 parts of xylene;
15 b) 25 parts of active substance, 2.5 parts of epoxidised vegetable oil, 10 parts of an alkylarylsulphonate/fatty alcohol polyglycol ether mixture, 5 parts of dimethyl formamide 57.5 parts of xylenei c) 50 parts of active substance,
- _ g _ ,:, 1~)7432~
The active substances are intimately mixed with the additives in suitable mixers and ground in appropriate mills and rollers to yield wettable powders, which can be diluted with water to give suspensions of the required concentration.
Emulsifiable concentrates -The following substances are used to prepare a) a 10%, b) a 25%, c) a 50% emulsifiable concentrate:
a) 10 parts of active substance, 3.4 parts of epoxidised vegetable oil, 3.4 parts of a combination emulsifier, composed of fatty alcohol polyglycol ether and calcium alkylarylsulphona~e, 40 parts of dimethyl formamide, 43.2 parts of xylene;
15 b) 25 parts of active substance, 2.5 parts of epoxidised vegetable oil, 10 parts of an alkylarylsulphonate/fatty alcohol polyglycol ether mixture, 5 parts of dimethyl formamide 57.5 parts of xylenei c) 50 parts of active substance,
4.2 parts of tributylphenol polyglycol ether, ~.5 parts of calcium dodecylbenzenesulfonate, 20 parts of cyclohexanone, 20 parts of xylene.
- ~O -107432~ `
Emulsions of any required concentration can be prepared by diluting the above described concentrates with water.
Spray The following ingredients are used to prepare a) a 5% and b) a 95% spray a) 5 parts of active substance, 1 part of epichlorohydrin, 94 parts of ligroin (boiling range 160-190C);
b) 95 parts of active substance,
- ~O -107432~ `
Emulsions of any required concentration can be prepared by diluting the above described concentrates with water.
Spray The following ingredients are used to prepare a) a 5% and b) a 95% spray a) 5 parts of active substance, 1 part of epichlorohydrin, 94 parts of ligroin (boiling range 160-190C);
b) 95 parts of active substance,
5 parts of epichlorohydrin.
The following Examples will serve to illustrate the invention in more detail.
1~7432f~i Example 1 a) Preparation of l-(l'-methyl-2'-methoxy-ethyl)-3-hydroxy-5-methylthio-1,2,4-triazole 0.5 Mole of the compound of the formula C~30C~l2~c~ C~13 N ~ ooC2~T5 CN
(n20 = l.47~.2) is added dropwise at room temperature to a solution consisting of 0.5 mole of sodium hydroxide in 100 ml of water and into which 0.5 mole of CH3SH has been introduced. The reaction proceeds exothermically (70C). The reaction mixture is keptforl hour at 80C. After cooling, the product which crystallises out is collected by filtration and recrystallised from ether/
hexane to yield the compound of the formula 3 `2CH C~13 N - N
CH3S ~N ~ 0ll with a melting point of 102-104C. The compound of the formula C~330C~2 ~ CH3 N-- N
2 5 ~N~ 011 10743Zf~
(m.p. 94-96C) is obtained in analogous manner.
b) Preparation of 0,0-diethyl-0-~1-(1'-methyl-2'-methoxy-ethyl)-5-methylthio-1,2,4-triazolyl-(3)-thiophosphoric acid ester _ .
0.1 mole of 1-(1'-methyl-2'-methoxy-ethyl)-3-hydroxy-5-methylthio-1,2,4-triazole and 0.1 mole of potassium carbonate in 200 ml of methyl ethyl ketone are refluxed for 2 hours.
After the dropwise addition of 0.1 mole of diethylthiophos-phoric chloride at 40C, the mixture is refluxed once more for 2 hours, then left to stand for 15 hours at 20C. The salts are filtered off and the filtrate is concentrated in vacuo. The oiiy residue is purified through a column of silica gel with chloroform as eluant to yield the compound of the formula Cll30C~l2 / CH3 N - N
CH3S~ P(C2~l5)2 in the form of an oil with a refractive index of n20= 1.5033.
The following compounds are obtained in analogous manner:
10-~3Z6i CH30CH2~CH~ CH3 C2H5S~N ~P COC2H5) 2 n D = 1.5072 CH30CH2~CH~CH3 N--N S
(oc2H5)2 nD20 = 1.4970 3 2 \ ~CH3 --N
3 2 J~ ~L ,S, nD20 = 1.4935 3 2 \ / CH3 CH
~_ N S
2 5 J~NJI O-P(OC4Hg(n))2 nD20 = 1.4960 ,CH nD20 = 1.4770 C2H5S ~N/J O-P (C2H5) 2 CH
C2H5S~ N~LO-P(OCH3)2 nD - 1.5025 1074~
Example 2 A) Insec~icidal stomach poison action Cotton plants were sprayed with a 0.05% aqueous emulsion of active substance (obtained from a 10% emulsifiable concentrace).
After the spray coating had dried, the cotton plants were populated respectively with Spodoptera littoralis and Heliothis virescens larvae in the L3 stage.
In this test, the compounds of Example lb exhibited a good insecticidal stomach poison action on Spodoptera and Heliothis larvae.
B) System insecticidal action The systemic action was determined by immersing rooted bean plants (Vicia faba) in a 0.01% aqueous solution of active substance (obtained from a 10% emulsifiable concentrate).
After 24 hours the parts of the plants above the soil were populated with aphids (Aphis fabae). The aphids were protected from the contact and gas action by a special dev;ce. The test was carried out at 24C and 70% relative humidity.
In this test, the compounds of Example lb exhibited systemic insecticidal action on Aphis fabae.
Example 3 Action on Chilo suppressalis Six rice plants of the variety Caloro were transplanted into 10~3'~
each of a number of plastic pots having a diameter of 17 cm at the top, and reared to a height of approx. 60 cm. Infestation with larvae of Chilo suppressalis (Ll stage; 3 to 4 ~ in length) took place 2 days after the active substance had been added to the paddy water in granulate form (rate of application 8 kg of active substance/hectare). Evaluation of the insect-icidal action took place 10 days after addition of the granulate. The compounds of formula Ib acted in this test on Chilo suppressalis.
Example 4 Acaricidal action Phaseolus vulgaris (dwarf beans) had an infested piece of leaf from a mass culture of tetranychus urticae placed on them 12 hours before the test for the acaricidal action.
The mobile stages which had migrated to the plants were sprayed with the emulsified test preparations from a chroma-tography atomiser so that the sprayed preparation did not run off. The number of living and dead larvae, adults and eggs were evaluated after 2 to 7 days under a stereoscopic micro-scope and the result expressed in percentages. During thecourse of the test, the treated plants were kept in green-house compartments at 25C. The compounds of Example lb acted in the above test on eggs, larvae and adults of Tetranychus urticae.
107432~i Example 5 Action on soil nematodes The action on soil nematodes was tested by applying the active substances in the respe~tive concentration indicated to and intimately mixing them with soil infected with root gall nematodes (Meloidgyne arenaria). Im~ediately afterwards, tomato cuttings were planted in the thus prepared soil in a test run and after 8 days tomato seeds were sown in another test run.
In order to assess the nematocidal action, the galls present on the roots were counted 28 days after planting and sowing respectively. In this test the compounds according to Example lb exhibited good action on Meloidgyne arenaria.
EY.ample 6 Action on ticks A) Rhipicephalus bursa Five adult ticks and 50 tick larvae were counted into each of a number of test tubes and imersed for l to 2 minutes in 2 ml of an aqueous emulsion containing a concentration of lO0, lO, l or O.l ppm of test substance. Each test tube was then sealed with a cotton-wool plug and placed on its head to enable the cotton wool to absorb the acti~e substance emulsion.
The adults were evaluated after 2 wee'~s and the larvae after 2 days. Each ~est was repeated twice.
lOt7~3~
B) Boophilus_~icroDI~s (larvae) Tests were carried out on 20 OP- sensitive and 20 OP-resistant larvae with aqueous emulsions similar to those used in test A.
(The resistance refers to the tolerance towards diazinone).
The compounds of Example lb acted in these tests on adults and larvae of Rhipicephalus bursa and OP-sensitive and of resistant larvae of Boophilus microplus.
Example 7 Action of Erysiphe ~raminis on Hordeum vulgare Barley plants (approx. 8 cm in height) were sprayed with a spray broth (active subs~ance content: 0.05%) prepared from a wettable powder of the active substance.
After 48 hours the trea~ed plants were dusted with conidia of the fungus. The infec~ed barley plants were stood in a green-house at approx. 22C and the fungus attack was evaluatedafter 10 days.
The compounds of Example lb acted in this test on Erysiphe graminis.
The following Examples will serve to illustrate the invention in more detail.
1~7432f~i Example 1 a) Preparation of l-(l'-methyl-2'-methoxy-ethyl)-3-hydroxy-5-methylthio-1,2,4-triazole 0.5 Mole of the compound of the formula C~30C~l2~c~ C~13 N ~ ooC2~T5 CN
(n20 = l.47~.2) is added dropwise at room temperature to a solution consisting of 0.5 mole of sodium hydroxide in 100 ml of water and into which 0.5 mole of CH3SH has been introduced. The reaction proceeds exothermically (70C). The reaction mixture is keptforl hour at 80C. After cooling, the product which crystallises out is collected by filtration and recrystallised from ether/
hexane to yield the compound of the formula 3 `2CH C~13 N - N
CH3S ~N ~ 0ll with a melting point of 102-104C. The compound of the formula C~330C~2 ~ CH3 N-- N
2 5 ~N~ 011 10743Zf~
(m.p. 94-96C) is obtained in analogous manner.
b) Preparation of 0,0-diethyl-0-~1-(1'-methyl-2'-methoxy-ethyl)-5-methylthio-1,2,4-triazolyl-(3)-thiophosphoric acid ester _ .
0.1 mole of 1-(1'-methyl-2'-methoxy-ethyl)-3-hydroxy-5-methylthio-1,2,4-triazole and 0.1 mole of potassium carbonate in 200 ml of methyl ethyl ketone are refluxed for 2 hours.
After the dropwise addition of 0.1 mole of diethylthiophos-phoric chloride at 40C, the mixture is refluxed once more for 2 hours, then left to stand for 15 hours at 20C. The salts are filtered off and the filtrate is concentrated in vacuo. The oiiy residue is purified through a column of silica gel with chloroform as eluant to yield the compound of the formula Cll30C~l2 / CH3 N - N
CH3S~ P(C2~l5)2 in the form of an oil with a refractive index of n20= 1.5033.
The following compounds are obtained in analogous manner:
10-~3Z6i CH30CH2~CH~ CH3 C2H5S~N ~P COC2H5) 2 n D = 1.5072 CH30CH2~CH~CH3 N--N S
(oc2H5)2 nD20 = 1.4970 3 2 \ ~CH3 --N
3 2 J~ ~L ,S, nD20 = 1.4935 3 2 \ / CH3 CH
~_ N S
2 5 J~NJI O-P(OC4Hg(n))2 nD20 = 1.4960 ,CH nD20 = 1.4770 C2H5S ~N/J O-P (C2H5) 2 CH
C2H5S~ N~LO-P(OCH3)2 nD - 1.5025 1074~
Example 2 A) Insec~icidal stomach poison action Cotton plants were sprayed with a 0.05% aqueous emulsion of active substance (obtained from a 10% emulsifiable concentrace).
After the spray coating had dried, the cotton plants were populated respectively with Spodoptera littoralis and Heliothis virescens larvae in the L3 stage.
In this test, the compounds of Example lb exhibited a good insecticidal stomach poison action on Spodoptera and Heliothis larvae.
B) System insecticidal action The systemic action was determined by immersing rooted bean plants (Vicia faba) in a 0.01% aqueous solution of active substance (obtained from a 10% emulsifiable concentrate).
After 24 hours the parts of the plants above the soil were populated with aphids (Aphis fabae). The aphids were protected from the contact and gas action by a special dev;ce. The test was carried out at 24C and 70% relative humidity.
In this test, the compounds of Example lb exhibited systemic insecticidal action on Aphis fabae.
Example 3 Action on Chilo suppressalis Six rice plants of the variety Caloro were transplanted into 10~3'~
each of a number of plastic pots having a diameter of 17 cm at the top, and reared to a height of approx. 60 cm. Infestation with larvae of Chilo suppressalis (Ll stage; 3 to 4 ~ in length) took place 2 days after the active substance had been added to the paddy water in granulate form (rate of application 8 kg of active substance/hectare). Evaluation of the insect-icidal action took place 10 days after addition of the granulate. The compounds of formula Ib acted in this test on Chilo suppressalis.
Example 4 Acaricidal action Phaseolus vulgaris (dwarf beans) had an infested piece of leaf from a mass culture of tetranychus urticae placed on them 12 hours before the test for the acaricidal action.
The mobile stages which had migrated to the plants were sprayed with the emulsified test preparations from a chroma-tography atomiser so that the sprayed preparation did not run off. The number of living and dead larvae, adults and eggs were evaluated after 2 to 7 days under a stereoscopic micro-scope and the result expressed in percentages. During thecourse of the test, the treated plants were kept in green-house compartments at 25C. The compounds of Example lb acted in the above test on eggs, larvae and adults of Tetranychus urticae.
107432~i Example 5 Action on soil nematodes The action on soil nematodes was tested by applying the active substances in the respe~tive concentration indicated to and intimately mixing them with soil infected with root gall nematodes (Meloidgyne arenaria). Im~ediately afterwards, tomato cuttings were planted in the thus prepared soil in a test run and after 8 days tomato seeds were sown in another test run.
In order to assess the nematocidal action, the galls present on the roots were counted 28 days after planting and sowing respectively. In this test the compounds according to Example lb exhibited good action on Meloidgyne arenaria.
EY.ample 6 Action on ticks A) Rhipicephalus bursa Five adult ticks and 50 tick larvae were counted into each of a number of test tubes and imersed for l to 2 minutes in 2 ml of an aqueous emulsion containing a concentration of lO0, lO, l or O.l ppm of test substance. Each test tube was then sealed with a cotton-wool plug and placed on its head to enable the cotton wool to absorb the acti~e substance emulsion.
The adults were evaluated after 2 wee'~s and the larvae after 2 days. Each ~est was repeated twice.
lOt7~3~
B) Boophilus_~icroDI~s (larvae) Tests were carried out on 20 OP- sensitive and 20 OP-resistant larvae with aqueous emulsions similar to those used in test A.
(The resistance refers to the tolerance towards diazinone).
The compounds of Example lb acted in these tests on adults and larvae of Rhipicephalus bursa and OP-sensitive and of resistant larvae of Boophilus microplus.
Example 7 Action of Erysiphe ~raminis on Hordeum vulgare Barley plants (approx. 8 cm in height) were sprayed with a spray broth (active subs~ance content: 0.05%) prepared from a wettable powder of the active substance.
After 48 hours the trea~ed plants were dusted with conidia of the fungus. The infec~ed barley plants were stood in a green-house at approx. 22C and the fungus attack was evaluatedafter 10 days.
The compounds of Example lb acted in this test on Erysiphe graminis.
Claims (14)
1. A 1,2,4-triazole of the formula wherein each of R1, R2 and R3 represents a C1-C6-alkyl group and X represents an oxygen or sulphur atom.
2. A 1,2,4-triazole according to claim 1, wherein each of R1, R2 and R3 represents a methyl or ethyl group and X
represents a sulphur atom.
represents a sulphur atom.
3. A 1,2,4-triazole according to claim 2 of the formula
4. A 1,2,4-triazole according to claim 2 of the formula
5. A 1,2,4-triazo1e according to claim 1 of the formula
6. A 1,2,4-triazole according to claim 1 of the formula
7. A 1,2,4-triazole according to claim 1 of the formula
8. A 1,2,4-triazole according to claim 1 of the formula
9. A 1,2,4-triazole according to claim 1 of the formula
10. A process for the manufacture of compounds according to claim 1, wherein a compound of the formula wherein R1, R2 and X are as defined in claim 1 and Hal represents a halogen atom, is reacted with a compound of the formula wherein R3 is as defined in claim 1 and Me represents a hydrogen atom or alkali metal, ammonium or trialkylammonium, optionally in the presence of an acid acceptor.
11. A method of controlling animal and plant pests, which comprises contacting the pests with a compound as claimed in claim 1.
12. A method according to claim 11, wherein the pests to be control-led are insects and representatives of the order Acarina.
13. A method according to claim 11, wherein the pests to be control-led are phytopathogenic nematodes.
14. A method according to claim 11, wherein the pests to be control-led are phytopathogenic fungi.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1479675A CH602012A5 (en) | 1975-11-14 | 1975-11-14 | (5)-Alkylthio-(1,2,4)-triazolyl-(3)-(thio)phosphates |
CH1200276 | 1976-09-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1074326A true CA1074326A (en) | 1980-03-25 |
Family
ID=25709393
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA265,476A Expired CA1074326A (en) | 1975-11-14 | 1976-11-12 | Esters |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS5262277A (en) |
AT (1) | AT341830B (en) |
CA (1) | CA1074326A (en) |
DE (1) | DE2651556A1 (en) |
FR (1) | FR2331566A1 (en) |
GB (1) | GB1563733A (en) |
NL (1) | NL7612543A (en) |
PH (1) | PH12226A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4265897A (en) * | 1978-11-14 | 1981-05-05 | Ciba-Geigy Corporation | N-N-Dimethyl-1-(1'-methyl-2'-methoxyethyl)-1,2,4-triazolylcarbamates |
-
1976
- 1976-11-08 FR FR7633613A patent/FR2331566A1/en active Granted
- 1976-11-11 PH PH19120A patent/PH12226A/en unknown
- 1976-11-11 NL NL7612543A patent/NL7612543A/en not_active Application Discontinuation
- 1976-11-11 DE DE19762651556 patent/DE2651556A1/en not_active Withdrawn
- 1976-11-12 AT AT844776A patent/AT341830B/en not_active IP Right Cessation
- 1976-11-12 GB GB47241/76A patent/GB1563733A/en not_active Expired
- 1976-11-12 CA CA265,476A patent/CA1074326A/en not_active Expired
- 1976-11-13 JP JP51136825A patent/JPS5262277A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
NL7612543A (en) | 1977-05-17 |
PH12226A (en) | 1978-11-29 |
ATA844776A (en) | 1977-06-15 |
GB1563733A (en) | 1980-03-26 |
FR2331566A1 (en) | 1977-06-10 |
FR2331566B1 (en) | 1978-04-14 |
AT341830B (en) | 1978-02-27 |
DE2651556A1 (en) | 1977-05-26 |
JPS5262277A (en) | 1977-05-23 |
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