CA1047489A - Esters - Google Patents
EstersInfo
- Publication number
- CA1047489A CA1047489A CA175,820A CA175820A CA1047489A CA 1047489 A CA1047489 A CA 1047489A CA 175820 A CA175820 A CA 175820A CA 1047489 A CA1047489 A CA 1047489A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- methyl
- compounds
- compound according
- locus
- 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 description 2
- 238000000034 method Methods 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 38
- 241000238876 Acari Species 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 241000500891 Insecta Species 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 239000005864 Sulphur Substances 0.000 abstract description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 239000013543 active substance Substances 0.000 description 35
- -1 diethyl e~her Chemical class 0.000 description 21
- 239000008187 granular material Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 239000000969 carrier Substances 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 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 5
- 239000007921 spray Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 241000244206 Nematoda Species 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- 239000003513 alkali Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 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 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229920000642 polymer Polymers 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
- 235000012222 talc Nutrition 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 2
- OTYZDIRNFDVXFG-UHFFFAOYSA-N (2-butylphenyl) n-methylcarbamate Chemical compound CCCCC1=CC=CC=C1OC(=O)NC OTYZDIRNFDVXFG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000534456 Arenaria <Aves> Species 0.000 description 2
- 241000902805 Aulacophora Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000426499 Chilo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000089742 Citrus aurantifolia Species 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- PGJBQBDNXAZHBP-UHFFFAOYSA-N Dimefox Chemical compound CN(C)P(F)(=O)N(C)C PGJBQBDNXAZHBP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 101100456896 Drosophila melanogaster metl gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SPJOZZSIXXJYBT-UHFFFAOYSA-N Fenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=CC=C1 SPJOZZSIXXJYBT-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
- 241000238680 Rhipicephalus microplus Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
- 235000019993 champagne Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 2
- VEENJGZXVHKXNB-VOTSOKGWSA-N dicrotophos Chemical compound COP(=O)(OC)O\C(C)=C\C(=O)N(C)C VEENJGZXVHKXNB-VOTSOKGWSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 229940075566 naphthalene Drugs 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 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
- 239000002245 particle Substances 0.000 description 2
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 2
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- OTKXWJHPGBRXCR-UHFFFAOYSA-N (2-chloro-4-nitrophenoxy)-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1Cl OTKXWJHPGBRXCR-UHFFFAOYSA-N 0.000 description 1
- ZAGNMMRDHSEOPE-UHFFFAOYSA-N (2-chlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1Cl ZAGNMMRDHSEOPE-UHFFFAOYSA-N 0.000 description 1
- AQWRXTQESBVJPN-UHFFFAOYSA-N (3,5-dimethyl-4-methylsulfanylphenyl)-methylcarbamic acid Chemical compound CSC1=C(C)C=C(N(C)C(O)=O)C=C1C AQWRXTQESBVJPN-UHFFFAOYSA-N 0.000 description 1
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 1
- QFBDCSDDHUBEGG-UHFFFAOYSA-N 1,2-dibutylnaphthalene;sodium Chemical compound [Na].C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 QFBDCSDDHUBEGG-UHFFFAOYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- PFGMOSOUUIZMNI-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-1-[2-[(4-chlorophenyl)methyl]-4-fluorophenyl]sulfanyl-4-fluorobenzene Chemical compound C=1C=C(Cl)C=CC=1CC1=CC(F)=CC=C1SC1=CC=C(F)C=C1CC1=CC=C(Cl)C=C1 PFGMOSOUUIZMNI-UHFFFAOYSA-N 0.000 description 1
- VUGWRLQYHXCYEE-UHFFFAOYSA-N 2-methyl-3,4-dinitrophenol;sodium Chemical compound [Na].CC1=C(O)C=CC([N+]([O-])=O)=C1[N+]([O-])=O VUGWRLQYHXCYEE-UHFFFAOYSA-N 0.000 description 1
- NSMRHYDOKZAMKJ-UHFFFAOYSA-N 3-diethoxyphosphinothioyloxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-one Chemical compound C1CCCC2=C1C1=CC=C(OP(=S)(OCC)OCC)C=C1OC2=O NSMRHYDOKZAMKJ-UHFFFAOYSA-N 0.000 description 1
- NCSZRNMVUILZEC-UHFFFAOYSA-N 3-methylidene-1,2-dihydroindene Chemical compound C1=CC=C2C(=C)CCC2=C1 NCSZRNMVUILZEC-UHFFFAOYSA-N 0.000 description 1
- HRZUJNOTWZBBQR-UHFFFAOYSA-N 4-hydroxyimino-n-methyl-1,3-dithiolane-2-carboxamide Chemical compound CNC(=O)C1SCC(=NO)S1 HRZUJNOTWZBBQR-UHFFFAOYSA-N 0.000 description 1
- NWBKWPGALSNXOJ-UHFFFAOYSA-N 5,6-dichloro-n-phenoxy-2-(trifluoromethyl)benzimidazole-1-carboxamide Chemical compound FC(F)(F)C1=NC2=CC(Cl)=C(Cl)C=C2N1C(=O)NOC1=CC=CC=C1 NWBKWPGALSNXOJ-UHFFFAOYSA-N 0.000 description 1
- WKYZOEUYCZHESZ-UHFFFAOYSA-N 6-methyl-4,6-dinitrocyclohexa-2,4-dien-1-ol Chemical compound [O-][N+](=O)C1(C)C=C([N+]([O-])=O)C=CC1O WKYZOEUYCZHESZ-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 241000132121 Acaridae Species 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000238888 Argasidae Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000907223 Bruchinae Species 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- BKAQXYNWONVOAX-UHFFFAOYSA-N Butonate Chemical compound CCCC(=O)OC(C(Cl)(Cl)Cl)P(=O)(OC)OC BKAQXYNWONVOAX-UHFFFAOYSA-N 0.000 description 1
- LVJJCQMECRPQPS-UHFFFAOYSA-N C#CCN(C)C1=CC=CC=C1N(C)C(O)=O Chemical compound C#CCN(C)C1=CC=CC=C1N(C)C(O)=O LVJJCQMECRPQPS-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000257161 Calliphoridae Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
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- 125000005270 trialkylamine group Chemical group 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Organic phosphoric acid esters of the formula
Organic phosphoric acid esters of the formula
Description
r ~ _~
.~,..... .
~o47~B5 ~ The present invention relates to organic phosphoric . ., ~; acid esters, processes for their manufacture, and to their use in pest control.
:
~ The compounds have the formula ...~, ,~,:
~ ., ~s,' ~
. .
; ~ N=N ~ ~ O P / I (I) (R4)m (R3)n wherein Rl and R2 each represents alkyl with 1 to 5 carbon atoms, R3 and R4 each represents halogen or alkyl with 1 to 5 carbon atoms, X represents oxygen or sulphur, n is zero or a number from 1 to 4, and m is zero or a number from 1 to 5.
:., By halogen is meant fluorine, chlorine, bromine, or iodine, but especially chlorine or bromine.
~' i The alkyl group Rl to R4 can be straight-chain or branched.
:
Examples of such groups include: methyl, ethyl, propyl, iso-~;~ propyl, n-, i-, sec.- and tert.-butyl, n-pentyl and isomers thereof.
:
'':
~ - 2 -.:
, , , ~ ~, : . : , The compounds ~ ~7 ~ormula I are manufactured by the following known methods:
'~ S X
la) ~ P-~Ial. + ~IO ~ ~ -N--~T ~ d--~ç-ce~t--or~ > I
(Il) (R3)n (R4)m ~(III) S X
Rl~\ 11 lb)R20~> + MeO~3N=N~
(IV) , X
;, Ha.l~ ~ N=N ~ ~ VI ~ :
- (v)(R3)n ( )R4)m 1-X
R2~ 11 0 ~ \ ~==~ + HYR ~ :
Hal ~ ~ -N=N ~ (VII) s - -- -- - ---~ I
~ (R3)n( 4)m ~ M~Rl ¦ (VI)(VIII) ..
; .
~ In the formulae II to VIII, to R4, n and m have the : meanings given for the formula I, Hal represents a halogen atom, in particular chlorine J and Me represents an alkali metal, -. especially sodium or potassium, an ammonium or alkylammonium group.
. . . - . .
. ~
n47~89 Suitable acid acceptors are: tertiary amlnes, e.g. trial-kylamine, pyridine~ dialkyl anilines; inorganic bases, e.g.
hydrides, hydroxides; carbonates and bicarbonates o-f alkali metals and alkaline earth metals. It is sometimes necessary to use catalysts in the reac~ions, for example copper or copper chloride. Processes laJ lb, and 2 are carried out at a reac-tion temperature between -2C and 130''C, at normal pressure, and in solvents or diluents.
Examples of suitable solvents or diluents are: e~her and ethereal compounds, e.g. diethyl e~her, dipropyl ether, dioxan tetrahydrofuran; amides, e.g. N,N-dialkylated carboxylic acid amides; aliphatic, aromatic, and halogenated hydrocarbons, in ~.
particular benzene, tuolene, xyleneJ chloroform, chloroben~ene;
nitriles, e.g. acetonitrile; dimethyl sulphoxide; ketones, e.g. acetone,methyl ethyl ketone; water.
The starting materials of the formulae II, III, IV, V, VII, and VIII can be manufactured in an~logous ~anner to known methods.
The compounds of the formula I have a broad biocidal act-ivity spectrum and can therefore be used for combating various plant and animal pests. In particular they are suitable for combating insects of the families: Acrididae, Blattidae, ~r~oc-10 ~ . Gryllidae, Gryllotalpidae, Tettigoniidae, Cimicidae, PLl~rrhoc oridae, Reduviidae, Aphididae, Delphacidae, Diaspididae, Pseu-doccidae, Chrysomalidae, Coccinellidae, Bruchidae, Scara~aei-dae, Dermestidae, Tenebrionidae, Curcu ionidae, Tineidae, Noctuidae, Lymantriidae, Pyralidae, Galleriidae, Culicidae, Tipulidae, Stomoxydae, Musci~ae, Calliphoridae, Trypetidae, ., , _ 4 Pulicidae J as well as Acaridae of the families: Ixodidae, Argasidae 9 Tetranychidae, Dermanyssidae. ~ -By addit;on of other insecticides and/or acaricides it ~ -- is possible to improve substan~ially the insecticidal or acaricidal action and to adapt it to given circumstances.
The follo~Jing active substances are examples of suitable ~, , additives:
. .
r, ~ Bis-O,O-diethylphosphoric aci.d anhydride (lEPP) :. - , .
Dimethyl-(2,2,2-trichloro-1-hy(lroxyetllyl)-phosphonate ~' ~
j~, (TRICHLORFON) . 1,2-dibromo-2,2-dichloroethyldimethylphosphate (N~LED) .;,~ . ~
si 2,2-dichlorovinyldimethylphosphate (DICHLORVOS)
.~,..... .
~o47~B5 ~ The present invention relates to organic phosphoric . ., ~; acid esters, processes for their manufacture, and to their use in pest control.
:
~ The compounds have the formula ...~, ,~,:
~ ., ~s,' ~
. .
; ~ N=N ~ ~ O P / I (I) (R4)m (R3)n wherein Rl and R2 each represents alkyl with 1 to 5 carbon atoms, R3 and R4 each represents halogen or alkyl with 1 to 5 carbon atoms, X represents oxygen or sulphur, n is zero or a number from 1 to 4, and m is zero or a number from 1 to 5.
:., By halogen is meant fluorine, chlorine, bromine, or iodine, but especially chlorine or bromine.
~' i The alkyl group Rl to R4 can be straight-chain or branched.
:
Examples of such groups include: methyl, ethyl, propyl, iso-~;~ propyl, n-, i-, sec.- and tert.-butyl, n-pentyl and isomers thereof.
:
'':
~ - 2 -.:
, , , ~ ~, : . : , The compounds ~ ~7 ~ormula I are manufactured by the following known methods:
'~ S X
la) ~ P-~Ial. + ~IO ~ ~ -N--~T ~ d--~ç-ce~t--or~ > I
(Il) (R3)n (R4)m ~(III) S X
Rl~\ 11 lb)R20~> + MeO~3N=N~
(IV) , X
;, Ha.l~ ~ N=N ~ ~ VI ~ :
- (v)(R3)n ( )R4)m 1-X
R2~ 11 0 ~ \ ~==~ + HYR ~ :
Hal ~ ~ -N=N ~ (VII) s - -- -- - ---~ I
~ (R3)n( 4)m ~ M~Rl ¦ (VI)(VIII) ..
; .
~ In the formulae II to VIII, to R4, n and m have the : meanings given for the formula I, Hal represents a halogen atom, in particular chlorine J and Me represents an alkali metal, -. especially sodium or potassium, an ammonium or alkylammonium group.
. . . - . .
. ~
n47~89 Suitable acid acceptors are: tertiary amlnes, e.g. trial-kylamine, pyridine~ dialkyl anilines; inorganic bases, e.g.
hydrides, hydroxides; carbonates and bicarbonates o-f alkali metals and alkaline earth metals. It is sometimes necessary to use catalysts in the reac~ions, for example copper or copper chloride. Processes laJ lb, and 2 are carried out at a reac-tion temperature between -2C and 130''C, at normal pressure, and in solvents or diluents.
Examples of suitable solvents or diluents are: e~her and ethereal compounds, e.g. diethyl e~her, dipropyl ether, dioxan tetrahydrofuran; amides, e.g. N,N-dialkylated carboxylic acid amides; aliphatic, aromatic, and halogenated hydrocarbons, in ~.
particular benzene, tuolene, xyleneJ chloroform, chloroben~ene;
nitriles, e.g. acetonitrile; dimethyl sulphoxide; ketones, e.g. acetone,methyl ethyl ketone; water.
The starting materials of the formulae II, III, IV, V, VII, and VIII can be manufactured in an~logous ~anner to known methods.
The compounds of the formula I have a broad biocidal act-ivity spectrum and can therefore be used for combating various plant and animal pests. In particular they are suitable for combating insects of the families: Acrididae, Blattidae, ~r~oc-10 ~ . Gryllidae, Gryllotalpidae, Tettigoniidae, Cimicidae, PLl~rrhoc oridae, Reduviidae, Aphididae, Delphacidae, Diaspididae, Pseu-doccidae, Chrysomalidae, Coccinellidae, Bruchidae, Scara~aei-dae, Dermestidae, Tenebrionidae, Curcu ionidae, Tineidae, Noctuidae, Lymantriidae, Pyralidae, Galleriidae, Culicidae, Tipulidae, Stomoxydae, Musci~ae, Calliphoridae, Trypetidae, ., , _ 4 Pulicidae J as well as Acaridae of the families: Ixodidae, Argasidae 9 Tetranychidae, Dermanyssidae. ~ -By addit;on of other insecticides and/or acaricides it ~ -- is possible to improve substan~ially the insecticidal or acaricidal action and to adapt it to given circumstances.
The follo~Jing active substances are examples of suitable ~, , additives:
. .
r, ~ Bis-O,O-diethylphosphoric aci.d anhydride (lEPP) :. - , .
Dimethyl-(2,2,2-trichloro-1-hy(lroxyetllyl)-phosphonate ~' ~
j~, (TRICHLORFON) . 1,2-dibromo-2,2-dichloroethyldimethylphosphate (N~LED) .;,~ . ~
si 2,2-dichlorovinyldimethylphosphate (DICHLORVOS)
2-methoxycarbamyl-1-methylvinyldimethylphospha~e (MEVINPHOS) Dimethyl-l-methyl-2-(methylcarbamoyl~vinylphosphate cis (MONOCROTOPHOS)
3-(dimethoxyphosphinyloxy)-N,N-dimethyl-cis-crotonamide (DICROTOPHOS) 2-chloro-2-diethylcarbamoyl-1-methylvinyldimethylphosphate (PHOSPHAMIDON) ,~
O,O-diethyl-O(or S)-2-(ethylthio)-ethylthiophosphate (DEMETON) ~; S-ethylthioethyl-O,O-dimethyl-dithiophosphate (THIOMETON) , .
O,O-diethyl-S-ethylmercaptomethyldithiophosphate (PHORATE) s O,O-diethyl-S-2-(ethylthio)ethyldithiophosphate (DISULFOTON) '' - ' , .
~(~47489 0,0-dime~hyl-S-2-(e~hylsulphinyJ)e~hy].~hi.ophosphate (OXYDEMI~ TON l ~ETllYI,) 0,0-dimetllyl-S-(].,2-(llcarbel:hoxyethy].di.t:hi,ol)hosphate (MALATITI ON ) O,O~O,O- tetraethyl-S,S' -methy1ene-bis-dithiol)hosphate (ET~IION) O-ethyl-S,S-dipropyldithiopllosphate O,O-clime~hyl-S (N-methyl-N-formylcarbamoylmetllyl)-dithio~ os-phate ~FORMOTIIION) O,O-dimethyl S-(N-met:hy].carbamoy].me~hyl)-dithiophosphate ..
~!)IME~TlloATE) O,O-dimethyl-O-p nitrophenylthiophosphate (P.ARATllION-I`~THYL) O,O-diethyl-O-p-nitrophenylthiophosphate (PARATHION) O~ethyl-O-p-nitrophenylphenylthiophosphate (EPN) 0,0-dimethyl-0-(4-nitro-m-tolyl)-thiophosphate (FENITnOTHION) - 15 O,O-dimethy1-0-2,4,5-~rich10ropheny1thiophosphate (P~ONNEL) O ethyl-0-2,4,5-trichlorophenylethyl~hiophosphate (TRICHLORO-NATE) 0,0-dimethyl-0-2,5-dichloro-4-bromophenylthiophosphate - (BRO~OPHOS) - -0,0-dimethyl-0-(2,5-dichloro-4-iodophenyl)-thiophosphate (JODOFENPHOS)
O,O-diethyl-O(or S)-2-(ethylthio)-ethylthiophosphate (DEMETON) ~; S-ethylthioethyl-O,O-dimethyl-dithiophosphate (THIOMETON) , .
O,O-diethyl-S-ethylmercaptomethyldithiophosphate (PHORATE) s O,O-diethyl-S-2-(ethylthio)ethyldithiophosphate (DISULFOTON) '' - ' , .
~(~47489 0,0-dime~hyl-S-2-(e~hylsulphinyJ)e~hy].~hi.ophosphate (OXYDEMI~ TON l ~ETllYI,) 0,0-dimetllyl-S-(].,2-(llcarbel:hoxyethy].di.t:hi,ol)hosphate (MALATITI ON ) O,O~O,O- tetraethyl-S,S' -methy1ene-bis-dithiol)hosphate (ET~IION) O-ethyl-S,S-dipropyldithiopllosphate O,O-clime~hyl-S (N-methyl-N-formylcarbamoylmetllyl)-dithio~ os-phate ~FORMOTIIION) O,O-dimethyl S-(N-met:hy].carbamoy].me~hyl)-dithiophosphate ..
~!)IME~TlloATE) O,O-dimethyl-O-p nitrophenylthiophosphate (P.ARATllION-I`~THYL) O,O-diethyl-O-p-nitrophenylthiophosphate (PARATHION) O~ethyl-O-p-nitrophenylphenylthiophosphate (EPN) 0,0-dimethyl-0-(4-nitro-m-tolyl)-thiophosphate (FENITnOTHION) - 15 O,O-dimethy1-0-2,4,5-~rich10ropheny1thiophosphate (P~ONNEL) O ethyl-0-2,4,5-trichlorophenylethyl~hiophosphate (TRICHLORO-NATE) 0,0-dimethyl-0-2,5-dichloro-4-bromophenylthiophosphate - (BRO~OPHOS) - -0,0-dimethyl-0-(2,5-dichloro-4-iodophenyl)-thiophosphate (JODOFENPHOS)
4-tert.butyl-2-chlorophenyl-N-me~hyl-O-methylamidophosphate (CRUFO~ATE) 0,0-dimethyl-0-(3-methyl-4-methylmercaptophenyl)-thiophosphate (FENTlIION) :
, , .
.- ~ , "''' ~ " '` ~0474ss v Xsopropylalnino-O-ethyl-O-(4-lne~ ylmercapto-3-mct:llylphenyl)- '' ,. ~ phosphate :, ',, O,O-dieLhyl-O-p-(metllylsulphirlyl)phenyl-l::hiopllosphate (]~ENSULFOTIIION)
, , .
.- ~ , "''' ~ " '` ~0474ss v Xsopropylalnino-O-ethyl-O-(4-lne~ ylmercapto-3-mct:llylphenyl)- '' ,. ~ phosphate :, ',, O,O-dieLhyl-O-p-(metllylsulphirlyl)phenyl-l::hiopllosphate (]~ENSULFOTIIION)
5 . o-p-(dilrlelllylsulphamido)-pllellyl-o~o-dillle~Lhylthiophospha1~e c~ (FAilPHUR) v O,O,O',O'-tetramethyl-O,O'-thiodi-p-phenylenethiophosphate r,., ~ .
.~,. O-ethyl-S-pllenyl-ethyldithiopllosphate ,. 0,0-dimethyl-0-(a-1nethylbenzyl-3-hydroxycrotonyl)phosphate . 10 2-chloro-1-(2,4 dichlorophenyl)vinyl-diet:hylpllosphate . (CI~LORFE:NVINPIIOS) ..
i l-chloro-1--(2,4,5-trichlorophenyl)vinyl-dimethylphosphate 0-~2-chloro-1-(2,5-dichlorophenyl)]vinyl-O,O-diethylthio-phosphate .;i 15 Phenylglyoxylonitriloxime-O,O-diethylthiophosphate (PHOXIM) i::! O,O-diethyl-O-(3-chloro-4-methyl-2-oxo-2-H-l-benzopyran-7-yl)-. thiophosphate (COUMAPHOS) 2,3-p-dioxandithiol-S~S-bis(O,O-diethyldithiophosphate) ~.
(DIOX~THION) 5-[(6-chloro-2-oxo-3-benzoxazolinyl)methyl]O,O-diethyldithio-phosph~te (PIIOSALONE) 2~(diethoxyphosphinylimino)-1,3-dithiolane . - O,O-dimethyl-S-[2-methoxy-1,3,4-thiadiazol-5-(4H)-onyl-(4)-- methyl]dithiophosphate Z5 O,O-dimethyl-9-phthalimidomethyl-dithiopllosphate (IMIDAN) ~ . , _ 7 _ ,~
, . i ,.
.-- . .
47~89 O~o-diet~ o~(3~5~6-l~r:i-chloro-2-py~-idyl)l~hio~ os~ at:e O,O-di.e~hyl O-~-pyra~inyl~hiophosplla~e (THION~ZIN) ~' 0,O~dic~hyl-0-(2-isopropyl-4-me~hyl-6-pyriT:liclyl)t:hiophosphate (DIA~XNON) 0,0-di.ethyl-0-(2-quinoxalyl)thiophosphatè
0,0-dimethyl-S-~4-oxo-1,~,3-benzotria~in~3(4I-I)-ylTnethyl)-dithiophospllate (A%INPI~OS~THYL) 0,0-dicthyl-S-(4-oY~o-1,2,3-benzotriazin-3(~II)-ylmethyl)- -dithiophosphate (AZINPHOSETllYL) S [(4,6-diamino-s triazill-2-yl)rnethyl]-0,0-dimethyldit:hio-. phosphate (ME.NAZON) .;
j' O,O-dimethyl-O (3-chloro-4-nitrophenyl)thiophosplate ` (CllLORTlIION) '' O,O-dimethyl-O(or S)-2-(etllylthioethyl)thiophosl)hate 15 (DE~ETON-S-METHYL) 2~(0~0-dimethyl-phosphoryl-thiomethyl)-5-methoxy-pyrone- --4-3,4-dichloroben~yl-triphenylphosphoniumchloride :.
0,0-diet:hyl-S-(2,5-dichlorophenylthiomethyl)dithiophosphate ' ~-' .
(PHENKAPTON) . :. .
0,0-diethyl-0-(4-methyl-cumarinyl-7`-~hiophosphate (POTASAN) $-amino bis(dimethylami~o)phosphinyl-3-phenyl-1,2,4-triazole (TRI~MIP~IOS) N-methyl-5-(0,0-dimethylthiolphosphoryl)-3-thiavaleramide ~VAMIDOTHION) 0,0-diethyl-0-12-dimethylamino-4-methylpyrimidyl-(6)]-thio- .
phosphate (DIOCTHYL) ; . .. .
, .
' , ,.. ,, ., --.. ....... .
.
- ~47489 O, O - di.methy].-S - (methy] carbalnoy1me l:hyl) - 1 hi.ophospllat:e (O`IETI~Ol~TE) i~ O -~thy1-0 - (8- quino:l i.nyl) -plleny1t~ iophosr)llonatc! (OXINOTIIIOPIIO.S) O~ etllyl-S~Illethyl--ar~ lothiophosphate (I:~ONITOR) O-methyl-O- (2,5-dichloro--4-bromoplleny:l.)-bellzoth;.ophosphate ` 5 (~IIOSVEL) O,O,O~O-tetrapropyldithiophospha~e 3-(dimethoxyphosphlnyloxy)-N-methyl-N-methoxy-cis-crotonarnide O,O--dimethyl-S-(N-ethylcarbamoylmethyl)ditlliopllosphate (ETI-lOATE-~lETHYL) O,O-diethyl-S-(N-isopropylcarbamoylme~hyl)-di.thiophos~ ate (l'ROTllOATE) S-N--(l-cyano-l-methylethyl)carbalnoylmetllylcliethyl~hiolphosplla~e (cyANTlloATE:) S-(2-acetamidoethyl)-0,0-dimethyldithiophosphate - ~-~lexamethylphosphoric acid triamide (llE~fPA) 0,0-dimethyl-O-(2-chloro-4-nitrophenyl,)thi.ophosphate (DICAPTHON) O,O-dimethyl-O-p-cyanophenyl thiophosphate (CYANOX) O-ethyl-O-p-cyanophenylthiophosphonate 0,0-diethyl-0-2,4-dichlorophenylthiophosphate (DICHLOR~ENTHION) - 0-2,4-dichlorophenyl-0-methylisopropylamidothiophosphate 0,0-diethyl-0-2,5-dichloro-4-bromophenylthiophospllate (BROMOP~lOS-ETI~L) - dimethyl-p-(methylthio)phenylphosphate O,O-dimethyl-O-p-sulphamidophenylthiophosphate _9 _ ; ~
~ ., . _ _ _.. _ . _- ..... , .. . _ . _.. _ _. . _.. . .. .... . . ... ...... ....... ...... ......... ..
~(~474S9 O-~p- (p-chlorophel~y'l)-azophenyl~O,O d:imel,lly].thi,opllosphate (AY~OTI-IOI~TE ) O-et~llyl--S -4-chlorophenyl-ethylditlliopl~ospllate O-isol~u~yl-S-p-clllorophenyl-ethylditlli.opllosplla~e O,O dimethyl-S-p-chloropllenyl~hiophosphaLe :~
O,O-dimethyl-S-(p-chlorophenyl~hiomethyl)d:ithiophospllate O,O-di.ethyl p-clllorophenylmercaptomethyl-dithiophosphate (CARP.OPHEI~OTIIION) O,O-die~hyl-S~p-chlorophenylthiome~hyl-thi.opllosphate :~' . ~ .
,: 10 O,O-dimethyl-S-(carbethoxy-phenylm2l::1lyl)dithiophosphate (PHE~lTHOATE) ` O,O-diethyl-S-(carbofluorethoxy~phenylmethyl)-ditlliophosphate :~ O,O-dimethyl S-carboisopropoxy-phenylmethyl)-dithiophosphate ; 0,0--diethyl-7-hydroxy-3,4-tetramethylene-coumarinyl-thiophos-phate (COUMITHOATE) 2-me~hoxy-4-H~1,3,2-benzodio~aphosphorin-2-sulphide 0,0-diethyl-0-(5-pllenyl-3-i.sooxazolyl)thiophosphate : 2-(diethoxyphosphinylimino)-4-methyl-1,3-dithiolane tris-(2~methyl-1-aziridinyl)-phosphine oxide (METEPA) S-(2-chloro-1-phthalimidoethyl)-0,0-diethyldi~hiophospllate N-hydroxynaphthalimido-diethylphosphate . dimethyl-3,5,6-trichloro-2-pyridylphosphate -. :
.. 0,0-dimethyl-0-(3,5,6-trichloro-2-pyridyl)thiophosphate S-2-(ethylsulphonyl)ethyl dimethylthiolphosphate (DIOXYDE~TON-S-METHYL) ., , :
., .
.. ,, .. _ .. , ., . ... , .. , .. .. , . . , .. _., ., _,,, , ., . .. , _.. _.. . ~ .. ... , .. ,.. , .. ,,, . , _,, . .. , .
... ...... :.. . ..... . . ... . . .
'i. dietllyl-s-2-(e~:hylsu~ inyl)eL:llyl di.th-i.opllosphate (O~I~LSULFOlON) l~is--O~O-di.e~llylthi.opllosphoric acid ankyclride (SULIOTEP) - di.methyl-1,3-di(carbomethoxy)-1-pro~en-2-yl-phosphate dimetllyl-(2,2,~- trichloro-l-butyroyloxyethyl)phosphate (BUTONATE) -~ 0,O~dimethyl-0-(2,2-dicllloro-1-methoxy-vinyl)phospllate bis-(dimethylamido)~luorpllosphate (DIMEFOX) 3,~-dichlorobenzyl-triphenylphosphoniumchloride .,' 10 dimethyl-N-met:hoxymet~hylcarbamoylmethyl-dil:lliophosphate (FORMOCARB~M) O,O-die~-hyl-O (2,2 dichloro-l-chloroe~hoxyvinyl)-pllosphate 0,0-dime~hyl-0-(2,2-dichloro-1-chloroetlloxyvinyl)-phosphate O-ethyl-S,S-diphenyldithiolphosphate O-ethyl-S-benzyl-phenyldithiophosphonate 0,0 diethyl-S-benzyl-thiolphospllate ' ' ', 0,0-dimethyl-S-(4-ehlorophenylthiomethyl)dithiophosphate (METI-~LCARBOPHENOTHION) . O,O-dimethyl-S-(ethylthiomethyl)dithiophosphate diisopropylaminofluorophosphate (MIPAFOX) O,O-dimethyl-S-(morpholinylcarbamoylmethyl)dithiophosphate (MORPIIOTHION) bismethylamido-phenylphosphate O,O-dimethyl-S~(benzenesulphonyl)dithiophosphate 2~ . O,O-dimethyl-(S and O)-ethylsulphinylethylthiophosphate .
- 11 - - .
`~ ~047~ss 0,0-diethyl-0-4 nit~ophenylphospllat~e triethoxy--isopropoxy-bis(thiophospllirlyl)disulpllide 2-me~hoxy-4H-1,3,2-benzodio~aphosphorin-2 oxide octamethylpyrophosphoramide (SC~ ~ DAN) bis-(dimcthoxy~hiophosphinylsulphido)-phenylmethane N,N,N',N'-tetrame~hyldiamidofluorophosphate (DIMEFOX) O-phenyl O-p nitrophenyl-me~hanethlophosphonate (COJ~.P) O-methyl-0-(2-chloro-4-tert butyl-phenyl)-N-methylamidothio-phosphate (~ARL~NE) 0-ethyl-0-(2,4-dichlorophenyl)-phenylthiophosphonate 0,0-diethyl-0-(4-me~hylmercapto-3,5-dimethylphenyl)-thiophos-, phate .. . .. .
4,4'-bis-(0~0-dime~hylthiophosphoryloxy)-diphenyl disulphide 0,0-di-(B-chloroethyl)-0-(3-chloro-4-methyl-coumarinyl-7)-.. ,.................................................................... .:
` 15 phosphate ;v S-(l-phthalimidoethyl)-O,O-diethyldithiophosphate ~- 0,0-dimethyl-0-(3-chloro-4-diethylsulphamylphenyl)-thiophosphate O-methyl-0-(2-carbisopropoxyphenyl)-amidothiophosphate 5-(0,0-dimethylphosphoryl)-6-chloro-bicyclo(3 2,0)-heptadiene(1,5) 0-methyl-0-(2-i-propoxycarbonyl-1-methylvinyl)-ethylamido-thiophosphate. ~ -Nitro~henols and derivatives .. . .
.
4,6-dinitro-6-methylphenol, sodium salt [Dinitrocresol]
dinitrobutylphenol-(2,2',2")-triethanolamine salt 2-cyclohexyl-4,6-dinitrophenyl ~Dinex~
,. , ' . . .
.
. , ................. , . . : .. ~
,,' . .
2-1-methylhep~yl)-4,6--dinitrophenyl-cro~onate [~i.nocap]
2-sec.buty]--4,6-dinitrophenyl-3-mle~hyl butenoate ~inapacryl3 2-sec,b~ltyl-4,6-dini.trophenyl-cycloprop~.onate 2~sec.butyl-4$6-dinitrophenylisopropylca-rbonate [~inobuton]
, 5 ~liscellaneous f,~ pyrethrin::I
s pyreth-rin II
3-allyl-2 methyl-4-oxo-2-cyclopcntan-1--yl-chrysanthemumate (A l le tllrin)
.~,. O-ethyl-S-pllenyl-ethyldithiopllosphate ,. 0,0-dimethyl-0-(a-1nethylbenzyl-3-hydroxycrotonyl)phosphate . 10 2-chloro-1-(2,4 dichlorophenyl)vinyl-diet:hylpllosphate . (CI~LORFE:NVINPIIOS) ..
i l-chloro-1--(2,4,5-trichlorophenyl)vinyl-dimethylphosphate 0-~2-chloro-1-(2,5-dichlorophenyl)]vinyl-O,O-diethylthio-phosphate .;i 15 Phenylglyoxylonitriloxime-O,O-diethylthiophosphate (PHOXIM) i::! O,O-diethyl-O-(3-chloro-4-methyl-2-oxo-2-H-l-benzopyran-7-yl)-. thiophosphate (COUMAPHOS) 2,3-p-dioxandithiol-S~S-bis(O,O-diethyldithiophosphate) ~.
(DIOX~THION) 5-[(6-chloro-2-oxo-3-benzoxazolinyl)methyl]O,O-diethyldithio-phosph~te (PIIOSALONE) 2~(diethoxyphosphinylimino)-1,3-dithiolane . - O,O-dimethyl-S-[2-methoxy-1,3,4-thiadiazol-5-(4H)-onyl-(4)-- methyl]dithiophosphate Z5 O,O-dimethyl-9-phthalimidomethyl-dithiopllosphate (IMIDAN) ~ . , _ 7 _ ,~
, . i ,.
.-- . .
47~89 O~o-diet~ o~(3~5~6-l~r:i-chloro-2-py~-idyl)l~hio~ os~ at:e O,O-di.e~hyl O-~-pyra~inyl~hiophosplla~e (THION~ZIN) ~' 0,O~dic~hyl-0-(2-isopropyl-4-me~hyl-6-pyriT:liclyl)t:hiophosphate (DIA~XNON) 0,0-di.ethyl-0-(2-quinoxalyl)thiophosphatè
0,0-dimethyl-S-~4-oxo-1,~,3-benzotria~in~3(4I-I)-ylTnethyl)-dithiophospllate (A%INPI~OS~THYL) 0,0-dicthyl-S-(4-oY~o-1,2,3-benzotriazin-3(~II)-ylmethyl)- -dithiophosphate (AZINPHOSETllYL) S [(4,6-diamino-s triazill-2-yl)rnethyl]-0,0-dimethyldit:hio-. phosphate (ME.NAZON) .;
j' O,O-dimethyl-O (3-chloro-4-nitrophenyl)thiophosplate ` (CllLORTlIION) '' O,O-dimethyl-O(or S)-2-(etllylthioethyl)thiophosl)hate 15 (DE~ETON-S-METHYL) 2~(0~0-dimethyl-phosphoryl-thiomethyl)-5-methoxy-pyrone- --4-3,4-dichloroben~yl-triphenylphosphoniumchloride :.
0,0-diet:hyl-S-(2,5-dichlorophenylthiomethyl)dithiophosphate ' ~-' .
(PHENKAPTON) . :. .
0,0-diethyl-0-(4-methyl-cumarinyl-7`-~hiophosphate (POTASAN) $-amino bis(dimethylami~o)phosphinyl-3-phenyl-1,2,4-triazole (TRI~MIP~IOS) N-methyl-5-(0,0-dimethylthiolphosphoryl)-3-thiavaleramide ~VAMIDOTHION) 0,0-diethyl-0-12-dimethylamino-4-methylpyrimidyl-(6)]-thio- .
phosphate (DIOCTHYL) ; . .. .
, .
' , ,.. ,, ., --.. ....... .
.
- ~47489 O, O - di.methy].-S - (methy] carbalnoy1me l:hyl) - 1 hi.ophospllat:e (O`IETI~Ol~TE) i~ O -~thy1-0 - (8- quino:l i.nyl) -plleny1t~ iophosr)llonatc! (OXINOTIIIOPIIO.S) O~ etllyl-S~Illethyl--ar~ lothiophosphate (I:~ONITOR) O-methyl-O- (2,5-dichloro--4-bromoplleny:l.)-bellzoth;.ophosphate ` 5 (~IIOSVEL) O,O,O~O-tetrapropyldithiophospha~e 3-(dimethoxyphosphlnyloxy)-N-methyl-N-methoxy-cis-crotonarnide O,O--dimethyl-S-(N-ethylcarbamoylmethyl)ditlliopllosphate (ETI-lOATE-~lETHYL) O,O-diethyl-S-(N-isopropylcarbamoylme~hyl)-di.thiophos~ ate (l'ROTllOATE) S-N--(l-cyano-l-methylethyl)carbalnoylmetllylcliethyl~hiolphosplla~e (cyANTlloATE:) S-(2-acetamidoethyl)-0,0-dimethyldithiophosphate - ~-~lexamethylphosphoric acid triamide (llE~fPA) 0,0-dimethyl-O-(2-chloro-4-nitrophenyl,)thi.ophosphate (DICAPTHON) O,O-dimethyl-O-p-cyanophenyl thiophosphate (CYANOX) O-ethyl-O-p-cyanophenylthiophosphonate 0,0-diethyl-0-2,4-dichlorophenylthiophosphate (DICHLOR~ENTHION) - 0-2,4-dichlorophenyl-0-methylisopropylamidothiophosphate 0,0-diethyl-0-2,5-dichloro-4-bromophenylthiophospllate (BROMOP~lOS-ETI~L) - dimethyl-p-(methylthio)phenylphosphate O,O-dimethyl-O-p-sulphamidophenylthiophosphate _9 _ ; ~
~ ., . _ _ _.. _ . _- ..... , .. . _ . _.. _ _. . _.. . .. .... . . ... ...... ....... ...... ......... ..
~(~474S9 O-~p- (p-chlorophel~y'l)-azophenyl~O,O d:imel,lly].thi,opllosphate (AY~OTI-IOI~TE ) O-et~llyl--S -4-chlorophenyl-ethylditlliopl~ospllate O-isol~u~yl-S-p-clllorophenyl-ethylditlli.opllosplla~e O,O dimethyl-S-p-chloropllenyl~hiophosphaLe :~
O,O-dimethyl-S-(p-chlorophenyl~hiomethyl)d:ithiophospllate O,O-di.ethyl p-clllorophenylmercaptomethyl-dithiophosphate (CARP.OPHEI~OTIIION) O,O-die~hyl-S~p-chlorophenylthiome~hyl-thi.opllosphate :~' . ~ .
,: 10 O,O-dimethyl-S-(carbethoxy-phenylm2l::1lyl)dithiophosphate (PHE~lTHOATE) ` O,O-diethyl-S-(carbofluorethoxy~phenylmethyl)-ditlliophosphate :~ O,O-dimethyl S-carboisopropoxy-phenylmethyl)-dithiophosphate ; 0,0--diethyl-7-hydroxy-3,4-tetramethylene-coumarinyl-thiophos-phate (COUMITHOATE) 2-me~hoxy-4-H~1,3,2-benzodio~aphosphorin-2-sulphide 0,0-diethyl-0-(5-pllenyl-3-i.sooxazolyl)thiophosphate : 2-(diethoxyphosphinylimino)-4-methyl-1,3-dithiolane tris-(2~methyl-1-aziridinyl)-phosphine oxide (METEPA) S-(2-chloro-1-phthalimidoethyl)-0,0-diethyldi~hiophospllate N-hydroxynaphthalimido-diethylphosphate . dimethyl-3,5,6-trichloro-2-pyridylphosphate -. :
.. 0,0-dimethyl-0-(3,5,6-trichloro-2-pyridyl)thiophosphate S-2-(ethylsulphonyl)ethyl dimethylthiolphosphate (DIOXYDE~TON-S-METHYL) ., , :
., .
.. ,, .. _ .. , ., . ... , .. , .. .. , . . , .. _., ., _,,, , ., . .. , _.. _.. . ~ .. ... , .. ,.. , .. ,,, . , _,, . .. , .
... ...... :.. . ..... . . ... . . .
'i. dietllyl-s-2-(e~:hylsu~ inyl)eL:llyl di.th-i.opllosphate (O~I~LSULFOlON) l~is--O~O-di.e~llylthi.opllosphoric acid ankyclride (SULIOTEP) - di.methyl-1,3-di(carbomethoxy)-1-pro~en-2-yl-phosphate dimetllyl-(2,2,~- trichloro-l-butyroyloxyethyl)phosphate (BUTONATE) -~ 0,O~dimethyl-0-(2,2-dicllloro-1-methoxy-vinyl)phospllate bis-(dimethylamido)~luorpllosphate (DIMEFOX) 3,~-dichlorobenzyl-triphenylphosphoniumchloride .,' 10 dimethyl-N-met:hoxymet~hylcarbamoylmethyl-dil:lliophosphate (FORMOCARB~M) O,O-die~-hyl-O (2,2 dichloro-l-chloroe~hoxyvinyl)-pllosphate 0,0-dime~hyl-0-(2,2-dichloro-1-chloroetlloxyvinyl)-phosphate O-ethyl-S,S-diphenyldithiolphosphate O-ethyl-S-benzyl-phenyldithiophosphonate 0,0 diethyl-S-benzyl-thiolphospllate ' ' ', 0,0-dimethyl-S-(4-ehlorophenylthiomethyl)dithiophosphate (METI-~LCARBOPHENOTHION) . O,O-dimethyl-S-(ethylthiomethyl)dithiophosphate diisopropylaminofluorophosphate (MIPAFOX) O,O-dimethyl-S-(morpholinylcarbamoylmethyl)dithiophosphate (MORPIIOTHION) bismethylamido-phenylphosphate O,O-dimethyl-S~(benzenesulphonyl)dithiophosphate 2~ . O,O-dimethyl-(S and O)-ethylsulphinylethylthiophosphate .
- 11 - - .
`~ ~047~ss 0,0-diethyl-0-4 nit~ophenylphospllat~e triethoxy--isopropoxy-bis(thiophospllirlyl)disulpllide 2-me~hoxy-4H-1,3,2-benzodio~aphosphorin-2 oxide octamethylpyrophosphoramide (SC~ ~ DAN) bis-(dimcthoxy~hiophosphinylsulphido)-phenylmethane N,N,N',N'-tetrame~hyldiamidofluorophosphate (DIMEFOX) O-phenyl O-p nitrophenyl-me~hanethlophosphonate (COJ~.P) O-methyl-0-(2-chloro-4-tert butyl-phenyl)-N-methylamidothio-phosphate (~ARL~NE) 0-ethyl-0-(2,4-dichlorophenyl)-phenylthiophosphonate 0,0-diethyl-0-(4-me~hylmercapto-3,5-dimethylphenyl)-thiophos-, phate .. . .. .
4,4'-bis-(0~0-dime~hylthiophosphoryloxy)-diphenyl disulphide 0,0-di-(B-chloroethyl)-0-(3-chloro-4-methyl-coumarinyl-7)-.. ,.................................................................... .:
` 15 phosphate ;v S-(l-phthalimidoethyl)-O,O-diethyldithiophosphate ~- 0,0-dimethyl-0-(3-chloro-4-diethylsulphamylphenyl)-thiophosphate O-methyl-0-(2-carbisopropoxyphenyl)-amidothiophosphate 5-(0,0-dimethylphosphoryl)-6-chloro-bicyclo(3 2,0)-heptadiene(1,5) 0-methyl-0-(2-i-propoxycarbonyl-1-methylvinyl)-ethylamido-thiophosphate. ~ -Nitro~henols and derivatives .. . .
.
4,6-dinitro-6-methylphenol, sodium salt [Dinitrocresol]
dinitrobutylphenol-(2,2',2")-triethanolamine salt 2-cyclohexyl-4,6-dinitrophenyl ~Dinex~
,. , ' . . .
.
. , ................. , . . : .. ~
,,' . .
2-1-methylhep~yl)-4,6--dinitrophenyl-cro~onate [~i.nocap]
2-sec.buty]--4,6-dinitrophenyl-3-mle~hyl butenoate ~inapacryl3 2-sec,b~ltyl-4,6-dini.trophenyl-cycloprop~.onate 2~sec.butyl-4$6-dinitrophenylisopropylca-rbonate [~inobuton]
, 5 ~liscellaneous f,~ pyrethrin::I
s pyreth-rin II
3-allyl-2 methyl-4-oxo-2-cyclopcntan-1--yl-chrysanthemumate (A l le tllrin)
6-chloropiperonyl-chrysanthemuma~e (Bartllrin) ~ 2,4-dimethylbenzyl-chrysanthemumate (Dimethrin) ,, 2,3,4,5-tetrahydrophthalimidome'l:hylcllrysanthemumate 4-chlorobenzyl-4-chlorophenylsulphide [Chlorobensid]
- ~
r, ' 6-methyl-2-oxo-1,3-dithiolo-[4,5-b]-quinoxaline (Quino- -~: 15 methi.onate~ -'!: (I)-3~(2-furfuryl)-2-methyl-4-oxocyclopent-2-enyl(I)-(cis-~
trans)-chrysanthemum-monocarboxylate ~Furethrin3 2-pivaloyl-inclane-1,3 dione [Pindon]
4-chlorobenzyl-4-fluorophenyl-sulphide [Fluorobenside]
5,6-dichloro-1-phenoxycarbamyl-2-trifluoromethyl-benzimidazole [Fenozaflor]
p-chlorophenyl-p-chlorobenzenesulphonate [Ovex]
p-chlorophenyl-benzenesulphonate [Fenson]
~047489 p-chlorop'lenyl-2,4,5 trich].orophenyl.st~ 0ne [Tcl:radi:Eon~
p- clllorophenyl-2,4,5-trichlo~o~ ylsull)hj-.1e ~JTel~rasul~
p - ch] oroben~l p - chlorophenyl sulphicle [ Ch:l orobens i de ]
2 - thio ~l , 3--dithiolo- (5, 6) -qulnoxaline [Thiochinox ]
prop-2-ynyl-(4-t-butylphenoxy)-cyclohe~ylsulphite [Propargil].
l~ormam;.dines ~, , . _ .
l-dimechyl-2- (2 ' -met:hyl-4' -chlorophenyl) -formamidine (CELC~ODIM~
l-metl-yl-2-(2' methyl-4~-chlorophenyl)-~ormc.midi.ne 1-methyl-2- (2 ' -methyl-4' -bromophenyl) -~ormamidine l-methyl-2 - (2 ', 4 ' -dime thylphenyl ) - formamidine l-n-butyl-l-methyl-2- (2 ' -me~hyl -4' -chloro~henyl) -Eormamidine l~methyl-l- (2 ' -methyl-4' -chloroaniline-met:llylene)-~ormarnidi.ne 2- (2"-methyl-4"-chlorophenyl-formamidine :~
l-n butyl-2- (2 ' -methyl-4' -chlorophenyl-imino) -pyrolidine Urea N-2-methyl-4-chlorophenyl-N' ,N' -dimethyl-thiourea Carbamates l~naphthyl-N-methylcarbamate (CARBARYL) .: .
2--butinyl-4-chlorophenylcarbamate 4-dimethylamino-3,5-xylyl-N-methylcarbarllate - 4-dimethylamino-3-tolyl-N-methylcarbamate (AMINOCARB) 4-methylthio-3,5-xylyl-N-methylcarbamat:e (ME:T~IIOCAP~B) 3,4,5-trimethylphenyl-N-methylcarbamate 2-chlorophenyl-N-methylcarbamate (CPMC) . , , , . ' ' ' , .' ' " .
:; ~
~047 ~; 5 cllloro-G-o;o~2-no~borarle carbonitrile~O~ etllylcarbamoyl)~
~ -,, .
. oxime ,", 1-(dime~ $~1c~ba}noyl-5~me~1lyl 3-pyra~:olyl~N,N-dimetllylcarba mate (DI~ETILA~l) 2,3-dihydro-2,2-dimethyl-7-benzofuLanyl-N-metllylcarbamate , (CARBOFUR~N) ,,.', 2-methyl-2-me~hylthio-propionaldehyde-0-(metllylcarbamoyl)-ox:Lme (ALDICARB) ;~: 8-quinaldyl-N-methylcarbamate and its salts.
methyl-2-isopropyl-4-(methylcarbamoyloxy)carbanilate m-(l-ethylpropyl)phenyl-N-methylcarbamate 3,5-di-tert.butyl--N-methylcarbamate m-(l methylbutyl)pllenyl-N-methylcarbamate 2~isopropylphenyl-N-methylcarbamate ;. 15 2-sec.butylphenyl-N-methylc2rbamate :, ~ m-tolyl-N- methylcarbamate , -2,3-xylyl-N-methylcarbamate 3-isopropylphenyl-N-methylcarbamate 3-tert.butylphenyl-N-methylcarbamate . 20 3-sec.butylphenyl-N-methylcarbamate ; . 3-isopropyl-5-methylphenyl-N-methylcarbamate (PRO~EC~RB) 3,5-diisopropylphenyl-N-methylcarbamate - 2-chloro-5-isopropylphenyl-N-methylcarbama~e 2-chloro-4,5-dimethylphenyl-N-methylcarbamate 2-(1,3-dioxolan-2-yl)phenyl-N-methylcarbamate (DIOXACARB) ~` ~047~89 :
,S-dir.letl~ .-1,3-dioxolan-2-yl)-pllenyl~ net:hylcarbamate 2-(1,3-dioi~olan~~-yl)pllenyl-N,~I-dimetllylc~rbam~te 2-(1,3-di ~.hiolan-2-yl) N,N-di.methylcarbamat:e 2-(1,3-dith;olan-2-yl)phenyl-N,N-clim~tllylcarlamate , - 5 2-isopropoxyphenyl-N-me~hylcarbamate (APROC~B) 2-(2-prop;nyloxy)phenyl-N-methylcarbarnate 3-(2--propinyloxy)phenyl-N-me,llylcarbamate 2-dimetllylaminophenyl-N-methy:lcarbamate -~
2-diallylaminophenyl-N-met:hylcarbamate ~-~-di.allylamino-3,5-xylyl-N-methylcar~am2te (ALL~'XICARB) 4-benæothienyl-N-methylcarbamate 2,3-dihydro--2-me~llyl-7-ben~o~uranyl-N--methy].carbamate : 3-methyl-1-phenylpyrazol-5-yl-N,N-di.methylcarbamate l-isopropyl-3-methylpyrazol-~-yl-N,N dimethylcarl~amate (ISO~N) 2-dimethylclmino-5,6-dimethylpyrimidin-4-yl-N,N-dimethyl-carbamate3-methyl~-dimethylaminomethyleneiminophenyl N-methyl-carbamate 3,4-dimethylphenyl-N-methylcarbamate 2-cyclopentylphe~-N-methylcarbamate 3-dimethylamino-metllyleneiminophenyl-N-methylcarbamate (FO~METANATE) and its salts ~ :
l-methylthio-ethylimino-N-methylcarbamate (METHOMYL) 2-methylcarbamoyloximino-1,3-dithiolane .~ -5-methyl-2-methylcarbamoyloximino-1,3-oxythiolane ' ~
' ~0474ss 2 (1-me~hoxy-2 propo,~y)ph~nyl~ -tne~hylcarbaMate 2~ utin-3-yl-o~)phenyl-N-~l~e~llylca~l~aMa~e :1. c1i.metl~yl.carbamyl-l-me~ y].t:llio-O-me~h,71carhalrlyl-formoxime 1-(2~-cyanoethylthio)-0-methylcarbamyl-acetaldo~f.lme ]-methylthio-0-carbamyl~acetalcloxime 0-(3-sec.butylphenyl)-N-pllenyltllio~N-methylcarballJate 2,5-dime~hyl-1,3~dithiolane-2-(0 methylcarbarnyl)-aldoxime) 0-2-diphenyl-2~-metllylcarbamate ~` 2-(~-methylcarbamyl-oximino)~3-chloro-bicyc~o[2.2,1]lleptane 2-(N-me~hylcarbamyl-oximino)-bicyclo[2.2,1]heptane 3-isopropylphenyl-N-methyl-N-cllloroacetal-carbamate 3-isopropylphenyl-N-mcthyl-~-methy].thiome~hyl-ca-rbamate '~
.~ 0-(2,2-dimethyl-4-chloro-2,3-dihydro-7-benzofuranyl)-N-methyl-. .
carbamate 0-(2,2,4-trimethyl-2,3-dihydro-7-benzofuranyl)-N-methylcarba-rnate 0-naphthyl-N-methyl-N-acetal-carbamate 0-5,6,7,~-tetrahydronaphthyl-N-methyl-carbamate 3-isopropyl-4-methylthio-phenyl-N-methylcarbamate 3,5-dimethyl~4-methoxy-phenyl-~-methylcarbamate 3-methoxymethoxy-phenyl-N-metllylcal-bamate 3-allyloxyphenyl-N-methylcarbamate 2-propargyloxymethoxy-phenyl-N-methyl-carbamate 2-allyloxyphenyl-N-methyl-carbamate 4-methoxycarbonylamino-3-isopropylphenyl-N-methyl-carbamate 3,5-d;rn~l Hy~ metl~c)x~Jcarbollylamino-pheny-l-N-methyl-carbama~e ~-y-me~l-y~ iol~o~y~ eny]~ nethyl- ca~ a~ -3-(a-netlloxym~thyl-2-propeilyl)-phenyl~N-methyl-carbamate 2 chloro-5-tert.-butyl-phcny]-N-metllyl-carbamate 4~(methyl-propargylamino 3,5-xyly].~N--methyl-carbamate 4-(methyl-y-cl-lloroallylalllino)-3,5-~ylyl-N--met:hyl-carbamate 4-(methy]-~-chloroallylamino)-3,5-xylyl-N-methyl-ca]^bamate l-(~-ethoYyca~:bonylethyl) 3-methyl-5-pyrazolyl-N,N-dimethyl-carbamate ; 10 3- methyl-4 (dimethylamino-methylmercapto-methyleneimino)-phenyl-N methyl-carbamate 1,3-bis(carbamoylthio)-2-(N,N-dimethylamino)-propanehydro-:, chloride 5,5-dimethylhydroresorcinoldimethylcarbamate 2-[ethyl-propargylamino]-phenyl.-N-methylcarbamate .` 2-[methyl-propargylamino]-phenyl-N-methylcarbamate ~ 4-[dipropargylamino]-3-tolyl-N-methylcarbama~e '< 4-[dipropargylamino]-3,5-xylyl-N-methylcarbamal:e ~ '.
! 2-~allyl-isopropylamino]-phenyl-N-methylcarbamate 3-[allyl-isopropylamino]-phenyl-N-methylcarbamate ; Chlorinated Hydrocarbons y-hexachlorocyclohexane [GAMMEXANE; LINDAN; y HCH]
~., 1,2,4,5,6,7,8,8-octachloro-3a,4,7,7a -tetrahydro-4,7-- methylene indane ~CHLORDAN]
1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-.
. . .
, methylene indane 1,2,3,4,10,10-hexachloro-1,4,4~,5,8,8~-hexahydro-endo-1,4-exo-5,8-dimethano-naphthalene 1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4~,5,6,7,8,8~-octahydro-exo-1,4-endo-5,8-dimethanonaphthalene 1,2,3,4,10,10-hexachloro-5,7-epoxy-1,4,4~,5,6,7,8,8~-octahydro-endo-endo-5,8-dimethanonaphthalene.
: The compounds of the formula I are also suitable for combatting plant pathogenic nematodes.
: 10 The compounds of the formula I may be used as pure active sub-stance or together with suitable carriers and/or additives. Suitable - carriers and additives can be solid or liquid and correspond to the sub-stances conventionally used ,~
;' .~
,, h -19-~0~7489 in formula~ioI2 tccllnique such, fo~ e~ample, as solvcnts, <lispersclllts, ~e~ g agel-lts, a~lllesives, tllickeners~ binders and/o-r fcl^tilisers.
For application, the compounds of the forrnula I may ; 5 be processed to dusts, emulsion concentrates, granllles, dis~
persions, sprays, to solu~ions, or suspensions, in the con-- ventiona] form-llation which is co~nonly en-ployed in app]i cation technology ~lention may al~so be made o~ cattle dips and spray races, in which aqueous preparations are used.
-~ 10 The agents according to the invention àre manuac-tùred in lcnown manner by intimately mixing and/or grinding active sul~stances of the for~ula I with the suitable carriers, optionally with the addition of dispersants or solvents WlliCIl are inert towards the active substances. The active subs~ances may take, and be used in, the following forms:
Solid forms:
Dusts, tracking agents, granules, coa~ed granules, impre~nated granules and homogeneous granules.
Liquid forms: i a) active substances which are dispersible in water:
wettable powders, pasts, emulsions; ~ ;
b) solutions.
To manufacture solid forms (dusts, tracking agents), the active substances are mixed with solid carriers. Suit-able carriers are, for example: kaolin, talcum, bolus, loess, , . . .
~)47489 chalk, limes~one, ground limes~olle, a~ac]ay, dolomite, ;-diatomacec)us ea-rth, precipita~cd silica, alkaline earth sili.cates, sodium and potassium alumin:ium silica~e~s (feld-spar and mica), calcium~d inagnesium su]phates, magnesium : 5 o~ide, ground synthetic materials, fertilisers, ~or example `-- ammonium sulphate, ammonium phosphate, ammonium ni~rate, : urea, ground vegetable products, such as corn meal, bark .:
dust, sawdust~ nutshell meal, cellulose powcler, residues o plant extract:ions, activated charcoal etc These substances can either be used singly or in admixture ~ith one another.
:- Granules can be very eas:lly manufactured by dissol-ving an active substance of the formula I in an o~ganic solvent and applying the resul~ing solution to a granulated material, for example attapulgi~e, SI02, granicalcium, belltonite etc and then evaporating the solvent.
Polymer granules can also be manuf~c~ured by mixin;, ; the active substances of the formula I with pol~erisable compounds (urea/formaldehyde; dicyandi2mide/formaldehyde;
melami.ne/formaldehyde or others), whereupon a mild polyn~eri-sation is carried out that does not affect the active substances and in the process of which the granulation is carried out during the gel formation It is more advantageous to impregnate finished, porous polymer granules (urea/
formaldehyde, polyacrylonitrile, polyester or others) ~Jhich have a specifi.c surface area and a favourable predeterminablF:
n47~8 : " ' - adsorption/desorption ratio, with the ac~ive substances, ~or example in th~ orm of th~ir solutions (in a lo~ boiling solvent) and to remove ~he solvent. Polymer granules of this kind in the ~o~m of microgranules having a bulk density of ~, ....
- 5 300 g/liter to 600 g/liter can also be manu~actured ~ith the aid of atomisers. The dusting can be carried out from aircrat .~ :
over extensive areas of cultures of useful plants.
. . It is also possible to obtain granules by compacting ~ .
.. the carrier ~ith the active substan.ce and carriers and subsc-- 10 quently com~linu~ing the product.
To tllese mixtures can also be a.dded additives which ;. stabi.lise the active substance and/or non-ionic, anioni.c arld ~., .
. cationic sur~ace active substances, whicll, for example, improve the adhesion of the active ingredients on plants or parts o plants (adhesives and agglutinants) and/or ensure a better wettability (wetting agents) and dispersibility (dispersirg agents). Examples of suitable adhesives are the following: olein/chalk mixture, cellulose derivatives (methyl ::
cellulose, carboxymethyl cellulose), hydroxyethyl g]ycol - .
: 20 . ethers o monoalkyl and diallcyl phenols having 5 to 15 ethylene ox;de radicals per molecule and 8 to 9 carbon atoms ; in the alkyl radical, lignin sulphonic acids, their alkali metal and alkaline earth metal salts, polyethylene glycol ethers (carbowaxes), ~atty alcohol polyethylene glycol ethe~s having 5 to 20 ethylene oxide radicals per molecule and 8 to . .
.. . .. .. .. .. .. ..
ln47489 . .
18 carbon atoms in thc atty a]cohol moiety, condensation produc~s o~ e~hylene oxide/propylcne oY~ide, polyvinyl pyrro-lidones, polyvinyl alcohols, con~ensation products of urea and ormaldehyde, and also late~ products.
The ~ater-dispersible concentratcs of the active substance, i.e. ~ettable po~ders, pastes and emulsiiable concentra~es, are agents whicll can be diluted wi~l-l water to . . , ~ any concentra~ion desirecl. They consist of active substance, .... .
~ carrier, opti~nally additives which stabilise the active - 10 substance, sur~ace-active sùbstance and anti-foam agents ; and, optionally,solvents.
. .
l~ettable powders and pastes are ob~ained by ml~ g and grinding the active substances with dispersing agents and ~ulverulent c~rriers in suitable apparat-us un~il homogeneity is attained. Suitable carriers are, for exam.ple, those men-tioned for the solid forms of application. In some cases it is advantageous to use mixtures of dif~erent carriers. As dispersing agents there can be used, for example, condensation products o~ sulphonated naphthalene and sulphonated naphtha lene derivatives with formaldehyde, condensation products o~
naphthalene or naphthalene sulphonic acids with phenol and formaldellyde, as well as-alkali, ammonium and alkaline earth me~al salts of lignin sulphonic acid, in addition, allcylaryl ~ sulphonates, alkali and alkaline earth metal salts o~ dibutyl : 25 naphthalene sulphonic acid, fatty alcohol sulphates such as .~,, , ,,, ,, ,., ,. , . , ., _ .
' ~
-` ~0474t39 ~:
salts of sulpllated hexadecanols, heptadecanols, octadecanols, and salts o suli~ha~ed ~atty alcol~ol glyco] e~hers, the sodiurll salt o~ oleoyl e~hionate, t}-le soclium salts o oleoyl methyl taurid~, ditertiary acetylene glyco]s, dialkyl di-~`~ 5 lauryl a~nonium chloride and fa~ty acid alkali and alkaline earth metal salts.
Suitable anti-fo~m agents are silicones.
The active substances are mixed~ gro~md, sieved and strained ~ith the additives cited hereinabove, in such a manner that, the size of the solid particles does not exceed 0 02 to 0,04~in wettable po~ders, and 0.03~ in past-es.
i To produce emulsifiable concentrat~es and pastes, dispersing .~ agents such as those cited above, organic solvents, and water are used. Examples of suitable solvents are: a]cohols, benzene, xylene, toluene, dimethyl sulphoxide, and mineral oil fractions which boil between 120 and 350C. The solvents must be ~
pract-ically odour]ess, not phytotoxic, and inert to the active -substances.
Furthermore, the agents accor~ing to the invention 20 can be applied in the form of solutions. For this purpose -~
: . :
v the active substances, or several ac~ive substances of the `
general ormulà X, are dissolved in sui~ab]e organic solvents, mixtures of solvents or in water Aliphatic and aromatic h~r~ ~-drocarbons, chlorinated derivatives thereof, alkyl naphthalene~
25 and mineral oils, singly or in admixture wi~h each other, can ,... .
J
.
' " .. .... ... . .... .... .... . ... .. . .. . . . . .
, . . .
. .
`;~ 1(~4~ 9 .. ~ .
43.~ parts of xylene.
~- b) 25 parts of active s~lbstance, ;- 2 5 parts of epoxidised vegetable oil, parts of an alkyl.arylsulphonate/fatty alcohol--polyglycol ether m:i~ture, . 5 parts o dimethylforrllamide, . 57.5 parts of xylene.
~` . From ~hese concentra~es i~ is possible to pro~lce, by dilution ~.7:ith ~.7ater, emulsions o any desired concentra tion.
- Spray:
The ~ollowing constituents are used to prepare a 5% spray:
: 5 parts of active subs~:ance, .. 15 1 part of epichlorohydrin, 94 parts of benzine (boiling limits 160~ - 190C).
~ ' ~
,, .
., ' , ~
,, ''"
'~ ' .
. .
- ~ , .
, 1.7 parts of Chami~agn~ chalk/hydroxyethyl cellulose : mi~ture (1:1), ~-J '~ ~. 3 parts of sodium aluminium silicate, lG.5 parts of kieselguhr, 46 parts of kaolin d)10 parts o active substance, 3 par~s of a mix~ure of the sodium salts of :~ saturated fatty alcohol sulphates, : ..... .
~:: 5 parts of naphthalenesulpllonlc acid/~ormaldehyde ~ "
condensate, 82 parts o kaolin.
- ~ The active substances are intimately mixed, in suit-able Ir~ixers, with the additives, the mixture being then ground ~;.: ~ - .
, in tlle appropriat-e mills and rollers. Wettable po~ders are :: 15 ob~ai.ned which can be diluted ~7ith ~Jater to give suspensions ... .
- of any desired concentration.
.~. .
~;' mul ial~ e concentrates:
i.l .
.. The ollo~ing substances are used to produce a) a 10% and b) a 25% emulsifiable concentrate:
a) 10 parts o active subs~ance, A l3.4 parts of epoxidised vegetable oil~
13.4 parts of a combination emulsifier consisting - of fatty alcohol polyglycol e~her and alkyl-arylsulphonate calcium salt, " .
s 25 bO parts of dimethylformamide, ,,"
- 26 _ .. .. . ... . ..... ... ... ... ... . ....... . . ... . .... .. .. .... . .. ... . .. . ....... . .. . .. .. . . . . ..
,; . . - : ~ . - ., , ' ' ''. ~
9~89 3 . SO parts of polyethylelle glycol, 91 par~s of l~aoliII (particle size 0.3 - 0.8 mm).
The active substance is mixed witll epichlorohydrin : and dissolved wltll 6 parts of ace~olle; the polyethy]ene .
glycol alld cetyl polyglycol ethex are then adcled. The th~s ~:. o~tai.ned solution is sprayed on kaolin, and the ace~one - subsequellt].y e~raporated in vacuo.
I~ettable pow~er:
Th~ following constituen~s are used for the pre-10 paration of a) a 40%, b) and c) a 25%, and d) a 10% wettable T~Wder:
.~ a)40 par~s of active substance, , parts o sodium lignin sulphonate, 1 part of sodium dibu-~yl-naph~halene sulphonate, 54 par~s of silicic acid, .. ~ b) 25 parts of active substance, 4.5 parts of calcium lignin sulphona~e, 1.9 parts o Champagne chalk/hydroxyethyl cellulose . mixtuxe (1:1), 1.5 parts of sodium dibutyl naphthalene sulphonate, . . ~ .
. 19,5 parts of silicic acid, 19,5 parts of Champagne chalk, 28,1 parts of kaolin.
c)25 paxts of active substance, 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, ,, , :
. . .
_ 27 -.
~ ' ~
be used as organic solvents.
The content of active substallce in the above des-cribed agents is be~een 0. l~/o to 95%, in wllicll connection it should be ment.ioned that, in the case of application from ~-aircra~ or soMe other suitable means of application, it is possible to use concen~rations of up ~o 99.5% or even pure ac~ive substance. -The active substances o the fonllula I can, for example, be formulated as follows:
~ .
~ 10 Dusts :
The follo~Jing substances are used to manufacture a) ~ a 5% and b) a 2% dusc:
a)5 parts o active substance 95 parts of talcum - 15 b)2 parcs of active substance , 1 part of highly disperse silicic acid c 97 parts of talcum.
The active substances are mixed with the carriers and ground.
~,; 20 Granules ;~ The following substances are used to produce 5%
,ji granules:
- 5 parts of active substance, 0,25 parts of epichlorohydrin, - 25 0 25 parts of cetyl polyglyco] eLher~
.
, :
. ,.,.. ,,.. ,., . ,,.. ,.,.. . ,,.. ,, ,., .,. , . .. ,, .. , ~ .
~047489 - Example 1 : ~ S
At room temperature 10.1 g of 0-ethyl-~-(n)-propyl-thio~-~phosphoric chloride in 2~ ml of absolute ether are added dropwise to a solution of 11.6 g of 4-hydroxy-4'-chloro-azo benzene and 5.1 g of triethylamine in 150 ml of absolute ether.
The salt precipitate is filtered off and the mixture is treated with 200 ml of ice water with stirring. The organic phase is isolated, washed once with water and shaken twice with ice-cold "
~ 5% sodium hydroxide solution and then washed neutral with ,. .
. water. The ethereal phase is then treated with activated char-coalJ filtered, dried, and the solvent is evaporated. The resi-r: i , due is dried for 3 hours at 70C and 0.1 Torr to give the com-~; pound of the formula ,;
.. , O
` C1~3N=N~3 ~S) C ~I ( n ) , ................................................ . .
r~,' with a refractive index of n20 1.6185.
The following compounds are also manufacture in analogous manner:
, . . . .
.
: ~N=~o-~a3~l7(n~ nD20= 1,6142 ` ~
ri~ ~ O .. ' : .
-- ~==~ ~==\ 11 /OC2H
,- Cl ~ N=N ~ ~SC3H7(n) D - 1,6251 ''` ' ' .
, ~ .
-~
:.
. :
- 1047~39 `. S
Cl~N=I~-~ 11 <3CzH5 nD20 SC3H7(n) = 1,6345 . C 1 ,. I , O .::
C1~3N--N~ C3H7(n) nD20 _ 1, 6300 ,. o " CH3~~ `~ 3 7 ( ) nD2 = 1, 6132 :
C1~3-N=N~~,<OC E5 nD - 1, 6495 'i Cl S
~=~ ~c=~11 /OC H
~ ~ ~N=N~ 3 7 ( nD ~ 1, 6348 ;:' S
i~, CH~ ~N~3 3 7 ( ) n20 = 1, 6336 ..
~' O
11 ~OC H
~,~ ~N--N~o--P< 2 5 CH n2o ., - SCH2--CH< 3 D - 1, 6082 0~I3 Cl~3N-N~ ~<OC2H5 20 SCH2--CH<~3 nD = 1, 6078 ~" .
: . ' ~, ~
. , .
Example 2 1047~89 ~,, ' .
~ction against ticks .
~ A) Rhipicephalus bursa , . .
Five adult ticks and 50 tick larvae were counted into a glass tube and immersed for 1 to 2 minutes in 2 ml of an aqueous emulsion from an emulsion series each containing 100, ; 10, 1 and 0.1 ppm f test substance The tube was then sealed ~ . .
with a standardised cotton wool plug and placed on its head, so that the active substance emulsion could be adsorbed by the cotton wo~l.
. In the case of the adults evaluation took place after 2 weeks, and ;n that of the larvae after 2 days. Each test was repeated twice.
:
'~ B) Boophilus microplus (larvae) ~, .
; Tests were carried out in each case with 20 OP-sensitive ,, larvae using an analogous dilution series as in the case of ~;
;:~ test A. (The resistence refers to the tolerability of Diazinon).
,~ :
' The compounds according to Example 1 acted in these - tests against adults and larvae of Rhipicephalus bursa sensi-tive and OP-resistent larvae of Boophilus microplus.
Example 3 Action against Chilo suppresalis .
Six rice plants at a time of the variety Caloro' were transplanted into plastic pots (diameter at the top = 17 cm) and reared to a height of about 60 cm. Infestation with Chilo ~ 31 _ : :
-- - " 1047~39 , . , ` suppressalis lar~ae (Ll: 3-4 mm long) took place 2 days after the active substance had been applied in granule form to the paddy water (rate of application: 8 kg of active substance per hectare). Evaluation of the insecticidal action took place 10 days after application of the granules.
. .
. The compounds according to Example 1 were active in the ~- above test against Chilo suppressalis.
. .
Example 4 ,.
~ Action against soil insects !,:
,`",'~ .
Sterilised compost earth was homogenously mixed with a `~ wettable powder containing 25% of active substance so that there resulted a rate of application of 8 kg of active sub-stance per hectare.
Young zucchetti plants (Cucumis pepo) were put into plastic .::
pots with the treated soil (3 plants per pot; diameter of pot ~; = 7 cm). Each pot was infected immediately afterwards with 5 ".
; Aulacophora femoralis and Pachmoda or Chortophila larvae. The ~; control was carried out 4, 8, 16 and 32 days after depositing~,~ the larvae.
' At 80-100% kill after the first control, a fresh infesta-tion with 5 larvae each was carried out in the same soil sample with 3 new zucchetti plants. If the activity was less than ` 80%, the remaining larvae remained in the soil sample until the control immediately following . If an active substance at a rate of application of 8 kg/ha still effected a 100% kill, ~ ` `
~ . --~047~89 ~:; a further control with 4 and 2 kg of active substance per hectare was carried out.
.
In the above test, the compounds according to Example 1 displayed action against Aulacophora fermoralis, Pachmoda and ; Chortophila larvae.
~ Example S
- Acaricidal action ` Phaseolus vulgaris (dwarf beans) have 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 have migrated are sprayed with the emul-sified test preparations from a chromatography atomiser so that the spray broth does not run off. The number of living s and dead larvae, adults and eggs are evaluated after 2 to 7 -days under a stereoscopic microscope. During the "interim", the .; treated plants are kept in greenhouse compartments at 25C.
The compounds according to Example 1 were active in the .: .
above test against eggs, larvae and adults of Tetranychus -. . .
urticae.
Example 6 Action a~ainst soil nematodes To test the action against soil nematodes, the active substance is .
r :' , ' ~ ln47~ss applied to and intimately mixed with soil infected with root j; .
'~ gall nematodes (Meloidgyne Arenaria), Immediately afterwards, ' tomato cuttings are planted in the thus prepared soil in a series of tests and after a waiting time of 8 days tomato , seeds are sown in another test series.
In order to assess the nematocidal action, the galls present on the roots are counted 28 days after planting and sowing respectively. In this test the compounds according to Example 1 display good action against Meloidgyne Arenaria.
.:
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r, ' 6-methyl-2-oxo-1,3-dithiolo-[4,5-b]-quinoxaline (Quino- -~: 15 methi.onate~ -'!: (I)-3~(2-furfuryl)-2-methyl-4-oxocyclopent-2-enyl(I)-(cis-~
trans)-chrysanthemum-monocarboxylate ~Furethrin3 2-pivaloyl-inclane-1,3 dione [Pindon]
4-chlorobenzyl-4-fluorophenyl-sulphide [Fluorobenside]
5,6-dichloro-1-phenoxycarbamyl-2-trifluoromethyl-benzimidazole [Fenozaflor]
p-chlorophenyl-p-chlorobenzenesulphonate [Ovex]
p-chlorophenyl-benzenesulphonate [Fenson]
~047489 p-chlorop'lenyl-2,4,5 trich].orophenyl.st~ 0ne [Tcl:radi:Eon~
p- clllorophenyl-2,4,5-trichlo~o~ ylsull)hj-.1e ~JTel~rasul~
p - ch] oroben~l p - chlorophenyl sulphicle [ Ch:l orobens i de ]
2 - thio ~l , 3--dithiolo- (5, 6) -qulnoxaline [Thiochinox ]
prop-2-ynyl-(4-t-butylphenoxy)-cyclohe~ylsulphite [Propargil].
l~ormam;.dines ~, , . _ .
l-dimechyl-2- (2 ' -met:hyl-4' -chlorophenyl) -formamidine (CELC~ODIM~
l-metl-yl-2-(2' methyl-4~-chlorophenyl)-~ormc.midi.ne 1-methyl-2- (2 ' -methyl-4' -bromophenyl) -~ormamidine l-methyl-2 - (2 ', 4 ' -dime thylphenyl ) - formamidine l-n-butyl-l-methyl-2- (2 ' -me~hyl -4' -chloro~henyl) -Eormamidine l~methyl-l- (2 ' -methyl-4' -chloroaniline-met:llylene)-~ormarnidi.ne 2- (2"-methyl-4"-chlorophenyl-formamidine :~
l-n butyl-2- (2 ' -methyl-4' -chlorophenyl-imino) -pyrolidine Urea N-2-methyl-4-chlorophenyl-N' ,N' -dimethyl-thiourea Carbamates l~naphthyl-N-methylcarbamate (CARBARYL) .: .
2--butinyl-4-chlorophenylcarbamate 4-dimethylamino-3,5-xylyl-N-methylcarbarllate - 4-dimethylamino-3-tolyl-N-methylcarbamate (AMINOCARB) 4-methylthio-3,5-xylyl-N-methylcarbamat:e (ME:T~IIOCAP~B) 3,4,5-trimethylphenyl-N-methylcarbamate 2-chlorophenyl-N-methylcarbamate (CPMC) . , , , . ' ' ' , .' ' " .
:; ~
~047 ~; 5 cllloro-G-o;o~2-no~borarle carbonitrile~O~ etllylcarbamoyl)~
~ -,, .
. oxime ,", 1-(dime~ $~1c~ba}noyl-5~me~1lyl 3-pyra~:olyl~N,N-dimetllylcarba mate (DI~ETILA~l) 2,3-dihydro-2,2-dimethyl-7-benzofuLanyl-N-metllylcarbamate , (CARBOFUR~N) ,,.', 2-methyl-2-me~hylthio-propionaldehyde-0-(metllylcarbamoyl)-ox:Lme (ALDICARB) ;~: 8-quinaldyl-N-methylcarbamate and its salts.
methyl-2-isopropyl-4-(methylcarbamoyloxy)carbanilate m-(l-ethylpropyl)phenyl-N-methylcarbamate 3,5-di-tert.butyl--N-methylcarbamate m-(l methylbutyl)pllenyl-N-methylcarbamate 2~isopropylphenyl-N-methylcarbamate ;. 15 2-sec.butylphenyl-N-methylc2rbamate :, ~ m-tolyl-N- methylcarbamate , -2,3-xylyl-N-methylcarbamate 3-isopropylphenyl-N-methylcarbamate 3-tert.butylphenyl-N-methylcarbamate . 20 3-sec.butylphenyl-N-methylcarbamate ; . 3-isopropyl-5-methylphenyl-N-methylcarbamate (PRO~EC~RB) 3,5-diisopropylphenyl-N-methylcarbamate - 2-chloro-5-isopropylphenyl-N-methylcarbama~e 2-chloro-4,5-dimethylphenyl-N-methylcarbamate 2-(1,3-dioxolan-2-yl)phenyl-N-methylcarbamate (DIOXACARB) ~` ~047~89 :
,S-dir.letl~ .-1,3-dioxolan-2-yl)-pllenyl~ net:hylcarbamate 2-(1,3-dioi~olan~~-yl)pllenyl-N,~I-dimetllylc~rbam~te 2-(1,3-di ~.hiolan-2-yl) N,N-di.methylcarbamat:e 2-(1,3-dith;olan-2-yl)phenyl-N,N-clim~tllylcarlamate , - 5 2-isopropoxyphenyl-N-me~hylcarbamate (APROC~B) 2-(2-prop;nyloxy)phenyl-N-methylcarbarnate 3-(2--propinyloxy)phenyl-N-me,llylcarbamate 2-dimetllylaminophenyl-N-methy:lcarbamate -~
2-diallylaminophenyl-N-met:hylcarbamate ~-~-di.allylamino-3,5-xylyl-N-methylcar~am2te (ALL~'XICARB) 4-benæothienyl-N-methylcarbamate 2,3-dihydro--2-me~llyl-7-ben~o~uranyl-N--methy].carbamate : 3-methyl-1-phenylpyrazol-5-yl-N,N-di.methylcarbamate l-isopropyl-3-methylpyrazol-~-yl-N,N dimethylcarl~amate (ISO~N) 2-dimethylclmino-5,6-dimethylpyrimidin-4-yl-N,N-dimethyl-carbamate3-methyl~-dimethylaminomethyleneiminophenyl N-methyl-carbamate 3,4-dimethylphenyl-N-methylcarbamate 2-cyclopentylphe~-N-methylcarbamate 3-dimethylamino-metllyleneiminophenyl-N-methylcarbamate (FO~METANATE) and its salts ~ :
l-methylthio-ethylimino-N-methylcarbamate (METHOMYL) 2-methylcarbamoyloximino-1,3-dithiolane .~ -5-methyl-2-methylcarbamoyloximino-1,3-oxythiolane ' ~
' ~0474ss 2 (1-me~hoxy-2 propo,~y)ph~nyl~ -tne~hylcarbaMate 2~ utin-3-yl-o~)phenyl-N-~l~e~llylca~l~aMa~e :1. c1i.metl~yl.carbamyl-l-me~ y].t:llio-O-me~h,71carhalrlyl-formoxime 1-(2~-cyanoethylthio)-0-methylcarbamyl-acetaldo~f.lme ]-methylthio-0-carbamyl~acetalcloxime 0-(3-sec.butylphenyl)-N-pllenyltllio~N-methylcarballJate 2,5-dime~hyl-1,3~dithiolane-2-(0 methylcarbarnyl)-aldoxime) 0-2-diphenyl-2~-metllylcarbamate ~` 2-(~-methylcarbamyl-oximino)~3-chloro-bicyc~o[2.2,1]lleptane 2-(N-me~hylcarbamyl-oximino)-bicyclo[2.2,1]heptane 3-isopropylphenyl-N-methyl-N-cllloroacetal-carbamate 3-isopropylphenyl-N-mcthyl-~-methy].thiome~hyl-ca-rbamate '~
.~ 0-(2,2-dimethyl-4-chloro-2,3-dihydro-7-benzofuranyl)-N-methyl-. .
carbamate 0-(2,2,4-trimethyl-2,3-dihydro-7-benzofuranyl)-N-methylcarba-rnate 0-naphthyl-N-methyl-N-acetal-carbamate 0-5,6,7,~-tetrahydronaphthyl-N-methyl-carbamate 3-isopropyl-4-methylthio-phenyl-N-methylcarbamate 3,5-dimethyl~4-methoxy-phenyl-~-methylcarbamate 3-methoxymethoxy-phenyl-N-metllylcal-bamate 3-allyloxyphenyl-N-methylcarbamate 2-propargyloxymethoxy-phenyl-N-methyl-carbamate 2-allyloxyphenyl-N-methyl-carbamate 4-methoxycarbonylamino-3-isopropylphenyl-N-methyl-carbamate 3,5-d;rn~l Hy~ metl~c)x~Jcarbollylamino-pheny-l-N-methyl-carbama~e ~-y-me~l-y~ iol~o~y~ eny]~ nethyl- ca~ a~ -3-(a-netlloxym~thyl-2-propeilyl)-phenyl~N-methyl-carbamate 2 chloro-5-tert.-butyl-phcny]-N-metllyl-carbamate 4~(methyl-propargylamino 3,5-xyly].~N--methyl-carbamate 4-(methyl-y-cl-lloroallylalllino)-3,5-~ylyl-N--met:hyl-carbamate 4-(methy]-~-chloroallylamino)-3,5-xylyl-N-methyl-ca]^bamate l-(~-ethoYyca~:bonylethyl) 3-methyl-5-pyrazolyl-N,N-dimethyl-carbamate ; 10 3- methyl-4 (dimethylamino-methylmercapto-methyleneimino)-phenyl-N methyl-carbamate 1,3-bis(carbamoylthio)-2-(N,N-dimethylamino)-propanehydro-:, chloride 5,5-dimethylhydroresorcinoldimethylcarbamate 2-[ethyl-propargylamino]-phenyl.-N-methylcarbamate .` 2-[methyl-propargylamino]-phenyl-N-methylcarbamate ~ 4-[dipropargylamino]-3-tolyl-N-methylcarbama~e '< 4-[dipropargylamino]-3,5-xylyl-N-methylcarbamal:e ~ '.
! 2-~allyl-isopropylamino]-phenyl-N-methylcarbamate 3-[allyl-isopropylamino]-phenyl-N-methylcarbamate ; Chlorinated Hydrocarbons y-hexachlorocyclohexane [GAMMEXANE; LINDAN; y HCH]
~., 1,2,4,5,6,7,8,8-octachloro-3a,4,7,7a -tetrahydro-4,7-- methylene indane ~CHLORDAN]
1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-.
. . .
, methylene indane 1,2,3,4,10,10-hexachloro-1,4,4~,5,8,8~-hexahydro-endo-1,4-exo-5,8-dimethano-naphthalene 1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4~,5,6,7,8,8~-octahydro-exo-1,4-endo-5,8-dimethanonaphthalene 1,2,3,4,10,10-hexachloro-5,7-epoxy-1,4,4~,5,6,7,8,8~-octahydro-endo-endo-5,8-dimethanonaphthalene.
: The compounds of the formula I are also suitable for combatting plant pathogenic nematodes.
: 10 The compounds of the formula I may be used as pure active sub-stance or together with suitable carriers and/or additives. Suitable - carriers and additives can be solid or liquid and correspond to the sub-stances conventionally used ,~
;' .~
,, h -19-~0~7489 in formula~ioI2 tccllnique such, fo~ e~ample, as solvcnts, <lispersclllts, ~e~ g agel-lts, a~lllesives, tllickeners~ binders and/o-r fcl^tilisers.
For application, the compounds of the forrnula I may ; 5 be processed to dusts, emulsion concentrates, granllles, dis~
persions, sprays, to solu~ions, or suspensions, in the con-- ventiona] form-llation which is co~nonly en-ployed in app]i cation technology ~lention may al~so be made o~ cattle dips and spray races, in which aqueous preparations are used.
-~ 10 The agents according to the invention àre manuac-tùred in lcnown manner by intimately mixing and/or grinding active sul~stances of the for~ula I with the suitable carriers, optionally with the addition of dispersants or solvents WlliCIl are inert towards the active substances. The active subs~ances may take, and be used in, the following forms:
Solid forms:
Dusts, tracking agents, granules, coa~ed granules, impre~nated granules and homogeneous granules.
Liquid forms: i a) active substances which are dispersible in water:
wettable powders, pasts, emulsions; ~ ;
b) solutions.
To manufacture solid forms (dusts, tracking agents), the active substances are mixed with solid carriers. Suit-able carriers are, for example: kaolin, talcum, bolus, loess, , . . .
~)47489 chalk, limes~one, ground limes~olle, a~ac]ay, dolomite, ;-diatomacec)us ea-rth, precipita~cd silica, alkaline earth sili.cates, sodium and potassium alumin:ium silica~e~s (feld-spar and mica), calcium~d inagnesium su]phates, magnesium : 5 o~ide, ground synthetic materials, fertilisers, ~or example `-- ammonium sulphate, ammonium phosphate, ammonium ni~rate, : urea, ground vegetable products, such as corn meal, bark .:
dust, sawdust~ nutshell meal, cellulose powcler, residues o plant extract:ions, activated charcoal etc These substances can either be used singly or in admixture ~ith one another.
:- Granules can be very eas:lly manufactured by dissol-ving an active substance of the formula I in an o~ganic solvent and applying the resul~ing solution to a granulated material, for example attapulgi~e, SI02, granicalcium, belltonite etc and then evaporating the solvent.
Polymer granules can also be manuf~c~ured by mixin;, ; the active substances of the formula I with pol~erisable compounds (urea/formaldehyde; dicyandi2mide/formaldehyde;
melami.ne/formaldehyde or others), whereupon a mild polyn~eri-sation is carried out that does not affect the active substances and in the process of which the granulation is carried out during the gel formation It is more advantageous to impregnate finished, porous polymer granules (urea/
formaldehyde, polyacrylonitrile, polyester or others) ~Jhich have a specifi.c surface area and a favourable predeterminablF:
n47~8 : " ' - adsorption/desorption ratio, with the ac~ive substances, ~or example in th~ orm of th~ir solutions (in a lo~ boiling solvent) and to remove ~he solvent. Polymer granules of this kind in the ~o~m of microgranules having a bulk density of ~, ....
- 5 300 g/liter to 600 g/liter can also be manu~actured ~ith the aid of atomisers. The dusting can be carried out from aircrat .~ :
over extensive areas of cultures of useful plants.
. . It is also possible to obtain granules by compacting ~ .
.. the carrier ~ith the active substan.ce and carriers and subsc-- 10 quently com~linu~ing the product.
To tllese mixtures can also be a.dded additives which ;. stabi.lise the active substance and/or non-ionic, anioni.c arld ~., .
. cationic sur~ace active substances, whicll, for example, improve the adhesion of the active ingredients on plants or parts o plants (adhesives and agglutinants) and/or ensure a better wettability (wetting agents) and dispersibility (dispersirg agents). Examples of suitable adhesives are the following: olein/chalk mixture, cellulose derivatives (methyl ::
cellulose, carboxymethyl cellulose), hydroxyethyl g]ycol - .
: 20 . ethers o monoalkyl and diallcyl phenols having 5 to 15 ethylene ox;de radicals per molecule and 8 to 9 carbon atoms ; in the alkyl radical, lignin sulphonic acids, their alkali metal and alkaline earth metal salts, polyethylene glycol ethers (carbowaxes), ~atty alcohol polyethylene glycol ethe~s having 5 to 20 ethylene oxide radicals per molecule and 8 to . .
.. . .. .. .. .. .. ..
ln47489 . .
18 carbon atoms in thc atty a]cohol moiety, condensation produc~s o~ e~hylene oxide/propylcne oY~ide, polyvinyl pyrro-lidones, polyvinyl alcohols, con~ensation products of urea and ormaldehyde, and also late~ products.
The ~ater-dispersible concentratcs of the active substance, i.e. ~ettable po~ders, pastes and emulsiiable concentra~es, are agents whicll can be diluted wi~l-l water to . . , ~ any concentra~ion desirecl. They consist of active substance, .... .
~ carrier, opti~nally additives which stabilise the active - 10 substance, sur~ace-active sùbstance and anti-foam agents ; and, optionally,solvents.
. .
l~ettable powders and pastes are ob~ained by ml~ g and grinding the active substances with dispersing agents and ~ulverulent c~rriers in suitable apparat-us un~il homogeneity is attained. Suitable carriers are, for exam.ple, those men-tioned for the solid forms of application. In some cases it is advantageous to use mixtures of dif~erent carriers. As dispersing agents there can be used, for example, condensation products o~ sulphonated naphthalene and sulphonated naphtha lene derivatives with formaldehyde, condensation products o~
naphthalene or naphthalene sulphonic acids with phenol and formaldellyde, as well as-alkali, ammonium and alkaline earth me~al salts of lignin sulphonic acid, in addition, allcylaryl ~ sulphonates, alkali and alkaline earth metal salts o~ dibutyl : 25 naphthalene sulphonic acid, fatty alcohol sulphates such as .~,, , ,,, ,, ,., ,. , . , ., _ .
' ~
-` ~0474t39 ~:
salts of sulpllated hexadecanols, heptadecanols, octadecanols, and salts o suli~ha~ed ~atty alcol~ol glyco] e~hers, the sodiurll salt o~ oleoyl e~hionate, t}-le soclium salts o oleoyl methyl taurid~, ditertiary acetylene glyco]s, dialkyl di-~`~ 5 lauryl a~nonium chloride and fa~ty acid alkali and alkaline earth metal salts.
Suitable anti-fo~m agents are silicones.
The active substances are mixed~ gro~md, sieved and strained ~ith the additives cited hereinabove, in such a manner that, the size of the solid particles does not exceed 0 02 to 0,04~in wettable po~ders, and 0.03~ in past-es.
i To produce emulsifiable concentrat~es and pastes, dispersing .~ agents such as those cited above, organic solvents, and water are used. Examples of suitable solvents are: a]cohols, benzene, xylene, toluene, dimethyl sulphoxide, and mineral oil fractions which boil between 120 and 350C. The solvents must be ~
pract-ically odour]ess, not phytotoxic, and inert to the active -substances.
Furthermore, the agents accor~ing to the invention 20 can be applied in the form of solutions. For this purpose -~
: . :
v the active substances, or several ac~ive substances of the `
general ormulà X, are dissolved in sui~ab]e organic solvents, mixtures of solvents or in water Aliphatic and aromatic h~r~ ~-drocarbons, chlorinated derivatives thereof, alkyl naphthalene~
25 and mineral oils, singly or in admixture wi~h each other, can ,... .
J
.
' " .. .... ... . .... .... .... . ... .. . .. . . . . .
, . . .
. .
`;~ 1(~4~ 9 .. ~ .
43.~ parts of xylene.
~- b) 25 parts of active s~lbstance, ;- 2 5 parts of epoxidised vegetable oil, parts of an alkyl.arylsulphonate/fatty alcohol--polyglycol ether m:i~ture, . 5 parts o dimethylforrllamide, . 57.5 parts of xylene.
~` . From ~hese concentra~es i~ is possible to pro~lce, by dilution ~.7:ith ~.7ater, emulsions o any desired concentra tion.
- Spray:
The ~ollowing constituents are used to prepare a 5% spray:
: 5 parts of active subs~:ance, .. 15 1 part of epichlorohydrin, 94 parts of benzine (boiling limits 160~ - 190C).
~ ' ~
,, .
., ' , ~
,, ''"
'~ ' .
. .
- ~ , .
, 1.7 parts of Chami~agn~ chalk/hydroxyethyl cellulose : mi~ture (1:1), ~-J '~ ~. 3 parts of sodium aluminium silicate, lG.5 parts of kieselguhr, 46 parts of kaolin d)10 parts o active substance, 3 par~s of a mix~ure of the sodium salts of :~ saturated fatty alcohol sulphates, : ..... .
~:: 5 parts of naphthalenesulpllonlc acid/~ormaldehyde ~ "
condensate, 82 parts o kaolin.
- ~ The active substances are intimately mixed, in suit-able Ir~ixers, with the additives, the mixture being then ground ~;.: ~ - .
, in tlle appropriat-e mills and rollers. Wettable po~ders are :: 15 ob~ai.ned which can be diluted ~7ith ~Jater to give suspensions ... .
- of any desired concentration.
.~. .
~;' mul ial~ e concentrates:
i.l .
.. The ollo~ing substances are used to produce a) a 10% and b) a 25% emulsifiable concentrate:
a) 10 parts o active subs~ance, A l3.4 parts of epoxidised vegetable oil~
13.4 parts of a combination emulsifier consisting - of fatty alcohol polyglycol e~her and alkyl-arylsulphonate calcium salt, " .
s 25 bO parts of dimethylformamide, ,,"
- 26 _ .. .. . ... . ..... ... ... ... ... . ....... . . ... . .... .. .. .... . .. ... . .. . ....... . .. . .. .. . . . . ..
,; . . - : ~ . - ., , ' ' ''. ~
9~89 3 . SO parts of polyethylelle glycol, 91 par~s of l~aoliII (particle size 0.3 - 0.8 mm).
The active substance is mixed witll epichlorohydrin : and dissolved wltll 6 parts of ace~olle; the polyethy]ene .
glycol alld cetyl polyglycol ethex are then adcled. The th~s ~:. o~tai.ned solution is sprayed on kaolin, and the ace~one - subsequellt].y e~raporated in vacuo.
I~ettable pow~er:
Th~ following constituen~s are used for the pre-10 paration of a) a 40%, b) and c) a 25%, and d) a 10% wettable T~Wder:
.~ a)40 par~s of active substance, , parts o sodium lignin sulphonate, 1 part of sodium dibu-~yl-naph~halene sulphonate, 54 par~s of silicic acid, .. ~ b) 25 parts of active substance, 4.5 parts of calcium lignin sulphona~e, 1.9 parts o Champagne chalk/hydroxyethyl cellulose . mixtuxe (1:1), 1.5 parts of sodium dibutyl naphthalene sulphonate, . . ~ .
. 19,5 parts of silicic acid, 19,5 parts of Champagne chalk, 28,1 parts of kaolin.
c)25 paxts of active substance, 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, ,, , :
. . .
_ 27 -.
~ ' ~
be used as organic solvents.
The content of active substallce in the above des-cribed agents is be~een 0. l~/o to 95%, in wllicll connection it should be ment.ioned that, in the case of application from ~-aircra~ or soMe other suitable means of application, it is possible to use concen~rations of up ~o 99.5% or even pure ac~ive substance. -The active substances o the fonllula I can, for example, be formulated as follows:
~ .
~ 10 Dusts :
The follo~Jing substances are used to manufacture a) ~ a 5% and b) a 2% dusc:
a)5 parts o active substance 95 parts of talcum - 15 b)2 parcs of active substance , 1 part of highly disperse silicic acid c 97 parts of talcum.
The active substances are mixed with the carriers and ground.
~,; 20 Granules ;~ The following substances are used to produce 5%
,ji granules:
- 5 parts of active substance, 0,25 parts of epichlorohydrin, - 25 0 25 parts of cetyl polyglyco] eLher~
.
, :
. ,.,.. ,,.. ,., . ,,.. ,.,.. . ,,.. ,, ,., .,. , . .. ,, .. , ~ .
~047489 - Example 1 : ~ S
At room temperature 10.1 g of 0-ethyl-~-(n)-propyl-thio~-~phosphoric chloride in 2~ ml of absolute ether are added dropwise to a solution of 11.6 g of 4-hydroxy-4'-chloro-azo benzene and 5.1 g of triethylamine in 150 ml of absolute ether.
The salt precipitate is filtered off and the mixture is treated with 200 ml of ice water with stirring. The organic phase is isolated, washed once with water and shaken twice with ice-cold "
~ 5% sodium hydroxide solution and then washed neutral with ,. .
. water. The ethereal phase is then treated with activated char-coalJ filtered, dried, and the solvent is evaporated. The resi-r: i , due is dried for 3 hours at 70C and 0.1 Torr to give the com-~; pound of the formula ,;
.. , O
` C1~3N=N~3 ~S) C ~I ( n ) , ................................................ . .
r~,' with a refractive index of n20 1.6185.
The following compounds are also manufacture in analogous manner:
, . . . .
.
: ~N=~o-~a3~l7(n~ nD20= 1,6142 ` ~
ri~ ~ O .. ' : .
-- ~==~ ~==\ 11 /OC2H
,- Cl ~ N=N ~ ~SC3H7(n) D - 1,6251 ''` ' ' .
, ~ .
-~
:.
. :
- 1047~39 `. S
Cl~N=I~-~ 11 <3CzH5 nD20 SC3H7(n) = 1,6345 . C 1 ,. I , O .::
C1~3N--N~ C3H7(n) nD20 _ 1, 6300 ,. o " CH3~~ `~ 3 7 ( ) nD2 = 1, 6132 :
C1~3-N=N~~,<OC E5 nD - 1, 6495 'i Cl S
~=~ ~c=~11 /OC H
~ ~ ~N=N~ 3 7 ( nD ~ 1, 6348 ;:' S
i~, CH~ ~N~3 3 7 ( ) n20 = 1, 6336 ..
~' O
11 ~OC H
~,~ ~N--N~o--P< 2 5 CH n2o ., - SCH2--CH< 3 D - 1, 6082 0~I3 Cl~3N-N~ ~<OC2H5 20 SCH2--CH<~3 nD = 1, 6078 ~" .
: . ' ~, ~
. , .
Example 2 1047~89 ~,, ' .
~ction against ticks .
~ A) Rhipicephalus bursa , . .
Five adult ticks and 50 tick larvae were counted into a glass tube and immersed for 1 to 2 minutes in 2 ml of an aqueous emulsion from an emulsion series each containing 100, ; 10, 1 and 0.1 ppm f test substance The tube was then sealed ~ . .
with a standardised cotton wool plug and placed on its head, so that the active substance emulsion could be adsorbed by the cotton wo~l.
. In the case of the adults evaluation took place after 2 weeks, and ;n that of the larvae after 2 days. Each test was repeated twice.
:
'~ B) Boophilus microplus (larvae) ~, .
; Tests were carried out in each case with 20 OP-sensitive ,, larvae using an analogous dilution series as in the case of ~;
;:~ test A. (The resistence refers to the tolerability of Diazinon).
,~ :
' The compounds according to Example 1 acted in these - tests against adults and larvae of Rhipicephalus bursa sensi-tive and OP-resistent larvae of Boophilus microplus.
Example 3 Action against Chilo suppresalis .
Six rice plants at a time of the variety Caloro' were transplanted into plastic pots (diameter at the top = 17 cm) and reared to a height of about 60 cm. Infestation with Chilo ~ 31 _ : :
-- - " 1047~39 , . , ` suppressalis lar~ae (Ll: 3-4 mm long) took place 2 days after the active substance had been applied in granule form to the paddy water (rate of application: 8 kg of active substance per hectare). Evaluation of the insecticidal action took place 10 days after application of the granules.
. .
. The compounds according to Example 1 were active in the ~- above test against Chilo suppressalis.
. .
Example 4 ,.
~ Action against soil insects !,:
,`",'~ .
Sterilised compost earth was homogenously mixed with a `~ wettable powder containing 25% of active substance so that there resulted a rate of application of 8 kg of active sub-stance per hectare.
Young zucchetti plants (Cucumis pepo) were put into plastic .::
pots with the treated soil (3 plants per pot; diameter of pot ~; = 7 cm). Each pot was infected immediately afterwards with 5 ".
; Aulacophora femoralis and Pachmoda or Chortophila larvae. The ~; control was carried out 4, 8, 16 and 32 days after depositing~,~ the larvae.
' At 80-100% kill after the first control, a fresh infesta-tion with 5 larvae each was carried out in the same soil sample with 3 new zucchetti plants. If the activity was less than ` 80%, the remaining larvae remained in the soil sample until the control immediately following . If an active substance at a rate of application of 8 kg/ha still effected a 100% kill, ~ ` `
~ . --~047~89 ~:; a further control with 4 and 2 kg of active substance per hectare was carried out.
.
In the above test, the compounds according to Example 1 displayed action against Aulacophora fermoralis, Pachmoda and ; Chortophila larvae.
~ Example S
- Acaricidal action ` Phaseolus vulgaris (dwarf beans) have 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 have migrated are sprayed with the emul-sified test preparations from a chromatography atomiser so that the spray broth does not run off. The number of living s and dead larvae, adults and eggs are evaluated after 2 to 7 -days under a stereoscopic microscope. During the "interim", the .; treated plants are kept in greenhouse compartments at 25C.
The compounds according to Example 1 were active in the .: .
above test against eggs, larvae and adults of Tetranychus -. . .
urticae.
Example 6 Action a~ainst soil nematodes To test the action against soil nematodes, the active substance is .
r :' , ' ~ ln47~ss applied to and intimately mixed with soil infected with root j; .
'~ gall nematodes (Meloidgyne Arenaria), Immediately afterwards, ' tomato cuttings are planted in the thus prepared soil in a series of tests and after a waiting time of 8 days tomato , seeds are sown in another test series.
In order to assess the nematocidal action, the galls present on the roots are counted 28 days after planting and sowing respectively. In this test the compounds according to Example 1 display good action against Meloidgyne Arenaria.
.:
~'. .
, .
t..
r.;
~ :
,~' ,'.
:,.';~;
~5'~ .
,~,, ~''' ' .. , -- . . . .
. ~ .
, ,'. ~ ~ .
~, ~'' .
~. .
.,:
': :
' .
,...
i' , -, ..
~ ~ .
Claims (26)
OR PROPERTY IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Compounds of the formula I
(I) wherein each of R1 and R2, which may be the same or different, represents an alkyl group containing 1 to 5 carbon atoms, each of R3 and R4, which may be the same or different, represents a halogen atom or an alkyl group containing 1 to 5 carbon atoms, X represents an oxygen or sulphur atom, n is zero or an integer from 1 to 4 inclusive and m is zero or an integer from 1 to 5 inclusive.
(I) wherein each of R1 and R2, which may be the same or different, represents an alkyl group containing 1 to 5 carbon atoms, each of R3 and R4, which may be the same or different, represents a halogen atom or an alkyl group containing 1 to 5 carbon atoms, X represents an oxygen or sulphur atom, n is zero or an integer from 1 to 4 inclusive and m is zero or an integer from 1 to 5 inclusive.
2. Compounds as claimed in claim 1 wherein R1 represents a propyl or butyl group and R2 represents an ethyl group.
3. Compounds as claimed in claim 2, wherein R1 represents an n-propyl group.
4. Compounds as claimed in claim 1 or 2 wherein X represents an oxygen atom.
5. Compounds as claimed in claim 3 wherein X represents an oxygen atom.
6. Compounds as claimed in claim 1 or 2 wherein X represents an oxygen atom, n is zero or 1 and m is zero, 1 or 2.
7. Compounds as claimed in claim 5 wherein n is zero or 1 and m is zero, 1 or 2.
8. Compounds as claimed in claim 5 wherein each of each of R3 and R4, which may be the same or different, represents a chlorine atom or a methyl group.
9. Compounds as claimed in claim 7 wherein each of R3 and R4, which may be the same or different, represents a chlorine atom or a methyl group.
10. A compound according to claim 1 of the formula
11. A compound according to claim 1 of the formula
12. A compound according to claim 1 of the formula
13. A compound according to claim 1 of the formula
14. A compound according to claim 1 of the formula
15. A compound according to claim 1 of the formula
16. A compound according to claim 1 of the formula
17. A compound according to claim 1 of the formula
18. A compound according to claim 1 of the formula
19. A compound according to claim 1 of the formula
20. A compound according to claim 1 of the formula
21. A method of combatting pests of the class Insecta or of the order Acarina at a locus, which method comprises applying to the locus a compound as claimed in any one of claims 1 to 3.
22. A method of combatting pests of the class Insecta or of the order Acarina at a locus, which method comprises applying to the locus a compound as claimed in any one of claims 5, 7 or 8.
23. A method of combatting pests of the class Insecta or of the order Acarina at a locus, which method comprises applying to the locus a compound as claimed in claim 9 to 11.
24. A method of combatting pests of the class Insecta or of the order Acarina at a locus, which method comprises applying to the locus a compound as claimed in claim 10.
25. A method according to claim 24 wherein the locus comprises growing agricultural or horticultural crops or plants.
26. A method according to claims 24 or 25, wherein the pests are insect pests.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1021072A CH570763A5 (en) | 1972-07-07 | 1972-07-07 | Azobenzene organophosphorus esters - useful as insecticides and acaricides |
| CH672073 | 1973-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047489A true CA1047489A (en) | 1979-01-30 |
Family
ID=25700052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA175,820A Expired CA1047489A (en) | 1972-07-07 | 1973-07-06 | Esters |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5414652B2 (en) |
| CA (1) | CA1047489A (en) |
| DE (1) | DE2334099C3 (en) |
| EG (1) | EG11409A (en) |
| FR (1) | FR2192111B1 (en) |
| GB (1) | GB1404387A (en) |
| IL (1) | IL42480A (en) |
| IT (1) | IT1054135B (en) |
| NL (1) | NL7309270A (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL102448C (en) * | 1956-11-07 |
-
1973
- 1973-06-11 IL IL42480A patent/IL42480A/en unknown
- 1973-07-03 NL NL7309270A patent/NL7309270A/xx not_active Application Discontinuation
- 1973-07-04 DE DE2334099A patent/DE2334099C3/en not_active Expired
- 1973-07-05 EG EG261/73A patent/EG11409A/en active
- 1973-07-06 JP JP7701473A patent/JPS5414652B2/ja not_active Expired
- 1973-07-06 FR FR7324958A patent/FR2192111B1/fr not_active Expired
- 1973-07-06 GB GB3233373A patent/GB1404387A/en not_active Expired
- 1973-07-06 CA CA175,820A patent/CA1047489A/en not_active Expired
- 1973-07-06 IT IT26308/73A patent/IT1054135B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2334099C3 (en) | 1979-10-25 |
| DE2334099A1 (en) | 1974-01-17 |
| DE2334099B2 (en) | 1979-02-15 |
| FR2192111B1 (en) | 1977-09-02 |
| NL7309270A (en) | 1974-01-09 |
| IT1054135B (en) | 1981-11-10 |
| IL42480A0 (en) | 1973-08-29 |
| GB1404387A (en) | 1975-08-28 |
| JPS4955844A (en) | 1974-05-30 |
| FR2192111A1 (en) | 1974-02-08 |
| JPS5414652B2 (en) | 1979-06-08 |
| EG11409A (en) | 1977-05-31 |
| IL42480A (en) | 1976-03-31 |
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