US3855362A - Phosphoric acid phenylsulphonamide esters - Google Patents
Phosphoric acid phenylsulphonamide esters Download PDFInfo
- Publication number
- US3855362A US3855362A US00310507A US31050772A US3855362A US 3855362 A US3855362 A US 3855362A US 00310507 A US00310507 A US 00310507A US 31050772 A US31050772 A US 31050772A US 3855362 A US3855362 A US 3855362A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- formula
- parts
- alkyl
- methyl
- 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 - Lifetime
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- JLISPDJKVHBDFX-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)N.P(O)(O)(O)=O Chemical class C1(=CC=CC=C1)S(=O)(=O)N.P(O)(O)(O)=O JLISPDJKVHBDFX-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- 239000000460 chlorine Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
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- 125000004432 carbon atom Chemical group C* 0.000 abstract description 36
- 125000000217 alkyl group Chemical group 0.000 abstract description 18
- 238000000034 method Methods 0.000 abstract description 8
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- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- BIWJNBZANLAXMG-UHFFFAOYSA-N chlordane Chemical compound ClC1=C(Cl)C2(Cl)C3CC(Cl)C(Cl)C3C1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-UHFFFAOYSA-N 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 229950002363 crufomate Drugs 0.000 description 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 1
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- VEENJGZXVHKXNB-VOTSOKGWSA-N dicrotophos Chemical compound COP(=O)(OC)O\C(C)=C\C(=O)N(C)C VEENJGZXVHKXNB-VOTSOKGWSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FAXIJTUDSBIMHY-UHFFFAOYSA-N diethoxy-(2-ethylsulfanylethoxy)-sulfanylidene-$l^{5}-phosphane;1-diethoxyphosphorylsulfanyl-2-ethylsulfanylethane Chemical compound CCOP(=O)(OCC)SCCSCC.CCOP(=S)(OCC)OCCSCC FAXIJTUDSBIMHY-UHFFFAOYSA-N 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ULUJSLFWDQSXRS-UHFFFAOYSA-N ethenyl diethyl phosphate Chemical compound CCOP(=O)(OCC)OC=C ULUJSLFWDQSXRS-UHFFFAOYSA-N 0.000 description 1
- VJYFKVYYMZPMAB-UHFFFAOYSA-N ethoprophos Chemical compound CCCSP(=O)(OCC)SCCC VJYFKVYYMZPMAB-UHFFFAOYSA-N 0.000 description 1
- OJZGWRZUOHSWMB-UHFFFAOYSA-L ethoxy-dioxido-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP([O-])([O-])=S OJZGWRZUOHSWMB-UHFFFAOYSA-L 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- JISACBWYRJHSMG-UHFFFAOYSA-N famphur Chemical compound COP(=S)(OC)OC1=CC=C(S(=O)(=O)N(C)C)C=C1 JISACBWYRJHSMG-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- XDNBJTQLKCIJBV-UHFFFAOYSA-N fensulfothion Chemical compound CCOP(=S)(OCC)OC1=CC=C(S(C)=O)C=C1 XDNBJTQLKCIJBV-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- RMFNNCGOSPBBAD-UHFFFAOYSA-N formetanate Chemical compound CNC(=O)OC1=CC=CC(N=CN(C)C)=C1 RMFNNCGOSPBBAD-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- GEPDYQSQVLXLEU-AATRIKPKSA-N methyl (e)-3-dimethoxyphosphoryloxybut-2-enoate Chemical compound COC(=O)\C=C(/C)OP(=O)(OC)OC GEPDYQSQVLXLEU-AATRIKPKSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- AGZFDMRWOVHNRR-UHFFFAOYSA-N methyl n-(1h-benzimidazol-2-yl)-n-(butylcarbamoyl)carbamate Chemical compound C1=CC=C2NC(N(C(=O)OC)C(=O)NCCCC)=NC2=C1 AGZFDMRWOVHNRR-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- GSVBOICPWQBKHQ-UHFFFAOYSA-N methylsulfanyl 3-amino-N-hydroxy-3-oxopropanimidate Chemical compound CSOC(CC(N)=O)=NO GSVBOICPWQBKHQ-UHFFFAOYSA-N 0.000 description 1
- IYSNYCQLARBERC-UHFFFAOYSA-N methylsulfinylmethane;toluene Chemical compound CS(C)=O.CC1=CC=CC=C1 IYSNYCQLARBERC-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 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 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([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])[H] 0.000 description 1
- PMCVMORKVPSKHZ-UHFFFAOYSA-N oxydemeton-methyl Chemical compound CCS(=O)CCSP(=O)(OC)OC PMCVMORKVPSKHZ-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
- 229950001664 phoxim Drugs 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000012219 potassium aluminium silicate Nutrition 0.000 description 1
- MHKFWKVLUPCEAH-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 MHKFWKVLUPCEAH-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- USDVAISJBZZCEZ-UHFFFAOYSA-N trihydroxy-[nitro(phenyl)-lambda4-sulfanylidene]-lambda5-phosphane Chemical compound OP(O)(O)=S(c1ccccc1)[N+]([O-])=O USDVAISJBZZCEZ-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
- 150000003738 xylenes Chemical class 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
Definitions
- the present invention relates to phosphoric acid phenylsulphonamide esters, a process for their manufacture and their use in pest control.
- R represents oxygen or sulphur
- R represents 7 alkyl with l to 5 carbon atoms
- R represents alkyl with l to 5 carbon atoms
- alkenyl and alkinyl each with 3 to 5 carbon atoms
- alkoxyalkyl with 1 to 5 carbon atoms in each of the moieties alkylthioalkyl with l to 5 carbon atoms in each of the moieties, or haloalkyl with l to 5 carbon atoms
- R represents hydrogen, alkyl with l to 5 carbon atoms or alkenyl with 3 to 5 carbon atoms
- R represents hydrogen and X and X, each represents halogen or alkyl with l to 5 carbon atoms
- R represents alkyl with l to 5 carbon atoms and X and Y R u j 1) P-Cl v H .R s j I (II) (III) Y R u P-Cl (II) (IV)
- Halogen is to be understood as meaning fluorine
- haloalkyl groups with l to 5 carbon atoms
- the groups cited hereinabove which are possible for .R to R X and X, may be straight-chain or branched.
- Examples of such groups include: methyl, methoxy, methoxymethyl, ethyl, ethoxyethyl, ethylthioethyl, propyl, isopropyl, n-, i-, sec. and tert.butyl, n-pentyl and the isomers thereof, allyl, methallyl, n-penten-S-yl, propargyl, isobutinyl.
- Preferred compounds on account of their action are those of the formula l, wherein R represents methyl or ethyl, R, represents propyl, n-butyl, n-pentyl or C H OCH CH R represents hydrogen, methyl or ethyl, R represents methyl or ethyl, X and X, each represents hydrogen or chlorine, and Y represents oxygen or sulphur.
- R and R each represents methylor ethyl
- X and X represent hydrogen or chlorine and Y represents oxygen.
- the compounds of the formula I can be manufactured according to methods'which are known per se:
- reaction temperature 0-12O C MeSH reaction temperature 0-100C essary to use catalysts in the reactions, e.g. copper or copper chloride.
- Processes l, 2, 3a and 3b may be carried out at normal pressure (3a at up to atmospheres absolute pressure) and in solvents or diluents.
- Suitable solvents or diluents are e.g., ethers and ethereal compounds, such as diethyl ether, dipropyl ether, dioxan, dimethoxyethane, tetrahydrofu'ran; amides, such as N,N-
- dialkylated carboxylic amides dialkylated carboxylic amides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, chloroform, chlorobenzene; nitriles, such as acetonitrile; dimethyl sulphoxide, ketones such as acetone, methyl ethyl ketone.
- the compounds of the formula I display a broad biocidal activity and are therefore suitable for combating various plant and animal pests and as plant growth regulators.
- the compounds of the formula possess insecticidal and acaricidalt properties which are superior to those of know, analogous compounds, and they may be used against all development stages, e.g., eggs, larvae, pupae, nymphs and addults, of insects and representatives of the order Acarina, for example against insects of the families:
- the active substances of the formula I are also suitable for combating representatives of the division Thallophyta, e.g., viruses, bacteria and fungi. They thus possess fungicidal properties against phytophathogenic fungi on various cultivated plants, such as cereals, maize, rice, vegetables, ornamental plants, fruit trees, vines, farms products, etc.
- the active sub stances of theformula I are active in particular against phytopahtogenic fungi belonging to the following classes: Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Denteromycetes.
- the new active substance can also be used for treating seeds, fruits, tubers etc., and the protecting them from fungus infections, for example from smut fungi of all kinds, such as Ustilaginales, e.g. Ustilago, Tilletia, Urocystis, Turbicinia and Phoma types.
- fungus infections for example from smut fungi of all kinds, such as Ustilaginales, e.g. Ustilago, Tilletia, Urocystis, Turbicinia and Phoma types.
- the compounds of the formula I are suitable for combating plant pathogenic nematodes.
- the compounds of the formula I may be used as pure active substance or together with suitable carriers and- /or additives.
- suitable carriers and additives can be solid or liquid and correspond to the substances conventionally used in formulation technique such, for example, as solvents dispersants, wetting agents, adhesives, thickeners, binders and/or fertilisers.
- the compounds of the formula I may be processed to dusts, emulsion concentrates, granules, dispersions, sprays, to solutions, or suspensions in the conventional formulation which is commonly employed in application technology. Mention may also be made of cattle clips and spray races," in which aqueous preparations are used.
- the agents according'to the invention are manufactured in known manner by intimately mixing and/or grinding active substances of the formula I with the suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active substances.
- the active substances may take and be used in the following forms:
- Dusts, tracking agents, granules, coated granules, impregnated granules and homogeneous granules are particularly preferred.
- the active substances are mixed with solid carriers.
- suitable carriers are, for example, kaolin, talcum, bo- Ius, loess, chalk, limestone, ground limestone, attaclay, dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminium silicates (feldspar and mica), calcium and magnesium sulphates, magnesium oxide, ground synthetic materials, fertilisers, for example ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, ground vegetable products, such as corn meal, bark dust, sawdust, nutshell meal, cellulose powder, residues of plant extractions, activated charcoal etc.
- These substances can either be used alone or in admixture with one another.
- Granules can be very easily manufactured by dissolving an active substance of the formula I in an organic solvent and applying the resulting solution to a granulated material, for example attapulgite, S10 granicalci um, bentonite etc. and then evaporatingthe solvent.
- a granulated material for example attapulgite, S10 granicalci um, bentonite etc. and then evaporatingthe solvent.
- Polymer granules can also be manufactured by mixing the active substances of the formula I with polymerisable compounds (urea/formaldehyde; dicyandiamide/formaldehyde; melamine/formaldehyde or others), whereupon a mild polymerisation 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.
- polymerisable compounds urea/formaldehyde; dicyandiamide/formaldehyde; melamine/formaldehyde or others
- porous polymer granules urea/formaldehyde, polyacrylonitrile, polyester or others
- the active substances for example in the form of their solutions (in a low boiling solvent) and to remove the solvent.
- Polymer granules of this kind in the form of microgranules having a bulk density of 300 g/litre to 600 g/litre can also be manufactured with the aid of atomisers. The dusting can be carried out from aircraft over extensive areas of cultures of useful plants.
- additives which stabilize the active substance and/or non-ionic, anionic and cationic surface active substances, which, for example, improve the adhesion of the active ingredients on plants or parts of plants (adhesives and agglutinants) and/or ensure a better wettability (wetting agents) and a dispersibility (dispersing agents).
- Suitable adhesives are the following: olein/chalk mixture, cellulose derivates (methyl cellulose, carboxy methyl cellulose), hydroxyethyl glycol ethers of monoalkyl and dialkyl phenols having 5 to 15 ethylene oxide 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), fatty alcohol polyethylene glycol ethers having 5 to 20 ethylene oxide radicals per molecule and 8 to 18 carbon atoms in the fatty alcohol moi ety, condensation products of ethylene oxide/propylene oxide, polyvinyl pyrrolidones, polyvinyl alcohols, condensation products of urea and formaldehyde, and also latex products.
- olein/chalk mixture cellulose derivates (methyl cellulose, carboxy methyl cellulose), hydroxyethyl glycol ethers of monoalky
- the water-dispersible concentrates of the active substance are agents which can be diluted with water to any concentration desired. They consist of active substance, carrier, optionally additives which stabilize the active substance, surface-active substanceand anti-foam agents and, optionally, solvents.
- W'ettable powders and pastes are obtained by mixing and grinding the active substances with dispersing agents and pulverulentcarriers in suitable apparatusuntil homogeneity is attained.
- Suitable carriers are, for example, those mentioned for the solid forms of application. In some cases it is advantageous to use mixtures of different carriers.
- dispersing agents there can be used, for example, condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, as well as alkali, ammonium and alkaline earth metal salts of lignin sulfonic acid, in addition, a]-
- kylaryl sulfonates alkali and alkaline-earth metal salts of dibutyl naphthalene sulfonic acid, fatty alcohol sulfates such as salts 'of sulfated hexadecanols, hep- 'tadecanols, octadecanols, and salts of sulfated fatty alcohol glycol ethers, the sodium salt of oleoyl ethionate, the sodium salt of oleoyl methyl tauride, ditertiary acetylene glycols, dialkyl fatty acid alkali and alkaline earth metal salts.
- Suitable anti-foam agents are silicones.
- the active substances are mixed, ground, sieved and strained with the additives cited hereinabove in such a. manner that, in wettable powders, the solid particle size of from 0.02 to 0.04 and in pastes, of 0.03 is notexdilauryl ammonium chloride and ceeded.
- dispersing agents such as those cited above,-organic solvents and water are used.
- suitable solvents are: alcohols, benzene, xylene, toluene dimethyl sulfoxide, and mineral oil fractions boiling between 120 and 350C.
- the solvents must be practically odourless, not phytotoxic, inert to the active substances.
- the agents according to the invention can be applied in the form of solutions.
- the active substance or several active substances of the general formula I are dissolved in suitableorganic solvents, mixtures of solvents or in water.
- suitableorganic solvents such as benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ethersulfate, benzyl ether, and benzyl ethersulfate, benzyl ether, and benzyl ethersulfate, benzylene glycol dimethoxysulfate, stearic acid, sulfate, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether ether sulfonyl sulfonyl sulfonyl
- the content of active substance in the above described agents is between 0.1 to 95 percent, in which connection it should be mentioned that, in the case of application from aircraft or some other suitable means of application, it is possible to use concentrations of up to 99.5 percent or even pure active substance.
- the active substances of the formula I can, for example, be formulated as follows: Dusts The following substances are used to manufacture (a) a 5 percent and (b) a 2 percent dust: v
- the activesubstance ismixed with epichlorohydrin and dissolved with 6 parts ofacetone; the polyethylene glycol and cetyl polyglycol ether are then added. The thus obtained solution is sprayed on to kaolin, and the acetone subsequently evaporated in vacuo.
- Wettable powder The following constituents are used for. the preparation of (a) a 40 percent, (b) and (d) a 10 percent wettable powder:
- EXAMPLE 1 play ingest poison action against Spodoplera litoratis and Leptinotarsa decemlineala.
- Systemic insecticidal action To determine the systemic action, rooted bean plants (Viciafabae) are put into a 0.01 percent aqueous active substance solution (obtained from a 10 percent emulsifiable concentrate). After 24 hours, aphids (Aphis fabae) are placed on the parts of the plant above the soil. The aphids are protected from contact and gas action by means ofa special device. The test is carried out at 24C and 70 percent relative humidity. In the above tests the compounds according to Example I displayed good insecticidal ingest poison action and systemic insecticidal action.
- Example 1 act in the above test against adults and larvae of Rhicephalus bursa.
- B. Boophilus microplus (larvae) Tests are carried out in each case with 20 OP- sensitive larvae using analogous dilution series as in the case of test A. (The resistance relates to the tolerability of Diazinon).
- the compounds according to Example 1 act in these tests against sensitive and OR resistant larvae of Boophilus microplus.
- 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 propyl, n-butyl, n-pentyl or C H OCH CH R reprelarvae, adults and eggs are evaluated after 7 days under a stereoscopic microscope and the result expressed in percentages. During the interim, the treated plants are kept in greenhouse compartments at 25C.
- the compounds according to Example 1 are active in the above test against eggs, larvae and adults of Terranchus urticae.
- the compounds according-to Example display good action against Meloidgyne Avenaria.
- R represents ethyl
- R represents propyl, n-butyl, C 'H OCH CH or n-amyl
- R and R each represents methyl or ethyl
- X and X represent hydrogen or chlo- .rine and Y represents oxygen.
- a compound according to claim 2 of the formula 4.
- a compound according to claim 2 of the formula C H O 5.
- a compound according to claim 2 of the formula 19 I 20 8.
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Abstract
Phosphoric acid phenylsulphonamide esters of the formula WHEREIN Y represents oxygen or sulphur, R represents alkyl with 1 to 5 carbon atoms, R1 represents alkyl with 1 to 5 carbon atoms, alkenyl and alkinyl each with 3 to 5 carbon atoms, alkoxyalkyl with 1 to 5 carbon atoms in each of the moieties, alkylthioalkyl with 1 to 5 carbon atoms in each of the moieties, or haloalkyl with 1 to 5 carbon atoms, R2 represents hydrogen, alkyl with 1 to 5 carbon atoms or alkenyl with 3 to 5 carbon atoms, R3 represents hydrogen and X and X1 each represents halogen or alkyl with 1 to 5 carbon atoms, or R3 represents alkyl with 1 to 5 carbon atoms and X and X1 each represents hydrogen, halogen or alkyl with 1 to 5 carbon atoms, a process for their manufacture and their use in pest control.
Description
States Patent [1 1 Drabek et a1.
[1 11 3,855,362 [451 Dec. 17, 1974 1 1 PHOSPHORIC ACID PHENYLSULPHONAMIDE ESTERS [75] Inventors: Jozef Drabek, Allschwil; Denis Varsanyi, Arlesheim, both of Switzerland [73] Assignee: Ciba-Geigy Corporation, Ardsley,
[22] Filed: Nov. 29, 1972 [21] Appl. No.: 310,507
[30] Foreign Application Priority Data OTHER PU BLICATIQNS Wagner et al., J. Med. Chem., 8(3), 1965, pages 377 to 383.
Primary I5.ran1itwr-Lorraine A. Weinberger Assistant ExaminerRichard L. Raymond Attorney, Agent, or Firm-Harry Falber; Frederick H. Rabin 5 7 ABSTRACT Phosphoric acid phenylsulphonamide esters of the formula X R R0 Y 1 SO N 2 P O I R R 8 wherein Y represents-oxygen or sulphur, R represents alkyl with 1 to 5 carbon atoms, R represents alkyl with 1 to 5 carbon atoms, 'alkenyl and alkinyl each with 3 to 5 carbon atoms, alkoxyalkyl with 1 to 5 carbon atoms in each of the moieties, alkylthioalkyl with 1 to 5 carbon atoms in each of the moieties, or haloalkyl 1 with 1 to 5 carbon atoms, R represents hydrogen, alkyl with l to 5 carbon atoms or alkenyl with 3 to 5 carbon atoms, R represents hydrogen and X and X each represents halogen or alkyl with 1 to 5 carbon atoms, or R represents alkyl with 1 to 5 carbon atoms and X and X each represents hydrogen, halogen or alkyl with 1 to 5 carbon atoms, a process for their manufacture and their use in pest control.
12 Claims, No Drawings PHOSPHORIC ACID PHENYLSULPHONAMIDE Y ESTERS I t The present invention relates to phosphoric acid phenylsulphonamide esters, a process for their manufacture and their use in pest control.
The compounds having the formula wherein Y represents oxygen or sulphur, R represents 7 alkyl with l to 5 carbon atoms, R represents alkyl with l to 5 carbon atoms, alkenyl and alkinyl each with 3 to 5 carbon atoms, alkoxyalkyl with 1 to 5 carbon atoms in each of the moieties, alkylthioalkyl with l to 5 carbon atoms in each of the moieties, or haloalkyl with l to 5 carbon atoms, R represents hydrogen, alkyl with l to 5 carbon atoms or alkenyl with 3 to 5 carbon atoms, R represents hydrogen and X and X, each represents halogen or alkyl with l to 5 carbon atoms, or R represents alkyl with l to 5 carbon atoms and X and Y R u j 1) P-Cl v H .R s j I (II) (III) Y R u P-Cl (II) (IV) Y IX R2 5a) R u SO2N X each represents hydrogen,- halogen or alkyl with 1 to 5 carbon atoms.
Halogen is to be understood as meaning fluorine,
chlorine, bromine or iodine, but in particular chlorine. Preferred haloalkyl groups with l to 5 carbon atoms The groups cited hereinabove which are possible for .R to R X and X,, may be straight-chain or branched.
Examples of such groups include: methyl, methoxy, methoxymethyl, ethyl, ethoxyethyl, ethylthioethyl, propyl, isopropyl, n-, i-, sec. and tert.butyl, n-pentyl and the isomers thereof, allyl, methallyl, n-penten-S-yl, propargyl, isobutinyl.
Preferred compounds on account of their action are those of the formula l, wherein R represents methyl or ethyl, R, represents propyl, n-butyl, n-pentyl or C H OCH CH R represents hydrogen, methyl or ethyl, R represents methyl or ethyl, X and X, each represents hydrogen or chlorine, and Y represents oxygen or sulphur.
Particularly preferred compounds, however, are those of the formula I, wherein R represents ethyl, R
represents propyl, n-butyl, C H OCH Cl-l or n-amyl,
R and R each represents methylor ethyl, X and X represent hydrogen or chlorine and Y represents oxygen. I
The compounds of the formula I can be manufactured according to methods'which are known per se:
SO N
- acid binding X I 4 agent.
reaction temperature 0-12O C MeSH reaction temperature 0-100C essary to use catalysts in the reactions, e.g. copper or copper chloride.
Processes l, 2, 3a and 3b may be carried out at normal pressure (3a at up to atmospheres absolute pressure) and in solvents or diluents. Suitable solvents or diluents are e.g., ethers and ethereal compounds, such as diethyl ether, dipropyl ether, dioxan, dimethoxyethane, tetrahydrofu'ran; amides, such as N,N-
, dialkylated carboxylic amides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, chloroform, chlorobenzene; nitriles, such as acetonitrile; dimethyl sulphoxide, ketones such as acetone, methyl ethyl ketone.
Some of the starting materials of the formulae II and V are known compounds which can be manufactured in analogous manner by known methods. The compounds of the formula I display a broad biocidal activity and are therefore suitable for combating various plant and animal pests and as plant growth regulators. Surprisingly, however, the compounds of the formula possess insecticidal and acaricidalt properties which are superior to those of know, analogous compounds, and they may be used against all development stages, e.g., eggs, larvae, pupae, nymphs and addults, of insects and representatives of the order Acarina, for example against insects of the families:
'letligonidae Tenebriomkiae Gryllidae Chrysomelidae Gryllotalpidae Bruchidag Blallidae Tineidae Reduviidae Notlindae Phyrrhoconae Lymarriidae Cimicidae Pyralidae Delphacidae Culicidae Alphididae Tipulidae Diaspididae Slamoxydae Pseudococcidae Tryperidae Scarabaeidae Muscidae Dermesridae Calliphoridae and Coccinellidae Pulicidae Acarida of the families:
Ixodidae .Argasidae Tetranychidae and Dermanyssidae.
for example, the following Z-methoxycarbamyll -methylvinyldimethylphosphate (MEVINPHOS) Dimethyll -methyl-2-( methylcarbamoyl vinylphosphate cis (MONOCROTOPHOS) 3-(dimethoxyphosphinyloxy)-N,N-dimethyl-ciscrotonamide (DlCROTOPHOS) 2-chloro-2-diethylcarbamoyl-l-methylvinyldimethylphosphate (PHOSPHAMIDON) 0,0-diethyl-O(or S)-2-(ethylthio)-ethylthiophosphate (DEMETON) S-ethylthioethyl-0,0-dimethyl-dithiophosphate (THI- OMETON) 0,0-diethyl-S-ethylmercaptomethyldithiophosphate (PHORATE) 0,0-diethyl-S-Z-ethylthio)ethyldithiophosphate SULFOTON) 0,0-dimethyl-S-2-(ethylsulphinyl)ethylthiophosphate (OXYDEMETONMETHYL) 0,0-dimethyl -S-( l ,2-dicarbethoxyethyldithiophosphate (MALATHION) 0,0,0,0-tetraethyl-S,S'-methylene-bisdithiophosphate ETHlON) O-ethyl-S,S-dipropyldithiophosphate 0,0-dimethyl-S-(N-methyl-N- formylcarbamoylmethyl)-dithiophosphate MOTHlON) 0,0-dimethyl-S-(N-methylcarbamoylmethyl)dithiophosphate (DlMETHOATE) I 0,0-dimethyl-O-p-nitrophenylthiophosphate RATHlON-METHYL) 0,0-diethyl-O-p nitrophenylthiophosphate (PARA- THlON) O-ethyl-O-pmitrophenylphenylthiophosphate (EPN) 0,0-dimethyl-O-(4-nitro-m-tolyl)thiophosphate (FENlTROTHlON) 0,0-dimethyl-O-Z,4,-5-trichlorophenylthiophosphate- (RONNEL) O-ethyl-O,2,4,5-trichlorophenylethylthiophosphate (TRICHLORONATE) (FOR- 0,0-dimethyl-O-2,5-dichloro-4-bromophenylthiophos-- phate (BROMOPHOS) 0,0-dimethyl-O-(2,5-dichloro-4-jodphenyl)- thiophosphate (JODOFENPHOS) 4-tert. butyl-2-chlorophenyl-N-methyl-O- methylamidophosphate (CRUFOMATE) 0,0-dimethyl-O-(3-methyl-4-methylmercaptophenyl)- thiophosphate (FENTHION) lsopropylarnino-O-ethyl-O'(4-methylmercapto-3- methylphenyl)-phosphate 0,0-diethyl-O-p-(methylsulphinyl)phenylthiophosphate (FENSULFOTHION) O-p-(dimethylsulphamid0)phenyl-0,0-dimethylthiophosphate (FAMPHUR) 0,0,0,O'-tetramethyl-0,0'-thiodi-p-phenylenethiophosphate O-ethyl-S-phenyl-ethyldithiophosphate 0,0-dimethyl-O-( oz-methylbenzyl 3-hydroxycrotonyl phosphate 2-chloro-1-(2,4-dichl0rophenyl)vinyldiethylphosphate (CHLORFENVINPHOS) dimethylphosphate O-[2-chloro l-(2,5-dichlorophenyl)]vinyl-0,0-
diethylthiophosphate Phenylglyoxylonitriloxium-0,0-diethylthiophosphate PHOXIM) 0,0-diethyl-O-(3-chloro-4-methyl-2-oxo-2-H-I- 2-( l-methoxy-2-propoxy)pheny-N-methylcarbamate 9 2-( 1,3-dioxolan-2-yl )phenyl-N,N-dimethylcarbamate 2-( 1,3-dithiolan-2-yl)-N,N-dimethylcarbamate 2-( l,3-dithiolan-2yl)phenyl-N,N-dimethylcarbamate 2-isopropoxyphenyl-N-methylcarbamate (APROCARB) 2-(Z-propinyloxy)phenyl-N-methylcarbamate 3-( 2-propinyloxy )phenyl-N-methylcarbamate Z-dimethylaminophenyl-N-methylcarbamate 2-diallylaminophenyl-N-methylcarbamate 4-diallylamino-3,5-xylyl-N-methylcarbamate LYXlCARB) 4-benzothienyl-N-methylcarbamate 2,3-dihydro-2-methyl-7-benzofuranyl-N- methylcarbamate 3-methyll -phenylpyrazol-5-yl N,N-dimethylcarbamate l-isopropyl-3-methylpyrazol-5-yl-N,N,-dimethylcarbamate (ISOLAN) 2-dimethylamino-5,6-di methylpyrimidine-4-yl-N,N,- dimethyl-carbamate 3-methyl-4-dimethylaminomethyleneiminophenyl-N- methylcarbamate 3-dimethylamino-methyleneiminophenyl-N- methylcarbamate (FORMETANATE) and their salts l-methylthio-ethylimino-N-methylcarbamate (ME-- THOMYL) 2-methylcarbamoyloxirnino-l ,3-dithiolane 5-methyl-2-methylcarbamoyloximino-1,3-oxythiolane 2-( lbutin-3-yl-oxy)phenyl-N-methylcarbamate l-dimethylcarbamyl-1methylthio-O-methylcarbamylformoxime l-( 2-cyanoethylthio )-O-methylcarbamylacetaldoxime. 1 -methylthio-O-carbamyl-acetaldoxime O-( 3-sec.butylphenyl)-N-phenylthio-N- methylcarbamate 2,5-dimethyl-l ,3-dithioland-2-(O-methylcarbamyl)- aldoxime 0-2-diphenyl-N-methylcarbamate 2-(N-methylcarbamyl-bximino)-3chlorobicyclo[2.2.1]heptane 2-(N-methylcarbamyl-oximino)-bicyclo[2.2. l ]heptane 3-isopropylphenyl-N-methyl-N-chloroacetylcarbamate 2[dipropargylamino]-phenyl-N-methylcarbamate 4[dipropargylamino ]-3-tolyl-N-methylcarbamate 4[dipropargylamino]-3,5-xylyl-N-methylcarbamate 2-[allyl-isopropylamino]-phenyl-N-methylcarbamate 3-[ally-isopropylamino]-pheny-N-methylcarbamate Chlorinated Hydrocarbons 'y-hexachlorocyclohexane lGAMMEXANE; LlNDAN; yHCH] l,2,4,5,6,7,8,8-octachloro-3a,4,7,7atetrahydro-4,7-
' methylen-indane [CHLORDAN] l,4,5,6,7,8,8-heptachloro,3a,4,7,7a-tetrahydro-4,7- methylen-indane [HEPTACHLOR] l,2,3,4,10,lO-hexachloro-l,4,4a,5,8a-hexahydroendol ,4-exo-5,S-dimethanonaphthalene [ALDRIN] 1,2,3 ,4, l 0, l O-heXachloro-6,7-epoxyl ,4,4a5,6,7,8,8a-
oxtahydro-exo-l ,4-endo-5 ,Sdimethanonaphthalene [DIFLORIN] l,2,3,4,1O,IO-hexachloro-SJ-epoxy l,4,4a,5,6,7,8,8aoctyhydro-endo-endo-S,8-dimethanonaphthalene [EN- N] The active substances of the formula I are also suitable for combating representatives of the division Thallophyta, e.g., viruses, bacteria and fungi. They thus possess fungicidal properties against phytophathogenic fungi on various cultivated plants, such as cereals, maize, rice, vegetables, ornamental plants, fruit trees, vines, farms products, etc.
With the new active substances it is possible to con trol or destroy fungi occurring onfruit, blossom, leaves,
stems, tubers and roots, and from which parts of plants which grow later then also remain free. The active sub stances of theformula I are active in particular against phytopahtogenic fungi belonging to the following classes: Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Denteromycetes.
In addition, the new active substance can also be used for treating seeds, fruits, tubers etc., and the protecting them from fungus infections, for example from smut fungi of all kinds, such as Ustilaginales, e.g. Ustilago, Tilletia, Urocystis, Turbicinia and Phoma types.
In addition to the above cited acaricides and insecti-- cides, it is also possible to admix' the active substances of the formula I with, for example, batericides, fungi- I static agents, baceteriostatic agents, nematocides andthe activity spectrum: dodecylquanidine acetate (DODlNE) (CHLOR- N'-dichlorofluoromethylthio-N,N-dimethyl-N'- phenylsulfamide (DICHLOFLUANID) O-ethyl-S-benzyl-phenyldithiophosphate 0,0-diethyl-S-benzyl-thiolphosphate disodium-ethylene-1,2-bis-dithiocarbamate (NABAM) zinc-ethylenel ,2-bis-dithiocarbamate (ZINEB) manganese-ethylene-l ,2-bis-dithiocarbamate meric) (MANEB) tetramethyliuramdisulfide (THIRAM) l -oxy-3-acetyl-6-methyl-cyclohexene-( 5 )dione-( 2,4) (DEHYDROACETIC ACID) 8-hydroxyquinoline (8-QUINOLINOL) 3O 2-dimethylamino-6-methyl 5-n-butyl-4-hydroxyprimidine methyl-N-benzimidazole-2yl-N-(butylcarbamoyl)carbamate (BENOMYL) 2-ethylamino-6-methyl-5n-butyl-4-hydroxypyrimidine 2,3-dicyano-1,4-dithia-anthraquinone (DITHIANON 2-(4-thiazolyl)-benzimidazole 3 ,S-dimethyltetrahydro-l ,3 ,5'-thiadiazine-2-thione (DAZOMET) 2,3-dihydro-5-carboxanilido-6-inethyll ,4-oxathine 40 pentachlorobenzyl alcohol.-
Furthermore, the compounds of the formula I are suitable for combating plant pathogenic nematodes.
The compounds of the formula I may be used as pure active substance or together with suitable carriers and- /or additives. Suitable carriers and additives can be solid or liquid and correspond to the substances conventionally used in formulation technique such, for example, as solvents dispersants, wetting agents, adhesives, thickeners, binders and/or fertilisers.
'For application, the compounds of the formula I may be processed to dusts, emulsion concentrates, granules, dispersions, sprays, to solutions, or suspensions in the conventional formulation which is commonly employed in application technology. Mention may also be made of cattle clips and spray races," in which aqueous preparations are used.
The agents according'to the invention are manufactured in known manner by intimately mixing and/or grinding active substances of the formula I with the suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active substances. The active substances may take and be used in the following forms:
Solid forms:
Dusts, tracking agents, granules, coated granules, impregnated granules and homogeneous granules.
Liquid forms:
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. Suitable carriers are, for example, kaolin, talcum, bo- Ius, loess, chalk, limestone, ground limestone, attaclay, dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminium silicates (feldspar and mica), calcium and magnesium sulphates, magnesium oxide, ground synthetic materials, fertilisers, for example ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, ground vegetable products, such as corn meal, bark dust, sawdust, nutshell meal, cellulose powder, residues of plant extractions, activated charcoal etc. These substances can either be used alone or in admixture with one another.
Granules can be very easily manufactured by dissolving an active substance of the formula I in an organic solvent and applying the resulting solution to a granulated material, for example attapulgite, S10 granicalci um, bentonite etc. and then evaporatingthe solvent. v
Polymer granules can also be manufactured by mixing the active substances of the formula I with polymerisable compounds (urea/formaldehyde; dicyandiamide/formaldehyde; melamine/formaldehyde or others), whereupon a mild polymerisation 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) which have a specific surface area and a favourable predeterminable adsorption/desorption ratio, with the active substances, for example in the form of their solutions (in a low boiling solvent) and to remove the solvent. Polymer granules of this kind in the form of microgranules having a bulk density of 300 g/litre to 600 g/litre can also be manufactured with the aid of atomisers. The dusting can be carried out from aircraft over extensive areas of cultures of useful plants.
It is also possible to obtain granules by compacting the carrier with the active substance and carriers and subsequently comminuting the product.-
To these mixtures can also be added additives which stabilize the active substance and/or non-ionic, anionic and cationic surface active substances, which, for example, improve the adhesion of the active ingredients on plants or parts of plants (adhesives and agglutinants) and/or ensure a better wettability (wetting agents) and a dispersibility (dispersing agents). Examples of suitable adhesives are the following: olein/chalk mixture, cellulose derivates (methyl cellulose, carboxy methyl cellulose), hydroxyethyl glycol ethers of monoalkyl and dialkyl phenols having 5 to 15 ethylene oxide 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), fatty alcohol polyethylene glycol ethers having 5 to 20 ethylene oxide radicals per molecule and 8 to 18 carbon atoms in the fatty alcohol moi ety, condensation products of ethylene oxide/propylene oxide, polyvinyl pyrrolidones, polyvinyl alcohols, condensation products of urea and formaldehyde, and also latex products.
The water-dispersible concentrates of the active substance, i.e., wettable powders, pastes and emulsifiable concentrates, are agents which can be diluted with water to any concentration desired. They consist of active substance, carrier, optionally additives which stabilize the active substance, surface-active substanceand anti-foam agents and, optionally, solvents.
W'ettable powders and pastes are obtained by mixing and grinding the active substances with dispersing agents and pulverulentcarriers in suitable apparatusuntil homogeneity is attained. Suitable carriers are, for example, those mentioned for the solid forms of application. In some cases it is advantageous to use mixtures of different carriers. As dispersing agents there can be used, for example, condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, as well as alkali, ammonium and alkaline earth metal salts of lignin sulfonic acid, in addition, a]-
kylaryl sulfonates, alkali and alkaline-earth metal salts of dibutyl naphthalene sulfonic acid, fatty alcohol sulfates such as salts 'of sulfated hexadecanols, hep- 'tadecanols, octadecanols, and salts of sulfated fatty alcohol glycol ethers, the sodium salt of oleoyl ethionate, the sodium salt of oleoyl methyl tauride, ditertiary acetylene glycols, dialkyl fatty acid alkali and alkaline earth metal salts.
Suitable anti-foam agents are silicones. g
The active substances are mixed, ground, sieved and strained with the additives cited hereinabove in such a. manner that, in wettable powders, the solid particle size of from 0.02 to 0.04 and in pastes, of 0.03 is notexdilauryl ammonium chloride and ceeded. To produce emulsifiable concentrates and pastes, dispersing agents such as those cited above,-organic solvents and water are used. Examples of suitable solvents are: alcohols, benzene, xylene, toluene dimethyl sulfoxide, and mineral oil fractions boiling between 120 and 350C. The solvents must be practically odourless, not phytotoxic, inert to the active substances.
Furthermore, the agents according to the invention can be applied in the form of solutions. For this purpose the active substance or several active substances of the general formula I are dissolved in suitableorganic solvents, mixtures of solvents or in water. Aliphatic and aromatic hydrocarbons, chlorinated derivatives thereof, alkyl naphthalenes, and mineral oils singly or in admixture with each other, can be used as organic solvents.
The content of active substance in the above described agents is between 0.1 to 95 percent, in which connection it should be mentioned that, in the case of application from aircraft or some other suitable means of application, it is possible to use concentrations of up to 99.5 percent or even pure active substance.
The active substances of the formula I can, for example, be formulated as follows: Dusts The following substances are used to manufacture (a) a 5 percent and (b) a 2 percent dust: v
a. 5 parts of active substance 95 parts of talcum b. 2 parts of active substance 1 part of highly disperse silica 97 parts of talcum. The active substances are mixed with the carriers and ground. Granules The following substances are used to produce 5% granules:
5 parts of active substance,
0.25 parts of epichlorohydrin,
0.25 parts of cetylpolyglycol ether,
3.50 parts of polyethylene glycol,
91 parts of kaolin (particle size 0.3 0.8 mm);
The activesubstance ismixed with epichlorohydrin and dissolved with 6 parts ofacetone; the polyethylene glycol and cetyl polyglycol ether are then added. The thus obtained solution is sprayed on to kaolin, and the acetone subsequently evaporated in vacuo.
Wettable powder The following constituents are used for. the preparation of (a) a 40 percent, (b) and (d) a 10 percent wettable powder:
a. 40 parts of active substance,
5 parts of sodium lignin sulphonate,
1 part of sodium dibutyl-naphthalene sulphonate,
54 parts of silica acid.
b. 25 parts of active substance,
4.5 parts of calcium lignin sulphonate 1.9 partsof Champagne chalk/hydrox'yethyl cellulose mixture (1:1),
-'l.5 parts of sodium dibutyl naphthalene sulphonate',
parts of silica acid,
19.5 parts of Champagne chalk,
28.1 parts of kaolin.
c. 25 parts of active substance,
2.5 parts of -isooctylphenoxy-polyoxyethyleneethanol,
1,7 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1),
8.3 parts of sodium aluminium silicate,
16.5 parts of kieselguhr,
46 parts of kaolin.
d. 10 parts of active substance,
3 parts of a mixture'of the sodium salts of saturated fatty alcohol sulphates,
5 parts of naphthalen condensate,
82 parts of kaolin.
The active substances are intimately mixed, in suit able mixers, with the additives, the mixture being then ground in the appropriate mills and rollers. Wettable powder are obtained which can be diluted with water to give suspensions of any desired concentration. Emulsifiable concentrates:
The following substances are used to produce (a) a 10 percent and (b) a 25 percentemu'lsifiable concentrate:
. From these concentrates it is possible to produce, by dilution with water, emulsion of any desired concentration.
c) a 25 percent and sulphonic acid/formaldehyde Spray:
The following constituents are used to prepare a percent spray:
5 parts of active substance,
1 part of epichlorohydrin,
94 parts of benzine (boiling limits 160 190C).
EXAMPLE 1 play ingest poison action against Spodoplera litoratis and Leptinotarsa decemlineala. 8. Systemic insecticidal action To determine the systemic action, rooted bean plants (Viciafabae) are put into a 0.01 percent aqueous active substance solution (obtained from a 10 percent emulsifiable concentrate). After 24 hours, aphids (Aphis fabae) are placed on the parts of the plant above the soil. The aphids are protected from contact and gas action by means ofa special device. The test is carried out at 24C and 70 percent relative humidity. In the above tests the compounds according to Example I displayed good insecticidal ingest poison action and systemic insecticidal action.
EXAMPLE 3 Action against Chilo suppressalis Six rice plants at a time of the variety Caloro were transplated into plastic pots (diameter at the top 17 cm) and reared to a height of about 60 cm. Infestation with Chilo suppressalis larvae (L 3-4 mm long) took place 2 days after application of the active substance in The following compounds are also manufactured in granule form to the paddy water (rate of application:
analogous manner:
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 homogeneously mixed substance so that there resulted a rate of application of 8 kg of active substance per hectare.
Young zucchetti plants (Cucumis peop) were put into plastic pots with the treated soil (3 plants per pot; diameter of pot 7 cm). Each pot was infected immediately aterwards with 5 Aulocophora femoralis and Pachmoda or Chortiphilia larvae. The control was carried out 4, 8, l6 and 32 days after depositing the larvae.
' At -100 percent kill after the first control, a fresh infestation with 5 larvae each was carried out in the ple I displayed action against Aulacophora fermralis,-
Pachmoda and Chlortophila larvae.
EXAMPLE Action against ticks A. Rhicephalus bursa.
In each of two test series 5 adult ticks and 50 tick larvae are counted into a glass tube and immersed for l to 2 minutes in 2 ml of an aqueous emulsion from an amulsion series each containing 100, 10, l and 0.1 ppm of test substance. The tube is then sealed with a standardised cotton wool plug and placed on its head, so that the active substance emulsion can be adsorbed by the cotton -wool.
In the case of the adults evaluation takes place after 2 weeks, and in that of the larvae after 2 days. Each test is repeated twice.
The compounds according to Example 1 act in the above test against adults and larvae of Rhicephalus bursa. B. Boophilus microplus (larvae) Tests are carried out in each case with 20 OP- sensitive larvae using analogous dilution series as in the case of test A. (The resistance relates to the tolerability of Diazinon).
The compounds according to Example 1 act in these tests against sensitive and OR resistant larvae of Boophilus microplus.
EXAMPLE 6 Acaracidal 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 propyl, n-butyl, n-pentyl or C H OCH CH R reprelarvae, adults and eggs are evaluated after 7 days under a stereoscopic microscope and the result expressed in percentages. During the interim, the treated plants are kept in greenhouse compartments at 25C.
The compounds according to Example 1 are active in the above test against eggs, larvae and adults of Terranchus urticae.
EXAMPLE 7 In order to assess the nematocidal action, the galls.
present on the roots are counted 28 days after planting and sowing. The compounds according-to Example display good action against Meloidgyne Avenaria.
We claim: 1. A compound of the formula wherein R represents methyl or ethyl, R represents sents hydrogen, methyl or ethyl, R represents 'methyl or ethyl, X and X, each represents hydrogen or chlorine, and Y represents oxygen or sulphur.
2. Compounds according to claim 1, wherein R represents ethyl, R represents propyl, n-butyl, C 'H OCH CH or n-amyl, R and R each represents methyl or ethyl, X and X represent hydrogen or chlo- .rine and Y represents oxygen.
3. A compound according to claim 2 of the formula 4. A compound according to claim 2 of the formula C H O 5. A compound according, to claim 2 of the formula $0 M CH5 2 7. A compound according to claim 2 of the formula 19 I 20 8. A compound according to claim 1 of the formula 11. A compound according to claim 1 of the formula n C H S ll Cl 3 7 S c H P SO N(CH (MCBRIS I 2 5, C1 P-O -SO MCIL 9. a compound according to claim 1 of the formula S (n) C H S II 12. A compound according to claim I of the formula P- so N(C H i c H 2 2 5 2 S 10. A compound according to claim 1 of the formula 2 5 llZ 3L SO N(CH 0 H
Claims (12)
1. A COMPOUND OF THE FORMULA
2. Compounds according to claim 1, wherein R represents ethyl, R1 represents propyl, n-butyl, C2H5OCH2CH2- or n-amyl, R2 and R3 each represents methyl or ethyl, X and X1 represent hydrogen or chlorine and Y represents oxygen.
3. A compound according to claim 2 of the formula
4. A compound according to claim 2 of the formula
5. A compound according to claim 2 of the formula
6. A compound according to claim 2 of the formula
7. A compound according to claim 2 of the formula
8. A compound according to claim 1 of the formula
9. a compound according to claim 1 of the formula
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
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/508,592 US3934010A (en) | 1971-12-03 | 1974-09-23 | Insecticidal composition and method utilizing phosphoric acid phenylsulphonamide esters |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1761971A CH564908A5 (en) | 1971-12-03 | 1971-12-03 | (di)thiophosphoric acid esters - with biocidal activity |
CH1386972A CH575211A5 (en) | 1972-09-22 | 1972-09-22 | (di)thiophosphoric acid esters - with biocidal activity |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/508,592 Division US3934010A (en) | 1971-12-03 | 1974-09-23 | Insecticidal composition and method utilizing phosphoric acid phenylsulphonamide esters |
Publications (1)
Publication Number | Publication Date |
---|---|
US3855362A true US3855362A (en) | 1974-12-17 |
Family
ID=25713234
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00310507A Expired - Lifetime US3855362A (en) | 1971-12-03 | 1972-11-29 | Phosphoric acid phenylsulphonamide esters |
Country Status (14)
Country | Link |
---|---|
US (1) | US3855362A (en) |
JP (1) | JPS4862940A (en) |
BE (1) | BE792185A (en) |
CA (1) | CA1050563A (en) |
DD (1) | DD108449A5 (en) |
DE (1) | DE2258751A1 (en) |
EG (1) | EG10757A (en) |
ES (1) | ES409218A1 (en) |
FR (1) | FR2162161B1 (en) |
GB (1) | GB1398584A (en) |
HU (1) | HU166825B (en) |
IL (1) | IL40681A (en) |
IT (1) | IT983177B (en) |
NL (1) | NL7215273A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4147781A (en) * | 1977-11-25 | 1979-04-03 | Rohm And Haas Company | O,s-dialkyl o-benzamidophenyl phosphorothiolates and phosphorodithioates and pesticidal methods |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3309371A (en) * | 1963-10-16 | 1967-03-14 | American Cyanamid Co | Organophosphorothioate compounds and method of preparing same |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1284753A (en) * | 1960-02-29 | 1962-02-16 | American Cyanamid Co | Organic thiophosphates and process for their preparation |
-
0
- BE BE792185D patent/BE792185A/en unknown
-
1972
- 1972-10-27 IL IL40681A patent/IL40681A/en unknown
- 1972-11-08 CA CA155,924A patent/CA1050563A/en not_active Expired
- 1972-11-10 NL NL7215273A patent/NL7215273A/xx unknown
- 1972-11-29 US US00310507A patent/US3855362A/en not_active Expired - Lifetime
- 1972-11-30 IT IT32361/72A patent/IT983177B/en active
- 1972-11-30 DE DE19722258751 patent/DE2258751A1/en not_active Ceased
- 1972-11-30 DD DD167211A patent/DD108449A5/xx unknown
- 1972-11-30 EG EG493/72A patent/EG10757A/en active
- 1972-12-01 HU HUCI1309A patent/HU166825B/hu unknown
- 1972-12-01 GB GB5559072A patent/GB1398584A/en not_active Expired
- 1972-12-01 FR FR7242796A patent/FR2162161B1/fr not_active Expired
- 1972-12-02 ES ES409218A patent/ES409218A1/en not_active Expired
- 1972-12-02 JP JP47121117A patent/JPS4862940A/ja active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3309371A (en) * | 1963-10-16 | 1967-03-14 | American Cyanamid Co | Organophosphorothioate compounds and method of preparing same |
Non-Patent Citations (1)
Title |
---|
Wagner et al., J. Med. Chem., 8(3), 1965, pages 377 to 383. * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4147781A (en) * | 1977-11-25 | 1979-04-03 | Rohm And Haas Company | O,s-dialkyl o-benzamidophenyl phosphorothiolates and phosphorodithioates and pesticidal methods |
Also Published As
Publication number | Publication date |
---|---|
IT983177B (en) | 1974-10-31 |
IL40681A (en) | 1975-12-31 |
DE2258751A1 (en) | 1973-06-07 |
FR2162161B1 (en) | 1976-01-30 |
IL40681A0 (en) | 1972-12-29 |
DD108449A5 (en) | 1974-09-20 |
EG10757A (en) | 1976-05-31 |
HU166825B (en) | 1975-06-28 |
NL7215273A (en) | 1973-06-05 |
JPS4862940A (en) | 1973-09-01 |
BE792185A (en) | 1973-06-01 |
CA1050563A (en) | 1979-03-13 |
ES409218A1 (en) | 1975-12-16 |
FR2162161A1 (en) | 1973-07-13 |
GB1398584A (en) | 1975-06-25 |
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