US3142614A - Polyvalent organo-lead fungicide - Google Patents
Polyvalent organo-lead fungicide Download PDFInfo
- Publication number
- US3142614A US3142614A US122660A US12266061A US3142614A US 3142614 A US3142614 A US 3142614A US 122660 A US122660 A US 122660A US 12266061 A US12266061 A US 12266061A US 3142614 A US3142614 A US 3142614A
- Authority
- US
- United States
- Prior art keywords
- salt
- fungicides
- fungicidal
- organolead
- ingredient
- 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
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 22
- 239000000417 fungicide Substances 0.000 title description 20
- 239000000203 mixture Substances 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 31
- 239000004480 active ingredient Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 description 19
- 238000009472 formulation Methods 0.000 description 18
- 150000001450 anions Chemical class 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 12
- 241000233866 Fungi Species 0.000 description 11
- 230000035784 germination Effects 0.000 description 11
- 230000003750 conditioning effect Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 8
- 229940068492 thiosalicylate Drugs 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- -1 di-(2,5-diethylphenyl)lead Chemical compound 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- CBTNQWNORLDNTB-UHFFFAOYSA-N triethyllead Chemical compound CC[Pb](CC)CC CBTNQWNORLDNTB-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 231100000674 Phytotoxicity Toxicity 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- XKNKHVGWJDPIRJ-UHFFFAOYSA-M arsanilate(1-) Chemical compound NC1=CC=C([As](O)([O-])=O)C=C1 XKNKHVGWJDPIRJ-UHFFFAOYSA-M 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- JUUVKOUSGRIGLL-UHFFFAOYSA-N diethyllead Chemical compound CC[Pb]CC JUUVKOUSGRIGLL-UHFFFAOYSA-N 0.000 description 5
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 5
- 239000012895 dilution Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- XKSLEJLZTDEXGB-UHFFFAOYSA-N dimethyllead Chemical compound C[Pb]C XKSLEJLZTDEXGB-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 231100000208 phytotoxic Toxicity 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 125000001624 naphthyl group Chemical class 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 2
- LMDKALUFKHCRFQ-UHFFFAOYSA-M tributylplumbyl acetate Chemical compound CCCC[Pb](CCCC)(CCCC)OC(C)=O LMDKALUFKHCRFQ-UHFFFAOYSA-M 0.000 description 2
- SBXVIQINPJYMHB-UHFFFAOYSA-N triphenyllead Chemical compound C1=CC=CC=C1[Pb](C=1C=CC=CC=1)C1=CC=CC=C1 SBXVIQINPJYMHB-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241001518731 Monilinia fructicola Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- XKNKHVGWJDPIRJ-UHFFFAOYSA-N arsanilic acid Chemical compound NC1=CC=C([As](O)(O)=O)C=C1 XKNKHVGWJDPIRJ-UHFFFAOYSA-N 0.000 description 1
- 229950002705 arsanilic acid Drugs 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XBBHFQNIEJGGIG-UHFFFAOYSA-N dibutyllead Chemical compound CCCC[Pb]CCCC XBBHFQNIEJGGIG-UHFFFAOYSA-N 0.000 description 1
- 229940120124 dichloroacetate Drugs 0.000 description 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- VUHZYDMWLAVOGY-UHFFFAOYSA-N dioctyllead Chemical compound CCCCCCCC[Pb]CCCCCCCC VUHZYDMWLAVOGY-UHFFFAOYSA-N 0.000 description 1
- VITHRHRYZSQDDQ-UHFFFAOYSA-N diphenyllead Chemical compound C=1C=CC=CC=1[Pb]C1=CC=CC=C1 VITHRHRYZSQDDQ-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- BPDDFRMYIQRZHQ-UHFFFAOYSA-N ethyl 2,4-diphenyl-1h-imidazole-5-carboxylate Chemical compound CCOC(=O)C=1NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 BPDDFRMYIQRZHQ-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 150000002576 ketones Chemical class 0.000 description 1
- SOIILYZAUQRZDI-UHFFFAOYSA-L lead(2+) 2,2,2-triphenylacetate Chemical compound [Pb+2].C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)[O-])C1=CC=CC=C1.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)[O-])C1=CC=CC=C1 SOIILYZAUQRZDI-UHFFFAOYSA-L 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- TUGRZABPBFMBSA-UHFFFAOYSA-N tetrapentylplumbane Chemical compound CCCCC[Pb](CCCCC)(CCCCC)CCCCC TUGRZABPBFMBSA-UHFFFAOYSA-N 0.000 description 1
- WBJSMHDYLOJVKC-UHFFFAOYSA-N tetraphenyllead Chemical compound C1=CC=CC=C1[Pb](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WBJSMHDYLOJVKC-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- KXBADNRYDZGNCW-UHFFFAOYSA-N tributyllead Chemical compound CCCC[Pb](CCCC)CCCC KXBADNRYDZGNCW-UHFFFAOYSA-N 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ZFNWDVUSZNZYLD-UHFFFAOYSA-M triethylplumbyl acetate Chemical compound CC[Pb](CC)(CC)OC(C)=O ZFNWDVUSZNZYLD-UHFFFAOYSA-M 0.000 description 1
- WKZSIFJHJCVUPZ-UHFFFAOYSA-N trimethyllead Chemical compound C[Pb](C)C WKZSIFJHJCVUPZ-UHFFFAOYSA-N 0.000 description 1
- QPVPLZOVPDMOEL-UHFFFAOYSA-N tripropyllead Chemical compound CCC[Pb](CCC)CCC QPVPLZOVPDMOEL-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002569 water oil cream Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/24—Lead compounds
Definitions
- An object of this invention is to provide new fungicidal compositions.
- a further object is to provide new fungicidal compositions comprising conditioning agents and certain organolead salts as described herein.
- Still another object is, to provide new means and methods for combatting fungi.
- fungicidal compositions comprising a conditioning agent and, as a principal active fungicidal ingredient, a particular type of organolead salt containing 2 to 3 organo groups.
- organolead salts in question have the formula Ri Ra Pb It: Anion whereinR, and R are alkyl or aryl groups, wherein R is alkyl, aryl or Anion.
- Anion is a member of the group consisting of chlorophenate anions, arenesulfonamide a nions, thiosal igl ate anion, a ge gge anion, haloaeetate z 1 n i qns, dihydrogen phgsphg te agion, and arsanilate ant on.
- R R and R are not necessarily the same.
- the alkyl groups each cort tairuip to about 8- carbon atoms.
- the aryl grb'fi'p's fi fef'e'i' a blf comm' a'bout 12 carbonmomrand arephenyl, alkyl-substituted phenyl, naphthyl and alkyl-substituted naphthyl groups.
- the dialkyllead and trialkyllead salts of the foregoing formula have greater potency against most common fungi than do the above diarylleadand triaryllead salts and for this reason these alkyllead salts can and preferably are used at lower concentrations in combatting or controlling fungi especially those that infest vegetation. it will be a simple matter in the light of this description to determine the optimum concentration of my fungicides for all intended uses and applications.
- the chlorophenate anions of my novel fungicidal compositions can contain one, two. and pre erably, three, four or five chlorine atoms.
- the nucleus of the phenoxy group can be additionally substituted with loweralkyl wows-preferably methyl, ethyl. propyl or butyl groupswhen there are less than five chlorine substituents on the ring.
- Particularly effective are the diand triorganolead pentachlorophenates.
- Illustrative examples of the organolead chlorophenate salts used as fungicides pur- V suant to this invention include triethyllead chlorophenate (0-, m-, p-chloro isomers, or mixtures of these).
- triethyllead-2,4-dichlorophenate the triethyllcad tetrachlorophenates, triethyllead pentaehlorophenate, diethyllead di- (2,5-dichlorophenate). dimethyllead di-t2.4,5-trichlorophenate).
- the arenesulfonamide anions of the present fungicides preferably contain from 6 to about it) carbon atoms in the arene group.
- these compounds are triethyllcad-p-tolucnc sulfonamidc, diethyllead di-(p-toluene sulfonamide), tripropyllead benzene sulfonamide, trihexyllead-p-cumene sulfonamide, dioctyllead di-(2,4-xylene sulfonamide), trixyllead-p-toluene sulfonamide (mixed xylyl isomers).
- diphcnyllead di-(benzene sulfonamide), and the like diphcnyllead di-(benzene sulfonamide), and the like.
- the diand triorangolead arenesulfonamides are preferred for use in this invention because of their relatively low phytotoxicity against such common crops as cotton and soybeans.
- my diand triorganolead thiosalicylate fungicides include triethyllead thiosalicylate, triheptyllead thiosalicylate, dimethyllead di-(thiosalicylate), methylphcriyllead di-(thiosalicylate), tri-m-tolyllead thiosalicylate. di-2 .5-xylyllead dHthiosalicylate), and the like.
- a preferred feature of these compounds is their relatively, low phytotoxicity against such crops as cucumbers and soybeans.
- my diand triorganolead acetate fungicides are triethyllead acetate trimethyllead acctate..diethyllead diace ae, l u ead diacetate, tributyllead acetate, triphenyllead acetate, diphenyllead diacetate, di-(2,5-diethylphenyl)lead diacctate, and the like.
- An advantageous and preferred characteristic of these diand triorganolead acetates is their relatively low phytotoxicity against such abundant crops as corn and wheat. Moreover. these compounds can be readily prepared at relatively low cost. and these factors, together with their considerable fungicidal potency render the acetates especially preferred for use in this invention.
- the haloaeetate anions of my novel fungicidal compositions can contain 1, 2 or 3 halogen atoms in the acetate radical, these halogens being bromine. iodine, and preferably chlorine or fluorine. Mixtures of these halogen atoms can also be present.
- Specific examples of these fungicides include triethyllead trichloroacetate, triethyllead trifluoroacetate, diethyllead di-(monochloroacetate), dimethyllead di-(monochloroacetate). tributyllead dichloroacetate. trihexyllcad dichl'orolluoroacetate.
- triphenyllead trichloroacctatc dicumenyllead di-(monofluoroacetate), phcnyldiethyllead tribromoacctate, diamyllead di- (monoiodoacetatc). and the like. These compounds are preferred for use in this invention because of their relatively low phytotoxicity against such plant species as soybeans.
- my diand triorganolead dihydrogen phosphate fungicides include triethyllead dihydrogen phosphate. trioctyllead dihydrogen phosphate. tripheriyllead dihydrogen phosphate. diethyllead bis-(dihydrogen phosphate). di-o-tolyllead his-(dihydrogen phosphate), oetyldimethyllead dihydrogen phosphate. and the like.
- Exemplary of my diand triorganolead arsanilate fudgicides are tricthyllcad arsanilate, tri-sec-butyl arsanilate. triphcnyllead arsanilate, triamyllead arsaniiate, dimethyllead diarsanilate. di-2.4-xylyllead diarsanilate. phenyl-ptolyllead diarsanilatc. and the like.
- An advantage of these compounds is their relatively low phytotoxicity as regards such crops as soybeans.
- the conditioning agents with which I admix my active fungicidal ingredients are of the type known to the art as substantially inert fungicidal adjuvants. These comprise a dispersant and a surface active agent. The purpose of these materials is to extend the active fungicidal ingredient to insure its efficacious penetration into or application onto the locus being treated and to adapt the active fungicidal ingredients for ready and efficient application to pests and to the loci of the fungi using conventional equipment.
- such formulations comprise both the liquid and solid types as well as the Aerosol" type of formulation.
- the liquid type of formulation can have water, an organic solvent, an oil-' water emulsion and the like as the conditioning agent.
- the liquid ingredient of the formulation may further contain a surface active agent such as a detergent, a soap or other wetting agent'
- a surface active agent such as a detergent, a soap or other wetting agent'
- the term conditioning agent include solid carriers such as talc. pyrophyllite, Attaclay, kieselguhr, chalk, diatomaceous earth, and the like; and various mineral powders such as calcium carbonate and the like which act as a dispersant, as a carrier, and in some instances perform the function of a surface active agent.
- solid conditioning agents include those known as wettable powders. In general these wettable powders include the active ingredient, a surface active agent and an inert carrier such as soybean flour, sulfur, calcium oxide, mica, talc, humus and the like.
- Such formulations provide the advantage of permitting storage and transportation of the pesticides in readily handled form and permit further dilution by simple admixture with water to provide finished liquid formulations at the time of application.
- formulations which comprise my active ingredient in combination with a conditioning agent provide liquid. solid and aerosol formulations in a.,form
- the liquid compositions either solutions or dispe'sions, frequently contain a surface active dispersing agent in amount sufficient to render the composition readily dispersable in water for aqueous spray application.
- the solid formulations also frequently contain a surface active dispersing agent in amount sufficient to impart water dispersibility to the compositions. When dust application is desired a surface active dispersing agent can be omitted. In this case the formulation will still contain a solid carrier, extender or diluent as conditioning agent.
- the surface active dispersing agents referred to herein are sometimes known as wetting, dispersing or penetrating agents. They are agents which cause the formulations to be easily dispersed in water. They can be of the anionic, cationic or non-ionic type and include salts of long chain fatty. acids, sulfonated oilsboth vegetable ..nd animalpetroleum oils, sulfates of long chain alco- 'hols, phosphates of long chain alcohols, various polyethylene oxides and condensation products of ethylene oxide with alcohols and phenols, quaternary ammonium salts and the like. The surface active agent will usually be present to the extent of 0.1 to 5 percent of the formulation.
- the active ingredients can also be dispersed or suspended in various organic solvents such as alcohols. ketones, hydrocarbons, petroleum cuts such as kerosene, dimethylformamide and the like.
- a surface active dispersing agent is usually present to provide ready dispersibility with water.
- I mix 50 parts of tributyllead acetate with 50 parts of diatomaceous earth and 3 parts of sodium lauryl sulfate and then grind the mixture to obtain a wettable powder formulation suitable for dilution with water. I also mix 30 parts of diisopropyllead di-(pentachlorophenate) with 500 parts of fuller's earth to obtain a dust formulation suitable for application.
- compositions comprising active ingredients of this invention together with conditioning agents are prepared by similar means and ha e in general make-ups similar to those given above.
- the fungicidal effectiveness of my compounds can be demonstrated by the following test.
- a minus sign indicates the average results of two tests where the determinations varied by one rank. For example, a rating of AA shows that in one determination the compound had an AA rating while in another it had an A rating.
- the results shown in the above table are merely illustrative since the results obtained when using other organolead salts of the type described herein ⁇ e.g., the corresponding diorganolead salts) are very similar. Similar results are also obtained when active ingredients are formulated with the conditioning agents of the type illustrated herein.
- a particular advantage of the present fungicides is my finding that in addition to being exceedingly potent agninstfungi they haveconsidcrable potency as insecticides. Moreover, as brought out above the presert fungicides are especially useful for agricultural applications since the vast majority of my fungicides are inherently relatively non-phytotoxic as regards various commercially important crops, especially at my recommended low use concentrations. Where it is desired to provide a general all-purpose agricultural fungicide it is preferable to employ my diand triaryllead salts since these appear to be even less phytotoxic than my alkyllead salts. On the other hand, my alkyllead salts are preferred for specific foliage-protectant fungicidal applications because of their generally greater fungicidal potency.
- My fungicides can be prepared by known methods. For example, to prepare my organolead chlorophenate fungicides the appropriate tetraorganolead compound (e.g., tetraethyllead, tetraamyllead, tetraphenyllead, etc.) is reacted with the desired chlorophenolic compound at a temperature in the range of about 75-175 C. in an inert organic solvent using a catalyst such as silica'gel.
- My organolead arenesulfonamides can be prepared by the procedure described by B. C. Saunders J. Chem. Soc., 1950, 684-7.
- My organolead thiosalicylate fungicides may be prepared by making use of the procedure described by H. Gilman and J. D. Robinson, Rec. trav. chim. 49, 766-8 (1930).
- To prepare my organolead acetate and organolead haloacetate fungicides recourse may be had to the procedures exemplified by A. K. Kochetkov and R. Kh. Freidlina, Uchenye Zapiski Moskov. Gosudarst. Univ. M. V. Lornonosova, No. 132, Org. Khim. No. 7, 144-50 (1950).
- Methods for preparing my organolead dihydrogen phosphate fungicides are typitied by the procedure described by Klippel, J. prakt.
- a fungicidal composition comprising as a principal active ingredient an organolead salt having the formula l I Ra Anion wherein R and R are selected from the group con sisting of alkyl groups containing up to about 8 carbon atoms and aryl groups containing from 6 to about 12 carbon atoms, wherein R is selected from the group consisting of alkyl groups containing up to about 8 carbon atoms, aryl groups containing from 6 to about 12 carbon atoms and Anion, and wherein Anion is a member of the group consisting of chlorophenate anions, arenesulfonamide' anions, thiosalicylate anion, acetate anion, haloacetate anions, dihydrogen phosphate anion, and arsanilate anion; and, as a carrier therefor, a substantially inert fungicidal adjuvant comprising a dispersant and surface active agent.
- composition of claim 1 further characterized in that said ingredient is a diaryllead salt as defined there- 3.
- composition of claim 1 further characterized in that said ingredient is a triaryllead salt as defined therein.
- composition of claim 1 further characterized in that said ingredient is a dialkyllead salt as defined .therein.
- composition of claim 1 further characterized in that said ingredient is a trialkyllead salt as defined therein.
- composition of claim 1 further characterized in that said ingredient is a dialkyllead diacetate.
- composition of claim 1 further characterized in that said ingredient is a trialkyllead acetate.
Description
lilo-18,33
,C3 .5: Citibllh xlmww 3,142,614 Patented July 28, 1964 3,142,614 -POLYVALENT ORGANO-LEAD FUNGIClDE Waldo B. Ligett, Pontiac, Mich., assignor to Ethyl Corporation, New York, N.Y., a corporation of Virginia No Drawing. Filed July 10, 1961, Ser. No. 122,660 14 Claims. (Cl. 167-42) This invention relates to when, and more particularly to new and poten cad-containing fungicidal compositions and their use in combatting fungi.
An object of this invention is to provide new fungicidal compositions. A further object is to provide new fungicidal compositions comprising conditioning agents and certain organolead salts as described herein. Still another object is, to provide new means and methods for combatting fungi.
The above and other objects are accomplished by the present invention whichin part resides in providing fungicidal compositions comprising a conditioning agent and, as a principal active fungicidal ingredient, a particular type of organolead salt containing 2 to 3 organo groups. The organolead salts in question have the formula Ri Ra Pb It: Anion whereinR, and R are alkyl or aryl groups, wherein R is alkyl, aryl or Anion. and wherein Anion is a member of the group consisting of chlorophenate anions, arenesulfonamide a nions, thiosal igl ate anion, a ge gge anion, haloaeetate z 1 n i qns, dihydrogen phgsphg te agion, and arsanilate ant on. R R and R are not necessarily the same. Preferably the alkyl groups each cort tairuip to about 8- carbon atoms. The aryl grb'fi'p's fi fef'e'i' a blf comm' a'bout 12 carbonmomrand arephenyl, alkyl-substituted phenyl, naphthyl and alkyl-substituted naphthyl groups. Generally, the dialkyllead and trialkyllead salts of the foregoing formula have greater potency against most common fungi than do the above diarylleadand triaryllead salts and for this reason these alkyllead salts can and preferably are used at lower concentrations in combatting or controlling fungi especially those that infest vegetation. it will be a simple matter in the light of this description to determine the optimum concentration of my fungicides for all intended uses and applications.
The chlorophenate anions of my novel fungicidal compositions can contain one, two. and pre erably, three, four or five chlorine atoms. The nucleus of the phenoxy group can be additionally substituted with loweralkyl wows-preferably methyl, ethyl. propyl or butyl groupswhen there are less than five chlorine substituents on the ring. Particularly effective are the diand triorganolead pentachlorophenates. Illustrative examples of the organolead chlorophenate salts used as fungicides pur- V suant to this invention include triethyllead chlorophenate (0-, m-, p-chloro isomers, or mixtures of these). triethyllead-2,4-dichlorophenate, the triethyllcad tetrachlorophenates, triethyllead pentaehlorophenate, diethyllead di- (2,5-dichlorophenate). dimethyllead di-t2.4,5-trichlorophenate). dibutyllead di-(p-chlorophenate), tri-Z-ethylhexylleact-2,4,6-trichlorophenate, diisopropyllead (ii-(2- methyl-6-chlpropheinate), diamyllead di-(pentachlorophenate), tri-2-octyllead-Z-chloro-4-tert-butylphenate, diphenyllead di-(2.4,S-trichlorophenatel, tri-p-tolyllead-oehlorophenate. tri-p-cumenyllead 2.5 dichloroplienate. naphthylethyllead di-( m-chlorophenatc), and the like. As pointed out above the pentachlorophenates are particularly preferred because of their very great elleetiveness as fungicides.
The arenesulfonamide anions of the present fungicides preferably contain from 6 to about it) carbon atoms in the arene group. Examples of these compounds are triethyllcad-p-tolucnc sulfonamidc, diethyllead di-(p-toluene sulfonamide), tripropyllead benzene sulfonamide, trihexyllead-p-cumene sulfonamide, dioctyllead di-(2,4-xylene sulfonamide), trixyllead-p-toluene sulfonamide (mixed xylyl isomers). diphcnyllead di-(benzene sulfonamide), and the like. The diand triorangolead arenesulfonamides are preferred for use in this invention because of their relatively low phytotoxicity against such common crops as cotton and soybeans.
Examples of my diand triorganolead thiosalicylate fungicides include triethyllead thiosalicylate, triheptyllead thiosalicylate, dimethyllead di-(thiosalicylate), methylphcriyllead di-(thiosalicylate), tri-m-tolyllead thiosalicylate. di-2 .5-xylyllead dHthiosalicylate), and the like.. A preferred feature of these compounds is their relatively, low phytotoxicity against such crops as cucumbers and soybeans.
lllustrative examples of my diand triorganolead acetate fungicides are triethyllead acetate trimethyllead acctate..diethyllead diace ae, l u ead diacetate, tributyllead acetate, triphenyllead acetate, diphenyllead diacetate, di-(2,5-diethylphenyl)lead diacctate, and the like. An advantageous and preferred characteristic of these diand triorganolead acetates is their relatively low phytotoxicity against such abundant crops as corn and wheat. Moreover. these compounds can be readily prepared at relatively low cost. and these factors, together with their considerable fungicidal potency render the acetates especially preferred for use in this invention.
The haloaeetate anions of my novel fungicidal compositions can contain 1, 2 or 3 halogen atoms in the acetate radical, these halogens being bromine. iodine, and preferably chlorine or fluorine. Mixtures of these halogen atoms can also be present. Specific examples of these fungicides include triethyllead trichloroacetate, triethyllead trifluoroacetate, diethyllead di-(monochloroacetate), dimethyllead di-(monochloroacetate). tributyllead dichloroacetate. trihexyllcad dichl'orolluoroacetate. triphenyllead trichloroacctatc. dicumenyllead di-(monofluoroacetate), phcnyldiethyllead tribromoacctate, diamyllead di- (monoiodoacetatc). and the like. These compounds are preferred for use in this invention because of their relatively low phytotoxicity against such plant species as soybeans.
Examples of my diand triorganolead dihydrogen phosphate fungicides include triethyllead dihydrogen phosphate. trioctyllead dihydrogen phosphate. tripheriyllead dihydrogen phosphate. diethyllead bis-(dihydrogen phosphate). di-o-tolyllead his-(dihydrogen phosphate), oetyldimethyllead dihydrogen phosphate. and the like.
Exemplary of my diand triorganolead arsanilate fudgicides are tricthyllcad arsanilate, tri-sec-butyl arsanilate. triphcnyllead arsanilate, triamyllead arsaniiate, dimethyllead diarsanilate. di-2.4-xylyllead diarsanilate. phenyl-ptolyllead diarsanilatc. and the like. An advantage of these compounds is their relatively low phytotoxicity as regards such crops as soybeans.
Another facet of this invention is my novel method of controlling and combatting fungi. Accordingly. one em bodiment of this invention is the method of combatting fungus which comprises contacting the fungus with a phytotoxic amount of a compound havingTitmformula given above. Another aspect of my invention is ihe provision of a method for controlling fungi which comprises treating matter susceptible to infestation by such organisms with a compound of the above formula.
The conditioning agents with which I admix my active fungicidal ingredients are of the type known to the art as substantially inert fungicidal adjuvants. These comprise a dispersant and a surface active agent. The purpose of these materials is to extend the active fungicidal ingredient to insure its efficacious penetration into or application onto the locus being treated and to adapt the active fungicidal ingredients for ready and efficient application to pests and to the loci of the fungi using conventional equipment. In general such formulations comprise both the liquid and solid types as well as the Aerosol" type of formulation. The liquid type of formulation can have water, an organic solvent, an oil-' water emulsion and the like as the conditioning agent. The liquid ingredient of the formulation may further contain a surface active agent such as a detergent, a soap or other wetting agent' It is also intended that the term conditioning agent" include solid carriers such as talc. pyrophyllite, Attaclay, kieselguhr, chalk, diatomaceous earth, and the like; and various mineral powders such as calcium carbonate and the like which act as a dispersant, as a carrier, and in some instances perform the function of a surface active agent. Among the preferred formulations employing solid conditioning agents are those known as wettable powders. In general these wettable powders include the active ingredient, a surface active agent and an inert carrier such as soybean flour, sulfur, calcium oxide, mica, talc, humus and the like. In preparing such concentrated wettable powders it is preferred to employ between about 0.1 and 5 percent of the surface active agent based upon the amount of active fungicidal ingredient used and up to about 85 percent of the inert solid carrier based upon the total amount of the formulation. Such formulations provide the advantage of permitting storage and transportation of the pesticides in readily handled form and permit further dilution by simple admixture with water to provide finished liquid formulations at the time of application.
Thus the formulations which comprise my active ingredient in combination with a conditioning agent provide liquid. solid and aerosol formulations in a.,form
adapted to be readily applied to thematerial to be t. called. The liquid compositions, either solutions or dispe'sions, frequently contain a surface active dispersing agent in amount sufficient to render the composition readily dispersable in water for aqueous spray application. The solid formulations also frequently contain a surface active dispersing agent in amount sufficient to impart water dispersibility to the compositions. When dust application is desired a surface active dispersing agent can be omitted. In this case the formulation will still contain a solid carrier, extender or diluent as conditioning agent.
The surface active dispersing agents referred to herein are sometimes known as wetting, dispersing or penetrating agents. They are agents which cause the formulations to be easily dispersed in water. They can be of the anionic, cationic or non-ionic type and include salts of long chain fatty. acids, sulfonated oilsboth vegetable ..nd animalpetroleum oils, sulfates of long chain alco- 'hols, phosphates of long chain alcohols, various polyethylene oxides and condensation products of ethylene oxide with alcohols and phenols, quaternary ammonium salts and the like. The surface active agent will usually be present to the extent of 0.1 to 5 percent of the formulation.
The active ingredients can also be dispersed or suspended in various organic solvents such as alcohols. ketones, hydrocarbons, petroleum cuts such as kerosene, dimethylformamide and the like. In this case a surface active dispersing agent is usually present to provide ready dispersibility with water.
To illustrate certain of the formulations employed, I mix 50 parts of tributyllead acetate with 50 parts of diatomaceous earth and 3 parts of sodium lauryl sulfate and then grind the mixture to obtain a wettable powder formulation suitable for dilution with water. I also mix 30 parts of diisopropyllead di-(pentachlorophenate) with 500 parts of fuller's earth to obtain a dust formulation suitable for application.
To obtain a liquid concentration mix parts of triphenyllead p-tcrt-butylbenzene sulfonamide-with 50 parts of kerosene and 2 parts of cetyldimethylhenzylammonium chloride as a wetting agent. To make oil-water emulsion from this formulationl add it with vigorous stirring to 400 parts of water.
Other formulations comprising active ingredients of this invention together with conditioning agents are prepared by similar means and ha e in general make-ups similar to those given above.
in general all my finished formulations, depending upon the application in mind, usually contain between about 0.1 to 10.000 p.p.m. of active ingredient. A preferred range for agricultural application is between 0.1 and 2.000 p.p.m. In other applications such as in wood treating, plastics, paper and textiles the amount of active ingredient may be higher than 2,000 ppm.
The fungicidal effectiveness of my compounds can be demonstrated by the following test.
Slide germination lcsL-By the slide germination test the concentration of the chemical required to inhibit germination of spores from 7- to 10-day old cultures of Allernrm'a oleracca and Sclerotinia fructicola is determined. Concentrations of active ingredients used in this test are 1000, 100, 10, and 1.0 ppm. The specified concentrations of active ingredient are prepared in aqueous suspension by a series of test tube dilutions. Fol lowing the initial dilutions, four volumes of suspension are diluted with one volume of spore stimultant and spore suspension. The spore stimulant is added to insure a high and relatively stable percentage of germination in the checks. Drops of the test suspension mixture, and an untreated control are pipetted onto glass slides. The glass slides are placed in moist chambers for 20 hours incubation at 22 C. Germination counts are made by counting potentially viable spores, those spores that would germinate under the normal conditions of the control. The percent germination is expressed by the following equation: observed percent germination l00+percent germination in the control. Test compounds are given letter ratings which correspond to the concentration that inhibits germination of half of the spores (ED :AA=0.l to 1.0 p.p.m.; A=1.0 to 10 ppm; 8:10 to 100 ppm: (3: 100 to 1000 p.p.m.; and D= l000 ppm. The glass slide germination test by the test tube dilution method is adapted from a procedure recommended by the American Phytopathological Societys committee on standardization of fungicidal tests. (Phytopathology 37, 354-356 (1947).)
In such a test typical fungicides of my invention gave the following results:
Slide Germination Organolr-ad Salt.
In the above table a minus sign indicates the average results of two tests where the determinations varied by one rank. For example, a rating of AA shows that in one determination the compound had an AA rating while in another it had an A rating. The results shown in the above table are merely illustrative since the results obtained when using other organolead salts of the type described herein {e.g., the corresponding diorganolead salts) are very similar. Similar results are also obtained when active ingredients are formulated with the conditioning agents of the type illustrated herein.
A particular advantage of the present fungicides is my finding that in addition to being exceedingly potent agninstfungi they haveconsidcrable potency as insecticides. Moreover, as brought out above the presert fungicides are especially useful for agricultural applications since the vast majority of my fungicides are inherently relatively non-phytotoxic as regards various commercially important crops, especially at my recommended low use concentrations. Where it is desired to provide a general all-purpose agricultural fungicide it is preferable to employ my diand triaryllead salts since these appear to be even less phytotoxic than my alkyllead salts. On the other hand, my alkyllead salts are preferred for specific foliage-protectant fungicidal applications because of their generally greater fungicidal potency.
My fungicides can be prepared by known methods. For example, to prepare my organolead chlorophenate fungicides the appropriate tetraorganolead compound (e.g., tetraethyllead, tetraamyllead, tetraphenyllead, etc.) is reacted with the desired chlorophenolic compound at a temperature in the range of about 75-175 C. in an inert organic solvent using a catalyst such as silica'gel. My organolead arenesulfonamides can be prepared by the procedure described by B. C. Saunders J. Chem. Soc., 1950, 684-7. My organolead thiosalicylate fungicides may be prepared by making use of the procedure described by H. Gilman and J. D. Robinson, Rec. trav. chim. 49, 766-8 (1930). To prepare my organolead acetate and organolead haloacetate fungicides recourse may be had to the procedures exemplified by A. K. Kochetkov and R. Kh. Freidlina, Uchenye Zapiski Moskov. Gosudarst. Univ. M. V. Lornonosova, No. 132, Org. Khim. No. 7, 144-50 (1950). Methods for preparing my organolead dihydrogen phosphate fungicides are typitied by the procedure described by Klippel, J. prakt.
Chem. [1] 81, 286 (1860.) To form my organolead arsanilate fungicides generally similar procedures are used, e.g., condensation of the appropriate organoiead hydroxide with arsanilic acid.
Iclaim:
1. A fungicidal composition comprising as a principal active ingredient an organolead salt having the formula l I Ra Anion wherein R and R are selected from the group con sisting of alkyl groups containing up to about 8 carbon atoms and aryl groups containing from 6 to about 12 carbon atoms, wherein R is selected from the group consisting of alkyl groups containing up to about 8 carbon atoms, aryl groups containing from 6 to about 12 carbon atoms and Anion, and wherein Anion is a member of the group consisting of chlorophenate anions, arenesulfonamide' anions, thiosalicylate anion, acetate anion, haloacetate anions, dihydrogen phosphate anion, and arsanilate anion; and, as a carrier therefor, a substantially inert fungicidal adjuvant comprising a dispersant and surface active agent.
2. The composition of claim 1 further characterized in that said ingredient is a diaryllead salt as defined there- 3. The composition of claim 1 further characterized in that said ingredient is a triaryllead salt as defined therein.
4. The composition of claim 1 further characterized in that said ingredient is a dialkyllead salt as defined .therein.
5. The composition of claim 1 further characterized in that said ingredient is a trialkyllead salt as defined therein.
6. The composition of claim 1 further characterized in that said ingredient is a dialkyllead diacetate.
7. The composition of claim 1 further characterized in that said ingredient is a trialkyllead acetate.
8. The method of combatting fungus which comprises contacting the fungus with a phytotoxic amount of an organolead salt as defined in claim 1.
9. The method of claim 8 further characterized in that said salt is a diaryllead salt.
10. The method of claim 8 further characterized in that said salt is a triaryllead salt.
11. The method of claim 8 further characterized in that said salt is a dialkyllead salt.
12. The method of claim 8 further characterized in that said salt is a trialkyllead salt. a
13. The method of claim 8 further characterized in that said salt is a dialkyllead diacetate.
14. The method of claim 8 further characterized in that said salt is a trialkyllead acetate.
References Cited in the file of this patent UNITED STATES PATENTS 2,640,006 Ligett et al May 26, 1953 OTHER REFERENCES Hannas Handbook of Agricultural Chemicals, 2nd Edition, 1958, pp. 157-8.
Claims (1)
1. A FUNGICIDAL COMPOSITION COMPRISING AS A PRINCIPAL ACTIVE INGREDIENT AN ORGANOLEAD SALT HAVING THE FORMULA
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3322779A (en) * | 1963-04-01 | 1967-05-30 | Int Lead Zinc Res | Di- and triphenyllead sulfides having substituent radicals joined to the sulfur atom |
US3420700A (en) * | 1966-04-29 | 1969-01-07 | Us Agriculture | Process for imparting rot-resistance to an organic textile material and the resulting material |
US3522352A (en) * | 1963-04-01 | 1970-07-28 | Int Lead Zinc Res | Method of inhibiting fungal growth with lead mercaptides |
US3683090A (en) * | 1970-06-15 | 1972-08-08 | Malcolm C Henry | Methods of repelling rodents using tetravalent organo-lead compounds |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2640006A (en) * | 1950-10-28 | 1953-05-26 | Ethyl Corp | Nu-organolead-phthalimides as fungicides |
-
1961
- 1961-07-10 US US122660A patent/US3142614A/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2640006A (en) * | 1950-10-28 | 1953-05-26 | Ethyl Corp | Nu-organolead-phthalimides as fungicides |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3322779A (en) * | 1963-04-01 | 1967-05-30 | Int Lead Zinc Res | Di- and triphenyllead sulfides having substituent radicals joined to the sulfur atom |
US3522352A (en) * | 1963-04-01 | 1970-07-28 | Int Lead Zinc Res | Method of inhibiting fungal growth with lead mercaptides |
US3420700A (en) * | 1966-04-29 | 1969-01-07 | Us Agriculture | Process for imparting rot-resistance to an organic textile material and the resulting material |
US3420701A (en) * | 1966-04-29 | 1969-01-07 | Us Agriculture | Process for imparting rot-resistance to an organic textile material and the resulting material |
US3683090A (en) * | 1970-06-15 | 1972-08-08 | Malcolm C Henry | Methods of repelling rodents using tetravalent organo-lead compounds |
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