BRPI0804557A2 - dimethylmercaptopyrimidylethane derived organostannic compound for fungicide formulation - Google Patents
dimethylmercaptopyrimidylethane derived organostannic compound for fungicide formulation Download PDFInfo
- Publication number
- BRPI0804557A2 BRPI0804557A2 BRPI0804557-7A BRPI0804557A BRPI0804557A2 BR PI0804557 A2 BRPI0804557 A2 BR PI0804557A2 BR PI0804557 A BRPI0804557 A BR PI0804557A BR PI0804557 A2 BRPI0804557 A2 BR PI0804557A2
- Authority
- BR
- Brazil
- Prior art keywords
- dimethyl
- compound
- tin
- ethane
- atom
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 84
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 238000009472 formulation Methods 0.000 title claims abstract description 19
- 230000000855 fungicidal effect Effects 0.000 title abstract description 42
- 239000000417 fungicide Substances 0.000 title abstract description 17
- SHEKAOKUJSEHCS-UHFFFAOYSA-N CC(C1=NC=CC=N1)[S+](C)C Chemical compound CC(C1=NC=CC=N1)[S+](C)C SHEKAOKUJSEHCS-UHFFFAOYSA-N 0.000 title 1
- -1 4,6-dimethyl- 2-pyrimidyl Chemical group 0.000 claims abstract description 20
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 claims abstract description 14
- VNIBQEHRIFPZMT-UHFFFAOYSA-N CC1=NC(=NC(=C1C(C)C=1C(=NC(=NC1C)S)C)C)S Chemical compound CC1=NC(=NC(=C1C(C)C=1C(=NC(=NC1C)S)C)C)S VNIBQEHRIFPZMT-UHFFFAOYSA-N 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 239000011593 sulfur Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 20
- 229910052718 tin Inorganic materials 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- BDGYNZZXJSZSNN-UHFFFAOYSA-N 2-[1-(4,6-dimethylpyrimidin-2-yl)sulfanylethylsulfanyl]-4,6-dimethylpyrimidine Chemical compound CC1=NC(=NC(=C1)C)SC(C)SC1=NC(=CC(=N1)C)C BDGYNZZXJSZSNN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical compound [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 1
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- 239000004480 active ingredient Substances 0.000 abstract description 29
- 238000000034 method Methods 0.000 abstract description 13
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- ZTONKKHCXJTROW-UHFFFAOYSA-N n-(2-oxopropyl)benzamide Chemical compound CC(=O)CNC(=O)C1=CC=CC=C1 ZTONKKHCXJTROW-UHFFFAOYSA-N 0.000 description 4
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- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000001424 substituent group Chemical group 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- RAFAYWADRVMWFA-UHFFFAOYSA-N 4,6-dimethyl-1h-pyrimidine-2-thione Chemical compound CC1=CC(C)=NC(S)=N1 RAFAYWADRVMWFA-UHFFFAOYSA-N 0.000 description 2
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- WNBGYVXHFTYOBY-UHFFFAOYSA-N benzyl-dimethyl-tetradecylazanium Chemical compound CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 WNBGYVXHFTYOBY-UHFFFAOYSA-N 0.000 description 2
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- 239000000575 pesticide Substances 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical class C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- 125000005402 stannate group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- RNVJQUPAEIQUTC-UHFFFAOYSA-N tricyclohexyltin Chemical compound C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 RNVJQUPAEIQUTC-UHFFFAOYSA-N 0.000 description 1
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 description 1
- NFHRNKANAAGQOH-UHFFFAOYSA-N triphenylstannane Chemical compound C1=CC=CC=C1[SnH](C=1C=CC=CC=1)C1=CC=CC=C1 NFHRNKANAAGQOH-UHFFFAOYSA-N 0.000 description 1
- NSPWVJAKNXJHEP-UHFFFAOYSA-N tripropyltin Chemical compound CCC[Sn](CCC)CCC NSPWVJAKNXJHEP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
- A01N55/04—Tin
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Trata de composto organoestânico derivado da reação entre cloreto de trifenilestanho(IV) e bis-(4,6-dimetil-2-mercaptopirimidil)-etano de fórmula geral [SnxClxPh3x(R1R2CH2CH2R2R1) (1) {R1 = 4,6-dimetil-2-pirimidil, R2 = S (enxofre), x = 1, 2, 3 ,4} com propriedade fungicida, utilizável como princípio ativo único na formulação de novo fungicida ou como ingrediente nas formulações fungicidas existentes para o controle de doenças das plantas e de fungos em ambiente. Vários organoestânicos são conhecidos e empregados como ingredientes em composição fungicida. Entretanto, problemas como a resistência dos fungos, baixo valor do MIC (Concentração Minima Inibitória) e altas concentrações do ingrediente ativo dificultam o controle de doenças. A presente invenção tem por objetivo o desenvolvimento de composto fungicida para o controle de doenças de plantas e outros fungos toxicogênicos e alergênicos. A preparação do organoestânico envolve técnica de processo de síntese no estado sólido bem como em solução. O resultado do teste fungitóxico e crescimento micelial mostram claramente a atividade da presente invenção contra todos os fungos testados.It is an organotin compound derived from the reaction between triphenyltin (IV) chloride and bis- (4,6-dimethyl-2-mercaptopyrimidyl) -ethane of the formula [SnxClxPh3x (R1R2CH2CH2R2R1) (1) {R1 = 4,6-dimethyl- 2-pyrimidyl, R2 = S (sulfur), x = 1, 2, 3, 4} with fungicidal property, usable as a single active ingredient in the formulation of new fungicide or as an ingredient in existing fungicidal formulations for plant disease control and of fungi in environment. Various organotins are known and employed as ingredients in fungicidal composition. However, problems such as fungal resistance, low MIC (Minimal Inhibitory Concentration) value, and high active ingredient concentrations make disease control difficult. The present invention aims at the development of fungicidal compound for the control of plant diseases and other toxicogenic and allergenic fungi. The preparation of organotin involves solid state synthesis technique as well as solution. The results of the fungitoxic test and mycelial growth clearly show the activity of the present invention against all tested fungi.
Description
"COMPOSTO ORGANOESTÂNICO DERIVADO DEDIMETILMERCAPTOPIRIMIDILETANO PARA FORMULAÇÃO DE FUNGICIDA""DIMETHYLMERCAPTOPYRIMIDILETAN ORGANESTATIC COMPOUND FOR FUNGICIDE FORMULATION"
A presente invenção refere-se à preparação e efeito fungicida de compostode coordenação ou organoestânico derivado da reação entre o cloreto detrifenilestanho(IV) com o bis-(4,6-dimetil-2-mercaptopirimidil)-etano contra fungosfitopatogênicos, toxicogênicos, alergênicos e outros. O composto organoestânicoderivado, objeto do presente pedido de patente, tem fórmula geral[SnxClxPh3x(R1R2CH2CH2R2R1)] {R1 = 4,6-dimetil-2-pirimidil, R2 = S (enxofre), x =1,2, 3, 4}. O nome do organoestânico varia de acordo com o número de gruposclorotrifenilestanho em sua fórmula. Para x =1 não se utiliza prefixo, mas para x =2 usa-se o prefixo bis, para x = 3 usa-se o prefixo tris e, para x =4 usa-se oprefixo tetraquis. Para x = 2 o nome será bis-(4,6-dimetil-2-mercaptopirimidil)-etano-7,7'-bis-(clorotrifenilestanho(IV)) ou bis-(4,6-dimetil-2-mercaptopirimidil)-etano-3,3'-bis-(clorotrifenilestanho(IV)) ou bis-(4,6-dimetil-2-mercaptopirimidil)-etano-7,3'-bis-(clorotrifenilestanho(IV)) ou bis-(4,6-dimetil-2-mercaptopirimidil)-etano-3,7'-bis-(clorotrifenilestanho(IV)) ou bis-(4,6-dimetil-2-pirimidiltio)-etano-7,7'-bis-(clorotrifenilestanho(IV)) ou bis-(4,6-dimetil-2-pirimidil-tio)-etano-3,3'-bis-(clorotrifenilestanho(IV)) ou bis-(4,6-dimetil-2-pirimidiltio)-etano-7,3'-bis-(clorotrifenilestanho(IV)) ou bis-(4,6-dimetil-2-pirimidiltio)-etano-3,7'-bis-(clorotrifenilestanho(IV)). A presente invenção refere-se ao setor técnico defitossanidade da área de Agronomia e síntese de compostos de coordenação daárea de Química.The present invention relates to the preparation and fungicidal effect of coordination or organotin compound derived from the reaction between detriphenyl tin (IV) chloride and bis- (4,6-dimethyl-2-mercaptopyrimidyl) -ethane against fungi, pathogens, toxicogens, allergens and others. The derivatized organostannic compound object of the present patent application has the general formula [SnxClxPh3x (R1R2CH2CH2R2R1)] {R1 = 4,6-dimethyl-2-pyrimidyl, R2 = S (sulfur), x = 1,2,3,4} . The name of the organotin varies according to the number of chlorotriphenyl tin groups in its formula. For x = 1 no prefix is used, but for x = 2 we use the prefix bis, for x = 3 we use the prefix tris and for x = 4 we use the prefix tetrakis. For x = 2 the name will be bis- (4,6-dimethyl-2-mercaptopyrimidyl) ethane-7,7'-bis- (chlorotriphenyl tin (IV)) or bis (4,6-dimethyl-2-mercaptopyrimidyl) -ethane-3,3'-bis- (chlorotriphenyltin (IV)) or bis- (4,6-dimethyl-2-mercaptopyrimidyl) -ethane-7,3'-bis- (chlorotriphenyltin (IV)) or bis- ( 4,6-dimethyl-2-mercaptopyrimidyl) ethane-3,7'-bis- (chlorotriphenyltin (IV)) or bis (4,6-dimethyl-2-pyrimidylthio) -ethane-7,7'-bis- (chlorotriphenyl tin (IV)) or bis (4,6-dimethyl-2-pyrimidylthio) ethane-3,3'-bis- (chlorotriphenyl tin) or bis (4,6-dimethyl-2-yl) pyrimidylthio) -ethane-7,3'-bis (chlorotriphenyl tin (IV)) or bis (4,6-dimethyl-2-pyrimidylthio) ethane-3,7'-bis (chlorotriphenyl tin (IV)). The present invention relates to the technical sector of agronomy and synthesis of compounds coordinating the chemistry area.
Estado da técnicaState of the art
Existem patentes que utilizam o precursor metálico cloreto detrifenilestanho(IV), ou outro precursor de estanho na preparação de materiaiscom propriedade fungicida, bactericida, algicida, entre outras.There are patents that use the metal precursor detriphenyl tin (IV), or other tin precursor in the preparation of materials with fungicidal, bactericidal, algicidal properties, among others.
A patente USPTO 4158001 relata o uso de triorganoestânicos (SnCIR3, R= butil, fenil, propil) na preparação de derivados de óxidos de hidroxidiazenio e N-ciclohexilhidroxidiazenio, os quais apresentam um bom efeito fungicida para apreservação da madeira ou no uso como preservativo de emulsão de tintas,couro, adesivo e papel. A desvantagem desta invenção refere-se à altaconcentração do ingrediente ativo. O presente pedido de patente se diferenciadesta patente no que se refere à aplicação industrial do princípio ativo bem comona natureza química do precursor orgânico, a mercaptopirimidina.USPTO 4158001 discloses the use of triorgananes (SnCIR3, R = butyl, phenyl, propyl) in the preparation of hydroxydiazene oxide and N-cyclohexylhydroxydiazene oxide derivatives, which have a good fungicidal effect on wood preservation or as a preservative of wood. paint, leather, adhesive and paper emulsion. The disadvantage of this invention relates to the high concentration of the active ingredient. The present patent application differs from this patent with respect to the industrial application of the active principle as well as the chemical nature of the organic precursor, mercaptopyrimidine.
As patentes USPTO 3931262 e USPTO 3933877 relatam a obtenção detriorganoestânicos derivados de sais de ácido mercaptocarboxílico, ácido 2-mercaptopropiônico, ácido mercaptoalcanosulfônico, entre outros, com atividadebiocida, bem como apresentando propriedade hidrofílica. Nestas patentes, estapropriedade abaixa o caráter volátil do material, o que viabiliza o seu usocomercial. Entretanto, isto reduz a aplicação desta invenção como princípio ativoúnico em misturas sólidas (pó). Ainda nestas patentes, o caráter hidrofílico sedeve a uma ligação química do radical triorganoestânico ao enxofre domercaptano. O material, nestas patentes, apresenta baixa toxicidade podendo seraplicado na proteção de plantas contra os fungos fitopatogênicos. A desvantagemdestas invenções refere-se à alta concentração do ingrediente ativo e o caráterfitotóxico do princípio ativo.USPTO 3931262 and USPTO 3933877 report the obtaining of detriorgano-stannic salts derived from mercaptocarboxylic acid, 2-mercaptopropionic acid, mercaptoalcanosulfonic acid, among others, with biocidal activity, as well as having hydrophilic properties. In these patents, this property lowers the volatile character of the material, which makes its use possible. However, this reduces the application of this invention as a single active ingredient in solid mixtures (powder). Also in these patents, the hydrophilic character predisposes to a chemical bond of the triorganostannic radical to domercaptan sulfur. The material in these patents has low toxicity and can be applied in the protection of plants against phytopathogenic fungi. The disadvantage of these inventions relates to the high concentration of the active ingredient and the phytotoxic character of the active ingredient.
A patente USPTO 6270810 relata uma composição fungieida para uso nocontrole de fungos fitopatogênicos de plantas. O principal princípio ativo dacomposição fungieida é o composto N-[3X1'-cloro-3'-metil-2'-oxopentil)]-3,5-dicloro-4-metilbenzamida ou N-[3X1'-cloro-3'-metil-2'-oxopentil)]-3,5-dibromo-4-ciano-benzamida ou uma mistura de ambos. O composto apresentado na patenteUSPTO 6270810 consiste de, além destes, da adição de outros fungicidasorganoestânicos como o hidróxido de fentina (hidróxido de trifenilestanho) eacetato de fentina (acetato de trifenilestanho), fungicidas contendo sais decobre(l) e cobre(ll), bem como fungicidas orgânicos como componentes. Nestapatente, fica evidente que para a melhoria da eficácia do composto, é necessáriaadição de compostos já existentes. Esta invenção apresenta a desvantagem deconter um ingrediente fitotóxico em sua formulação, bem como o fato daaplicação do princípio ativo em campo estabelecer alta concentração.USPTO 6270810 discloses a fungiidal composition for use in the control of plant phytopathogenic fungi. The main active ingredient of fungiide composition is the compound N- [3X1'-chloro-3'-methyl-2'-oxopentyl)] - 3,5-dichloro-4-methylbenzamide or N- [3X1'-chloro-3'- methyl-2'-oxopentyl)] - 3,5-dibromo-4-cyano-benzamide or a mixture of both. The compound disclosed in USPTO 6270810 consists of, in addition to these, the addition of other organotinic fungicides such as fentin hydroxide (triphenyltin hydroxide), fentin acetate (triphenyltin acetate), copper (1) and copper (11) salts as well as fungicides. as organic fungicides as components. In this patent, it is evident that for the improvement of compound efficacy, addition of existing compounds is required. This invention has the disadvantage of having a phytotoxic ingredient in its formulation, as well as the fact that the application of the active ingredient in the field establishes high concentration.
A patente USPTO 4115094 relata o efeito herbicida e pesticida deorganoestânicos tetravalentes contendo três ligações estanho-carbono oriundosde grupos butil, fenil, bem como de derivados de sacarose. A invenção pode serutilizada também no combate ao crescimento de plantas aquáticas, fixador detintas. Alguns organoestânicos derivados da sacarose apresentam certo efeitofungicida, algicida, herbicida e bactericida. São compostos estáveis podendo seraplicados em spray, pó, ou em formulações líquidas porque quando expostos àluz do sol ou adicionados ao solo, os compostos se decompõem a um compostoinorgânico estável, não produzindo poluição ambiental por longa exposição e,além disso, apresentam atividade biológica na concentração de 1 ppmanalogamente a outros biocidas organoestânicos como o oxido detributilestanho(IV). Entretanto, esta invenção apresenta a desvantagem de conterum ingrediente fitotóxico em sua formulação, bem como o fato da aplicação doprincípio ativo em campo estabelecer uma alta concentração.USPTO 4115094 discloses the tetravalent herbicidal and pesticidal effect of tetravalent organotin containing three tin-carbon bonds derived from butyl, phenyl as well as sucrose derivatives. The invention may also be used in combating the growth of aquatic plants, fixative detectors. Some sucrose-derived organotins have a certain fungicidal, algicidal, herbicidal and bactericidal effect. They are stable compounds that can be applied in spray, powder, or liquid formulations because when exposed to sunlight or added to the soil, the compounds decompose to a stable inorganic compound, producing no long exposure environmental pollution and, in addition, have biological activity in the environment. concentration of 1 ppmanally to other organotin biocides such as detributyl tin oxide (IV). However, this invention has the disadvantage of containing a phytotoxic ingredient in its formulation, as well as the fact that the application of the active ingredient in the field establishes a high concentration.
A patente USPTO 4578489 relata novos compostos organoestânicos deamônio com alta atividade biocida, onde os compostos ativos contêm radicaistributil, trifenil ligados ao centro metálico. O composto ativo preferido dimetil-benzil-n-tetradecilamônio tri-n-butildicloroestanato(IV) ou dimetil-benzil-n-tetradecilamônio tri-n-butildifluoroestanato(IV) tem o centro metálicopentacoordenado. Estes, entre outros compostos descritos nesta patente, sãosolúveis em água, apresentando um amplo espectro de ação como fungicidas,acaricidas, herbicidas e algicidas, além de terem uma aplicação industrial naproteção de madeira, papel, couro, tintas de maneira geral, borracha, etc. Adesvantagem desta invenção refere-se à alta concentração do ingrediente ativo ealto valor do MIC (Concentração Mínima Inibitória).USPTO 4578489 discloses new organotin deamonium compounds with high biocidal activity, where the active compounds contain radicaistributyl, triphenyl attached to the metal center. The preferred active compound dimethylbenzyl-n-tetradecylammonium tri-n-butyldichloroestanate (IV) or dimethyl benzyl-n-tetradecylammonium tri-n-butyldifluorostannate (IV) has the pententordinate metal center. These, among other compounds described in this patent, are water soluble, having a broad spectrum of action as fungicides, acaricides, herbicides and algaecides, and have an industrial application in the protection of wood, paper, leather, paint, rubber, etc. . The advantage of this invention relates to the high concentration of the active ingredient and the high value of the MIC (Minimum Inhibitory Concentration).
A patente USPTO 5436267 relata o uso de N-fenilcarbamato ou seu salcomo ingrediente ativo em composição biocida para o controle de pragas naagricultura. O carbamato ativo pode ter vários substituintes como grupos alquiltioou alquilsulfonil, além de outros como benzimidazol, benzotiazolil, benzimidazolil,imidazopiridil, dihidrobenzofuril, tiazolil, pirimidil, pirazinil, benzotiazinil, entreoutros. O material decorrente desta invenção pode ser usado em combinaçãocom outros fungicidas comercializados, como o hidróxido de trifenilestanho e oacetato de trifenilestanho. O carbamato, o material orgânico objeto destainvenção, e seus derivados podem ser utilizados como ingredientes ativos naagricultura e horticultura contra doenças de plantas. A desvantagem destainvenção refere-se à alta concentração do ingrediente ativo, além de apresentarpropriedade fitotóxica.A patente USPTO 4678804 relata o efeito fungicida e inseticida debenziltioestananos. Os compostos contêm radicais tais como tributil, tricyclohexile trifenil ligados ao átomo de estanho(IV). Por exemplo, os compostos R'benziltio-trifenilestanano onde R' = 2,5-dimetil-, 2,6-diclorobenziltio-, 4-etil-, 2-trifluorometil-,3-trifluorometil-, 4-trifluorometil-, 3-nitro-, 3,5-dinitro-, 2-cloro-, 2,4,6-tricloro-, 2-bromo-, 4-bromo-, 2-fluoro-, 4-fluoro-, 4-ter-butil-, 2-metil-, 2,4,6-trimetil-. Ainvenção desta patente está voltada para o seu potencial fungicida na proteçãode plantas contra uma variedade de fungos. A desvantagem desta invençãorefere-se ao fato do princípio ativo não ter um amplo espectro de ação comotambém a alta concentração do ingrediente ativo na composição do fungicida.USPTO 5,436,267 reports the use of N-phenylcarbamate or its salt as an active ingredient in biocidal composition for pest control in agriculture. Active carbamate may have various substituents such as alkylthio or alkylsulfonyl groups, but others such as benzimidazole, benzothiazolyl, benzimidazolyl, imidazopyridyl, dihydrobenzofuryl, thiazolyl, pyrimidyl, pyrazinyl, benzothiazinyl, among others. The material derived from this invention may be used in combination with other commercially available fungicides such as triphenyltin hydroxide and triphenyltin acetate. Carbamate, the non-inventive organic material, and its derivatives can be used as active ingredients in agriculture and horticulture against plant diseases. The disadvantage of this invention is the high concentration of the active ingredient in addition to its phytotoxic property. USPTO 4678804 reports the fungicidal and insecticidal effect of benzylthiostannans. The compounds contain radicals such as tributyl, tricyclohexile triphenyl attached to the tin (IV) atom. For example, the compounds R'benzylthio triphenylstannane where R '= 2,5-dimethyl-, 2,6-dichlorobenzylthio-, 4-ethyl-, 2-trifluoromethyl-, 3-trifluoromethyl-, 4-trifluoromethyl-, 3- nitro-, 3,5-dinitro-, 2-chloro-, 2,4,6-trichloro-, 2-bromo-, 4-bromo-, 2-fluoro-, 4-fluoro-, 4-tert-butyl- 2,2-methyl-, 2,4,6-trimethyl-. The invention is concerned with its fungicidal potential in protecting plants against a variety of fungi. The disadvantage of this invention relates to the fact that the active principle does not have a broad spectrum of action as well as the high concentration of the active ingredient in the composition of the fungicide.
A patente USPTO 4654368 relata a atividade de triorganoestânicosderivados de silatrane em composições pesticidas, fungicidas, inseticidas, bemcomo agente protetor contra organismos marinhos. Os compostos ativos contêmenxofre, organometálicos de silício e organoestânicos. Estes últimos sãoderivados de vários precursores como o cloreto ou brometo detrimetilestanho(IV), de trietilestanho(IV), de tri-n-propilestanho(IV), de tri-n-butilestanho(IV), de trioctilestanho(IV), de triciclohexilestanho(IV) etrifenilestanho(IV). A desvantagem desta invenção refere-se ao uso deingrediente ativo fitotóxico, o que reduz a aplicação deste material como um bomfungicida.USPTO 4654368 reports the activity of silatran-derived triorganostannins in pesticidal, fungicidal, insecticidal compositions as well as a protective agent against marine organisms. The active compounds contain sulfur, silicon organometallic and organotin. The latter are derived from various precursors such as trimethyl tin (IV), triethyl tin (IV), tri-n-propyl tin (IV), tri-n-butyl tin (IV), tricycline (IV), tricyclohexyl tin chloride or bromide. (IV) ethenyl tin (IV). The disadvantage of this invention relates to the use of phytotoxic active ingredient, which reduces the application of this material as a good fungicide.
A patente USPTO 4581373 relata sobre derivados organoestânicosbiologicamente ativos em concentrados emulsificantes, bem como métodos parao controle de infestações em plantas. Os compostos orgânicos associados aoorganoestânico são ácidos lipofílicos cujos sais derivados contêm enxofre oufósforo em sua composição química. Entre os radicais organoestânicosencontram-se o trifenilestanho(IV) e o triciclohexilestanho(IV). Os ácidos contêmtambém cadeia carbônica de 6 a 18 átomos de carbono. O composto ativo édecorrente da mistura de outros fungicidas como o hidróxido detriciclohexilestanho(IV) ou o hidróxido de trifenilestanho(IV) com os ácidoslipofílicos. A concentração do princípio ativo no concentrado emulsificantedepende do solvente utilizado, mas, de uma maneira geral, o material é utilizadoem quantidade suficiente em solução aquosa diluída. A desvantagem destainvenção refere-se à alta concentração do ingrediente ativo, além de apresentarpropriedade fitotóxica.USPTO 4581373 discloses biologically active organostannic derivatives in emulsifying concentrates as well as methods for controlling plant infestations. Organic compounds associated with organotin are lipophilic acids whose derived salts contain sulfur or phosphorus in their chemical composition. Among the organotin radicals are triphenyl tin (IV) and tricyclohexyl tin (IV). Acids also contain carbon chains of 6 to 18 carbon atoms. The active compound is due to the mixture of other fungicides such as dicyclohexyl tin (IV) hydroxide or triphenyl tin (IV) hydroxide with lipophilic acids. The concentration of the active ingredient in the emulsifiable concentrate depends on the solvent used, but generally the material is used in sufficient amount in dilute aqueous solution. The disadvantage of this invention refers to the high concentration of the active ingredient, besides presenting phytotoxic property.
A patente USPTO 4514225 relata a preparação e uso de um compostotriorganoestânico derivado de acetilsalicilatos para ò controle de microorganismostais como bactéria, algas, organismos marinhos, bem como na preservação demadeira. Precursores metálicos de fórmula geral SnCIR3 (R = butil, fenil, alquil eciclohexil) foram utilizados no preparo dos compostos ativos. Os compostospodem ser aplicados em solução, emulsão, dispersões em água ou através desolventes orgânicos. Os compostos descritos nesta patente podem ser aplicadosem combinação com outros compostos com atividade biocida. A desvantagemdesta invenção refere-se à alta concentração do ingrediente ativo, além deapresentar um ingrediente ativo derivado de um precursor fitotóxico, o que reduza aplicação deste material como um bom fungicida.USPTO 4514225 discloses the preparation and use of an acetylsalicylate-derived compostotriorganate for the control of microorganismostals such as bacteria, algae, marine organisms as well as wood preservation. Metal precursors of general formula SnCIR3 (R = butyl, phenyl, alkyl and cyclohexyl) were used in the preparation of the active compounds. Compost may be applied in solution, emulsion, dispersions in water or through organic solvents. The compounds described in this patent may be applied in combination with other biocidal activity compounds. The disadvantage of this invention relates to the high concentration of the active ingredient, besides having an active ingredient derived from a phytotoxic precursor, which reduces application of this material as a good fungicide.
A patente USPTO 4221811 relata o efeito fungicida, bactericida e processode controle de fungos e bactéria de triorganoestânicos contendo grupossubstituintes tais como fenil-, butil-, metilbutil-, metilfenil- ligados ao centrometálico com até dois centros metálicos onde o quarto grupo substituinte ligadoao centro metálico consiste de grupos -OH, -CN, dimetilaminopropilamina (-NH(CH2)3-NMe2) ou o hidrocloreto correspondente (-NH(CH2)3-NMe2.2HCI). Oscompostos apresentaram atividade contra fungos, bactérias gram-posistivas egram-negativas. Nesta patente fica evidenciado que a solubilidade do compostoativo em água promove fortemente a sua atividade fungicida e bactericida. O usode solventes orgânicos na aplicação dos produtos ativos tem algumasdesvantagens, como serem voláteis, inflamáveis e tóxicos. A invenção emquestão apresenta a desvantagem de ter um alto valor do MIC (ConcentraçãoMínima Inibitória). O presente pedido de patente se diferencia desta patente pelobaixo valor do MIC, bem como pelo uso de diferente precursor orgânico, a 4,6-dimetil-2-mercaptopirimidina.USPTO 4221811 discloses the fungicidal, bactericidal and process effect of fungal and bacterial triorganoic control bacteria containing substituents such as phenyl-, butyl-, methylbutyl-, methylphenyl- linked to the centrometal with up to two metal centers where the fourth substituent group is attached to the metal center. It consists of -OH, -CN, dimethylaminopropylamine (-NH (CH2) 3-NMe2) or the corresponding hydrochloride (-NH (CH2) 3-NMe2.2HCl) groups. The compounds showed activity against fungi, gram-negative egram-negative bacteria. It is apparent from this patent that the solubility of the compound in water strongly promotes its fungicidal and bactericidal activity. The use of organic solvents in the application of active products has some disadvantages, such as being volatile, flammable and toxic. The present invention has the disadvantage of having a high MIC (Minimum Inhibitory Concentration) value. The present patent application differs from this patent by the low value of the MIC as well as the use of different organic precursor, 4,6-dimethyl-2-mercaptopyrimidine.
Outros compostos isentos de estanho, porém contendo em suacomposição química átomos de enxofre e nitrogênio, também são fungicidascomo descrito na patente USPTO 7067668. Esta invenção relata o potencialfungicida de derivados do 4-quinolinol na agricultura e horticultura. Os compostosativos apresentaram uma atividade contra fungos patogênicos de plantas comoarroz (blast), feijão (brown spot) e batata (antracnose). Entretanto, esta invençãoapresenta a desvantagem de utilizar alta concentração do ingrediente ativo.Other tin-free compounds, but containing in their chemical composition sulfur and nitrogen atoms, are also fungicidal as described in USPTO 7067668. This invention reports the fungicidal potential of 4-quinolinol derivatives in agriculture and horticulture. The compounds showed an activity against pathogenic fungi of plants such as rice (blast), beans (brown spot) and potato (anthracnose). However, this invention has the disadvantage of using high concentration of the active ingredient.
As patentes USPTO 6270810, USPTO 6267991, USPTO 6264993,USPTO 6075047, USPTO 6060490, USPTO 6057356, USPTO 6004947 relatama aplicação de composição fungicida contendo um ou mais princípios ativos, porexemplo, a N-acetonilbenzamida adicionada a outro(s) antifúngico(s) que atuamcomo inibidor da respiração, como o ziram e fluazinam. A N-acetonilbenzamidapode também ser adicionada a um metabólito fungitóxico a base de estanho, porexemplo, fentin (hidróxido de trifenilestanho ou acetato de trifenilestanho). Adesvantagem destas invenções refere-se ao caráter fitotóxico do ingredienteativo.USPTO 6270810, USPTO 6267991, USPTO 6264993, USPTO 6075047, USPTO 6060490, USPTO 6057356, USPTO 6004947 discloses application of fungicidal composition containing one or more active ingredients, for example, antifungal N-acetonylbenzamide (s) that act as a breath inhibitor such as ziram and fluazinam. N-acetonylbenzamid may also be added to a tin-based fungitoxic metabolite, for example, fentin (triphenyltin hydroxide or triphenyltin acetate). The advantage of these inventions relates to the phytotoxic character of the reactive ingredient.
A patente USPTO 4554367 relata a aplicação dehalogenoorganoestanatos(IV) de fosfônio como agentes biocidas, bem como paraa preservação de materiais e proteção de várias culturas na agricultura. Oscomplexos de fosfônio estanatos(IV) se destacam pela sua alta solubilidade emágua, pouco volátil e atividade biocida. A principal aplicação desta invenção estárelacionada ao uso deste material como tinta protetora. Esta invenção apresentaa desvantagem de ter um alto valor do MIC (Concentração Mínima Inibitória).USPTO 4554367 discloses the application of phosphonium halogenene stannates (IV) as biocidal agents as well as for the preservation of materials and protection of various crops in agriculture. Phosphonium stannate (IV) complexes stand out for their high water solubility, low volatility and biocidal activity. The main application of this invention relates to the use of this material as a protective paint. This invention has the disadvantage of having a high MIC (Minimum Inhibitory Concentration) value.
A patente USPTO 4474760 relata a atividade de mistura de compostoscontendo uma combinação de 2-mercaptopiridina-1-oxo ou derivado(trifenilestanho-2-mercaptopiridina-1-oxo), um organofosforado, por exemplo,difenilisodecilfosfito, entre outros e, um benzotriazol, por exemplo, 2-(2'-hidroxi-5-t-octilfenil)benzotriazol. As várias combinações antimicrobianas • sãoestabilizadoras de sistemas poliméricos, podendo ser utilizadas para proteção deadesivos, folhas de filmes e qualquer sistema polimérico baseado em materiaiscomo cloreto de polivinil, copolímero cloreto de vinila-acetato de vinila,acrilonitrila-butadieno-stireno (ABS), poliuretano, entre outros. Entretanto estainvenção apresenta a desvantagem de utilizar alta concentração do ingredienteativo, bem como apresentar um resultado fungicida limitado de baixo espectro deação, além de o ingrediente ativo decompor por ação do calor.USPTO 4474760 discloses compound mixing activity containing a combination of 2-mercaptopyridine-1-oxo or derivative (triphenyltin-2-mercaptopyridine-1-oxo), an organophosphate, for example diphenylisodecylphosph, among others, and a benzotriazole, for example 2- (2'-hydroxy-5-t-octylphenyl) benzotriazole. The various antimicrobial combinations are stabilizing for polymeric systems and can be used for protection against adhesives, film sheets and any polymeric system based on materials such as polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, acrylonitrile-butadiene-styrene (ABS), polyurethane , among others. However, this invention has the disadvantage of using high concentration of the active ingredient, as well as presenting a limited fungicidal result of low spectrum, besides the active decomposition by heat action.
Várias das patentes mencionadas abaixo relatam o uso de compostosorgânicos com atividade biocida. Estes compostos são misturados a fungicidasconhecidos de estanho ou de outro metal para comporem uma formulação ativa.A composição final da mistura pode conter um ou mais princípios ativos demetais distintos. Alguns exemplos são mancozeb, brestan, benomil e fentin(hidróxido de trifenilestanho e acetato de trifenilestanho). Além disso, a naturezaquímica do material orgânico é completamente diferente do apresentado napresente invenção, objeto de pedido de patente. Outras patentes envolvendocompostos de estanho estão relacionadas a outro tipo de aplicação destesmateriais e mais uma vez têm a natureza química diferente da presente invençãono que se refere ao precursor orgânico: USPTO 7316738, USPTO 7194964,USPTO 7070795, USPTO 6811703, USPTO 6624179, USPTO 6399542, USPTO6303078, USPTO 6291399, USPTO 5952496, USPTO 5939357, USPTO5910496, USPTO RE35985, USPTO 5436267, USPTO 5346704, USPTO5338551, USPTO 5306712, USPTO 5384844, USPTO 5262414, USPTO5157028, USPTO 5134152, USPTO 5131947, USPTO 5118346, USPTO H811,USPTO 4923866, USPTO 4766113, USPTO 4710220, USPTO 4666767, USPTO4639393, USPTO 46020.11, USPTO 4353962, USPTO 4528228, USPTO4286020, USPTO 4276308, USPTO 4275079, USPTO 4169902, USPTO4160335, USPTO 4141989, USPTO 4107323, USPTO 4094845, USPTO4051255, USPTO 3984568, USPTO 3979518, USPTO 4125624, USPTO3957847, USPTO 3954992, USPTO 3932448, USPTO 5468715, USPTO4482759.Several of the patents mentioned below report the use of organic compounds with biocidal activity. These compounds are mixed with known tin or other metal fungicides to form an active formulation. The final composition of the mixture may contain one or more active ingredients of different metals. Some examples are mancozeb, brestan, benomyl and fentin (triphenyltin hydroxide and triphenyltin acetate). Furthermore, the chemical nature of the organic material is completely different from that disclosed in the present invention, the subject of patent application. Other patents involving tin compounds are related to another type of application of these materials and again have the different chemical nature of the present invention in relation to the organic precursor: USPTO 7316738, USPTO 7194964, USPTO 7070795, USPTO 6811703, USPTO 6624179, USPTO 6399542, USPTO 6303078, USPTO 6291399, USPTO 5952496, USPTO 5939357, USPTO5910496, USPTO RE35985, USPTO 5436267, USPTO 5346704, USPTO 5336751, USPTO 5306712, USPTO 5384844, USPTO 5262115, USPTO USPTO 4766113, USPTO 4710220, USPTO 4666767, USPTO4639393, USPTO 46020.11, USPTO 4353962, USPTO 4528228, USPTO4286020, USPTO 4276308, USPTO 4275079, USPTO 4169902, USPTO41640445, 409 USPTO 4125624, USPTO3957847, USPTO 3954992, USPTO 3932448, USPTO 5468715, USPTO4482759.
A presente invenção, objeto do presente pedido de patente, consiste decomposto de coordenação organoestânico derivado da reação entre o cloreto detrifenilestanho(IV) com o bis-(4,6-dimetil-2-mercaptopirimidil)-etano. A análise daspatentes supracitadas revela claramente que o composto, objeto do presentepedido de patente, é completamente diferente, tanto em natureza química comoem fórmula química. Por exemplo, o precursor orgânico 2,5-dimetilbenzotiol diferedo bis-(4,6-dimetil-2-mercaptopirimidil)-etano por não conter nitrogênio em suacomposição química, além do fato deste último apresentar dois grupos 4,6-dimetil-2-pirimidil, bem como dois grupos CH2 entre os átomos de enxofre. Ocomposto organoestânico derivado da reação com o 2,5-dimetilbenzotiol terá, poristo mesmo, uma estrutura e fórmula química distinta do composto, objeto dopresente pedido de patente. O presente composto, objeto do pedido de patente, étambém totalmente diferente quanto à estrutura e composição química defungicidas conhecidos e comercializados, como o hidróxido de trifenilestanho(IV)e o acetato de trifenilestanho(IV), bem como de todos aqueles citados empatentes de bancos de dados nacionais e internacionais. Por exemplo, comocitado acima, o composto derivado da reação entre o cloreto de trifenilestanho eo 2,5-dimetilbenzotiol (UPSTO 4678804) não terá ligações químicas entre oátomo de estanho e o átomo de nitrogênio, o que necessariamente implica emcomposto de natureza química completamente distinta do composto objeto dopresente pedido de patente.The present invention, object of the present patent application, consists of organotin coordination coordination derived from the reaction between detriphenyl tin (IV) chloride and bis (4,6-dimethyl-2-mercaptopyrimidyl) -ethane. Analysis of the above patents clearly reveals that the compound subject to the present patent application is completely different, both in chemical nature and in chemical formula. For example, the organic precursor 2,5-dimethylbenzothiol differs from bis- (4,6-dimethyl-2-mercaptopyrimidyl) -ethane in that it does not contain nitrogen in its chemical composition, besides the fact that the latter has two groups 4,6-dimethyl-2 -pyrimidyl, as well as two CH2 groups between sulfur atoms. The organotin compound derived from the reaction with 2,5-dimethylbenzothiol will therefore have a structure and chemical formula distinct from the compound, object of this patent application. The present application, which is the subject of the patent application, is also totally different in its known and marketed chemical fungicidal structure and chemical composition, such as triphenyltin (IV) hydroxide and triphenyltin acetate (IV), as well as all those mentioned bank empaths. national and international data. For example, as noted above, the compound derived from the reaction between triphenyltin chloride and 2,5-dimethylbenzothiol (UPSTO 4678804) will have no chemical bond between the tin atom and the nitrogen atom, which necessarily implies a completely distinct chemical compound. of the object compound of the present patent application.
O combate a fungos fitopatogênicos em plantas é um problema mundialque determina sobremaneira a sobrevivência humana e o desenvolvimentosocial. Várias patentes descrevem a preparação de derivados organoestânicospara o combate a doenças de plantas como ingredientes em composiçãofungicida, inseticida e bactericida. Entretanto, vários problemas como resistênciados fungos, alto valor do MIC (Concentração Mínima Inibitória), altasconcentrações do ingrediente ativo, estimulam o desenvolvimento de novosfungicidas para o controle de doenças em plantas. A presente invenção tem porobjetivo o desenvolvimento de novo composto fungicida eficaz no controle dedoenças de plantas, e outros fungos toxicogênicos e alergênicos, com baixatoxicidade, baixo valor do MIC e baixa concentração do ingrediente ativo comamplo espectro de ação.Combating phytopathogenic fungi in plants is a worldwide problem that greatly determines human survival and social development. Several patents describe the preparation of organostannic derivatives for combating plant diseases as ingredients in fungicidal, insecticidal and bactericidal composition. However, several problems such as fungal resistance, high MIC (Minimum Inhibitory Concentration) value, high active ingredient concentrations, stimulate the development of new fungicides for plant disease control. The present invention aims to develop a novel fungicidal compound effective in the control of plant diseases, and other toxicogenic and allergenic fungi, with low toxicity, low MIC value and low active ingredient concentration with broad spectrum of action.
O material orgânico precursor, bis-(4,6-dimetil-2-mercaptopirimidil)-etanoou bis-(4,6-dimetil-2-pirimidiltio)-etano, não possui atividade fungicida oufungistática. Com a introdução do precursor metálico, cloreto detrifenilestanho(IV), como parte da composição química do bis-(4,6-dimetil-2-mercaptopirimidil)-etano, a atividade biológica do novo composto, objeto depedido de patente, foi verificada para vários fungos. A solubilidade do compostoem solventes de classificação química variada viabiliza a sua aplicação como pó,spray, em solução ou emulsão no setor de agricultura durante o cultivo earmazenamento de frutas e sementes na pós-colheita.The precursor organic material, bis- (4,6-dimethyl-2-mercaptopyrimidyl) -ethane or bis- (4,6-dimethyl-2-pyrimidylthio) -ethane, has no fungicidal or fungicidal activity. With the introduction of the metal precursor, detriphenyl tin (IV) chloride, as part of the chemical composition of bis- (4,6-dimethyl-2-mercaptopyrimidyl) -ethane, the biological activity of the new patent-pending compound was verified to Various fungi. The solubility of the compound in solvents of varying chemical classification enables its application as a powder, spray, solution or emulsion in the agriculture sector during cultivation and postharvest fruit and seed storage.
O composto, objeto do presente pedido de patente, difere das patentesUSPTO 4581373, USPTO 4514225, USPTO 42221811, USPTO 6270810,USPTO 4115094, USPTO 5436267, USPTO 4654368, uma vez que pode seraplicado como único princípio ativo e ainda apresenta a vantagem de uso emmenores doses, com maior eficiência e menor risco ambiental. O composto,objeto de pedido de patente, não apresenta fltotoxicidade como o fungicidahidróxido de trifenilestanho(IV) e acetato de trifenilestanho(IV) com relação àconcentração do mesmo em formulações. Além disto, o composto e derivado,objeto de pedido de patente, decompõem para resíduos não tóxicos por ação daluz e são eficazes mesmo em meio ácido, podendo ser aplicados em solos deacidez variada para várias culturas de produtos agrícolas. Portanto, o compostoobjeto de pedido de patente, é uma novidade tanto do ponto de vista da Químicaquanto da eficácia biológica para o combate a fungos fitopatogênicos. Ocomposto pode ser utilizado no cultivo de frutas como a banana, mamão e grãoscomo o trigo, bem como no armazenamento destes. O composto pode ainda serusado para formulação de fungicida, inseticida, herbicida, acaricida, pesticida oubactericida, bem como princípio ativo único ou em mistura com os princípiosativos já existentes para melhorar sua eficácia. As formulações podem sersólidas, líquidas ou gasosas com o uso de veículos inertes tais como talco ouágua para o combate a organismos patogênicos e outros de origem animal ouvegetal. A presente invenção, objeto do presente pedido de patente, é eficaz nocontrole de doenças de plantas e outros fungos toxicogênicos e alergênicosapresentando vantagens em relação aquelas supracitadas. Por exemplo, baixatoxicidade, baixo valor do MIC, baixa concentração do ingrediente ativo, amploespectro de ação e menos agressiva ao meio ambiente, em razão dadecomposição do composto ativo no solo levar a formação de subprodutos nãotóxicos.The compound, subject of the present patent application, differs from patentsUSPTO 4581373, USPTO 4514225, USPTO 42221811, USPTO 6270810, USPTO 4115094, USPTO 5436267, USPTO 4654368 as it may be applied as the sole active ingredient and still has the advantage of use. doses, with higher efficiency and lower environmental risk. The compound under patent application does not exhibit phtotoxicity such as triphenyltin (IV) fungicide hydroxide and triphenyltin (IV) acetate with respect to its concentration in formulations. In addition, the compound and derivative, subject to patent application, decompose to non-toxic residues by light action and are effective even in acid medium and can be applied in soils of varying acidity for various crops of agricultural products. Therefore, the object compound of patent application is new both from the point of view of Chemistry and its biological efficacy to combat phytopathogenic fungi. The compound can be used for growing fruits such as bananas, papaya and grains such as wheat, as well as for storing them. The compound may also be used for the formulation of fungicide, insecticide, herbicide, acaricide, pesticide or bactericide as well as a single active ingredient or in admixture with existing principles to improve its effectiveness. The formulations may be solid, liquid or gaseous using inert vehicles such as talc or water to combat pathogenic and other organisms of animal origin. The present invention, object of the present patent application, is effective in the control of plant diseases and other toxicogenic and allergenic fungi presenting advantages over those mentioned above. For example, low toxicity, low MIC value, low concentration of active ingredient, broad spectrum of action, and less aggressive to the environment, because the composition of the active compound in the soil leads to the formation of non-toxic by-products.
Descrição da invençãoDescription of the invention
A presente invenção, objeto de pedido de patente, trata de compostoorganoestânico com ação fungicida contra fungos fitopatogênicos, toxicogênicose alergênicos de plantas, frutos e sementes para aplicação no cultivo de produtosagrícolas e na pós-colheita. A preparação do material orgânico precursor dapresente invenção, bis-(4,6-dimetil-2-mercaptopirimidil)-etano ou bis-(4,6-dimetil-2-pirimidiltio)-etano, seguiu o procedimento descrito na Técnica 1. A preparaçãodo material organoestânico da presente invenção envolve duas técnicas: Técnica2 e a Técnica 3.Descrição detalhada da invençãoThe present invention, which is the subject of a patent application, deals with a fungicidal organotin compound against phytopathogenic fungi, toxicogens and allergens from plants, fruits and seeds for application in the cultivation of agricultural products and postharvest. The preparation of the precursor organic material of the present invention, bis- (4,6-dimethyl-2-mercaptopyrimidyl) -ethane or bis- (4,6-dimethyl-2-pyrimidylthio) -ethane, followed the procedure described in Art 1. Preparation of the organotin material of the present invention involves two techniques: Technique 2 and Technique 3. Detailed Description of the Invention
Técnica 1:Technique 1:
Em um recipiente adequado, de preferência um balão de fundo redondo,foi colocado 12 a 90 ml_ de etanol, e depois adicionado 1,7 a 100 mmol de 4,6-dimetil-2-mercaptopirimidina e 1,5 a 251,6 mmol de KOH. Após a dissolução dossólidos, acrescentou-se 1,3 a 102,3 mmol de dibromoetano. A mistura foi mantidasob agitação e refluxo por 0,5 a 5,5 horas. Em seguida, a solução resultante decoloração laranja, foi vertida em um Becker contendo gelo moído a qual foimantida em geladeira de 4 a 24 horas. Após este período um precipitado amarelose separou no meio aquoso, o bis-(4,6-dimetil-2-mercaptopirimidil)-etano. Oprecipitado foi filtrado e lavado com 100 a 1000 mL de água gelada e, emseguida, com 50 a 150 mL de n-hexano. O composto resultante é solúvel emsolventes orgânicos usuais tais como diclorometano, metanol, etanol, acetonitrilae acetona.In a suitable container, preferably a round bottom flask, 12 to 90 ml of ethanol was placed, and then 1.7 to 100 mmol of 4,6-dimethyl-2-mercaptopyrimidine and 1.5 to 251.6 mmol were added. of KOH. After dissolution of the solids, 1.3 to 102.3 mmol of dibromoethane was added. The mixture was kept under stirring and reflux for 0.5 to 5.5 hours. Then the resulting orange-colored solution was poured into a crushed ice-containing Becker which was kept in a refrigerator for 4 to 24 hours. After this period a yellowish precipitate separated in the aqueous medium, bis- (4,6-dimethyl-2-mercaptopyrimidyl) -ethane. The precipitate was filtered and washed with 100 to 1000 mL of ice water and then 50 to 150 mL of n-hexane. The resulting compound is soluble in usual organic solvents such as dichloromethane, methanol, ethanol, acetonitrile and acetone.
Técnica 2:Technique 2:
Em um recipiente adequado, de preferência um tubo de Schlenckdesaerado previamente e mantido sob atmosfera inerte de nitrogênio ou argônio,foi acrescentado 1,05 a 52,3 mmol de cloreto de trifenilestanho(IV), dissolvido emquantidade suficiente de diclorometano, podendo-se usar qualquer outro solventeclorado. Sobre esta solução, acrescentou-se 0,2 a 11,6 mmol de bis-(4,6-dimetil-2-mercaptopirimidil)-etano, objeto sintetizado na Técnica 1. A mistura pode serdeixada sob agitação em atmosfera inerte de 1,5 a 3,5 horas. Em seguida ovolume foi reduzido em linha de vácuo obtendo-se um material amarelo-claro. Omaterial resultante é lavado ao ar com n-hexano e guardado em ambiente secosob vácuo.In a suitable container, preferably a previously prepared Schlenck tube maintained under an inert atmosphere of nitrogen or argon, 1.05 to 52.3 mmol of triphenyltin (IV) chloride, dissolved in sufficient amount of dichloromethane, was added. any other chlorinated solvent. To this solution, 0.2 to 11.6 mmol of bis- (4,6-dimethyl-2-mercaptopyrimidyl) -ethane, object synthesized in Art 1, was added. The mixture may be left under stirring in an inert atmosphere of 1, 5 to 3.5 hours. Then the volume was reduced under vacuum to give a light yellow material. The resulting material is air washed with n-hexane and stored in a dry environment under vacuum.
O composto também pode ser obtido deixando a mistura para evaporaçãolenta do solvente ao ar, de maneira que com a redução da metade do solvente naprimeira precipitação, o material amarelo-claro é filtrado, lavado ao ar com n-hexano e guardado sob vácuo. O composto químico, objeto do pedido depatente, é parcialmente solúvel em hidrocarbonetos, mas solúvel em solventesclorados como clorofórmio, éteres, sulfóxidos, amidas, nitrilas, alcoóis, cetonas eem mistura água/álcool.The compound can also be obtained by leaving the mixture for slow evaporation of the solvent in air, so that by reducing half of the solvent in the first precipitation, the light yellow material is filtered, air washed with n-hexane and stored under vacuum. The chemical subject of the application is partially soluble in hydrocarbons but soluble in chlorinated solvents such as chloroform, ethers, sulfoxides, amides, nitriles, alcohols, ketones and in a water / alcohol mixture.
Técnica 3:Technique 3:
O composto, objeto do pedido de patente, também pode ser preparado noestado sólido nas mesmas condições descritas na Técnica 2. Em um tubo deSchlenck foi colocado de 1,01 a 50,3 mmol de cloreto de trifenilestanho(IV) e 0,2a 11,6 mmol de bis-(4,6-dimetil-2-mercaptopirimidil)-etano. A mistura é aquecidaentre 40 a 100 graus Celsius, mantendo-se o sistema em atmosfera inerte denitrogênio ou argônio por um período de 1,5 a 3,5 horas. Após este período, otubo foi resfriado e o material sólido foi retirado e guardado em ambiente secosob vácuo. As mesmas propriedades de soiubiiidade foram observadas para ocomposto preparado via a Técnica 2, ou seja, parcialmente solúvel emhidrocarbonetos, mas solúvel em solventes clorados como clorofórmio, éteres,sulfóxidos, amidas, nitrilas, alcoóis, cetonas e em mistura água/álcool.The compound under patent application can also be prepared in the solid state under the same conditions as described in Art 2. In a Schlenck tube, 1.01 to 50.3 mmol triphenyltin (IV) chloride and 0.2 to 11 were placed. Bis (4,6-dimethyl-2-mercaptopyrimidyl) -ethane, 6 mmol. The mixture is heated to 40 to 100 degrees Celsius, maintaining the system in an inert atmosphere of denitrogen or argon for a period of 1.5 to 3.5 hours. After this time, the tube was cooled and the solid material was removed and stored in a dry environment under vacuum. The same solubility properties were observed for the compound prepared via Technique 2, ie partially soluble in hydrocarbons but soluble in chlorinated solvents such as chloroform, ethers, sulfoxides, amides, nitriles, alcohols, ketones and water / alcohol mixture.
A caracterização da presente invenção envolveu vários métodos analíticose espectroscópicos, os quais confirmaram a ligação química do estanho aosátomos de carbono, nitrogênio e cloro no estado sólido, estabelecendo apentavalência do átomo de estanho. Em solução, um único sinal de RMN de119Sn foi observado dentro de uma faixa atribuída comumente tanto a estanhopentavalente como tetravalente. Neste contexto, a presente invenção em soluçãopode ter todos os átomos de estanho pentavalentes, todos os átomos de estanhotetravalentes ou na razão pentavalente/tetravalente de 1:1, 1:2, 1:3 e 2:2 ou aindana razão tetravalente/pentavalente de 1:2 e 1:3.The characterization of the present invention involved several spectroscopic analytical methods, which confirmed the chemical binding of tin to solid state carbon, nitrogen and chlorine atoms, establishing tin atom apentavalence. In solution, a single 119Sn NMR signal was observed within a range commonly assigned to both the tidal and tetravalent tin. In this context, the present invention in solution may have all pentavalent tin atoms, all tinravalent atoms or in the pentavalent / tetravalent ratio of 1: 1, 1: 2, 1: 3 and 2: 2 or even tetravalent / pentavalent ratio of 1: 2 and 1: 3.
Experimento de Demonstração:Demonstration Experiment:
O composto sintetizado por Técnica 2 e/ou 3 foi testado para determinarsua atividade fungicida, através de experimentos de teste de germinação deesporos e de crescimento micelial in vitro com uso de 12 tipos de fungosfisiologicamente diferentes, representando fungos fitopatogênicos, alergênicos etoxicogênicos. A solução estoque de composto foi preparada em metanol.The compound synthesized by Technique 2 and / or 3 was tested to determine its fungicidal activity through in vitro spore germination and mycelial growth testing experiments using 12 different physiologically different types of fungi, representing phytopathogenic, allergic ethoxycogenic fungi. Compound stock solution was prepared in methanol.
Experimento 1Para que ocorra a doença nas plantas causada por um fungo, sãonecessários que os conídios/esporos deste fungo fitopatogênico germinem. Seestes esporos não germinarem, por qualquer causa, não haverá ocorrência dadoença, e assim não haverá prejuízo ao agricultor. Este experimento foi feito parademonstrar o efeito fungicida nos esporos/conídios de fungos, utilizando a técnicapadrão de "alimento venenoso". A solução estoque do composto, objeto depedido de patente, foi adicionada no meio de cultura czepeck-Dox agaresterilizado, para obter as concentrações finais de 0,1 a 6 ppm. O meio de culturasem o composto serviu de testemunha. Foram espalhados na superfície do meiode cultura os conídios/esporos de usos teste, em cada placa. Após 48h deincubação foi contado o número de conídios/esporos germinados em cadaconcentração do novo composto e comparado com a germinação no meio decultura sem o composto. O efeito fungicida foi determinado, calculando-se apercentagem de conídios/esporos mortos em relação à testemunha.Experiment 1 For plant disease caused by a fungus to occur, it is necessary that the conidia / spores of this phytopathogenic fungus germinate. If these spores do not germinate for any cause, no disease will occur, and thus no harm to the farmer. This experiment was conducted to demonstrate the fungicidal effect on fungal spores / conidia using the standard "poisonous food" technique. The stock solution of the patent-pending compound was added to the czepeck-Dox agar sterilized culture medium to obtain final concentrations of 0.1 to 6 ppm. The culture medium in the compound served as a witness. The test uses conidia / spores were spread on the middle of the culture medium on each plate. After 48h of incubation, the number of conidia / spores germinated in each concentration of the new compost was counted and compared to the germination in the culture medium without the compost. The fungicidal effect was determined by calculating the percentage of dead conidia / spores relative to the control.
Resultados: Os resultados de efeito mortal nos esporos/conídios destenovo composto fungicida, objeto de pedido de patente, são apresentados naTABELA 1. É evidente que o composto foi fungitóxico para os esporos/conídiosde todas as espécies testadas nas dosagens variando de 0,1 a 6 ppm,dependendo do fungo. O composto teve efeito mortal diferente em diferentesfungos, sendo que o composto foi mais tóxico ao P. grisea causador de brusonede arroz e de trigo, causando mortalidade de 100% de conídios na dose de 0,2ppm, e ainda na dose de 0,1 ppm, houve mortalidade de 97% de conídios. Ocomposto teve um efeito na mortalidade de 100% de conídios/esporos de fungosAl. solani, causador de pinta preta de tomate e batata, Al. Brassicicola, causadorde requeima de repolho, couve-flor, brócolis e plantas afins, C. gloeosporioides,causador de antracnose de várias espécies de plantas economicamenteimportantes e de podridão de frutas e legumes em pós-colheita, C. musae,causador de antracnose de banana e podridão pós-colheita de banana, B.sorokiniana, causador de requeima de espigueta de trigo, cevada, arroz, na dosede 2 a 3ppm. Para os fungos toxicogênicos e alergênicos como A. ochraceus, A.glaucus e A. flavus, o composto causou mortalidade de 100% deconídios/esporos na dose de até 1 ppm. Para os fungos causadores de podridãode raiz e de frutas e legumes, o F semitectum e F. graminearum, o compostocausou 100% de mortalidade na concentração de 6 ppm. Estes resultadosmostram que o novo composto, objeto de pedido de patente, é um composto compropriedade fungicida de amplo espectro.Results: The results of the deadly effect on spores / conidia of this fungicidal compound subject to patent application are presented in TABLE 1. It is evident that the compound was spore / conidial fungotoxic of all species tested at dosages ranging from 0.1 to 6 ppm, depending on the fungus. The compound had different deadly effect in different fungi, and the compound was more toxic to P. grisea causing rice and wheat blast, causing 100% conidial mortality at 0.2 ppm, and at 0.1 dose. ppm, there was a 97% conidial mortality. The compound had an effect on the 100% mortality of Al fungal conidia / spores. solani, cause of tomato and potato black spot, Al. Brassicicola, cause of late blight of cabbage, cauliflower, broccoli and related plants, C. gloeosporioides, cause of anthracnose of various economically important plant and fruit and vegetable rot species. postharvest, C. musae, cause of banana anthracnose and rot Postharvest of banana, B.sorokiniana, cause of wheat spike, barley, rice blight, in the dose 2 to 3ppm. For toxicogenic and allergenic fungi such as A. ochraceus, A.glaucus and A. flavus, the compound caused mortality of 100% deconides / spores up to 1 ppm. For root and fruit rot fungi, F semitectum and F. graminearum, compost caused 100% mortality at a concentration of 6 ppm. These results show that the new compound, which is the subject of a patent application, is a broad spectrum fungicidal property compound.
TABELA 1: Mortalidade de conídios/esporos de fungos fitopatogênicos,toxicogênicos e alergênicos causada pelo composto objeto de pedido de patente,nas diferentes doses/concentrações.TABLE 1: Mortality of phytopathogenic, toxicogenic and allergenic fungi conidia / spores caused by the compound subject to patent application, at different doses / concentrations.
Percentagem de mortalidade dos conídios in vitro/Concentração (ug.mL1)In vitro conidia mortality percentage / Concentration (µg.mL1)
<table>table see original document page 14</column></row><table><table> table see original document page 14 </column> </row> <table>
* Não testado. Media de três repetições.Experimento 2* Not tested. Average of three repetitions. Experiment 2
Para que ocorra a doença nas plantas causada por um fungo sãonecessários que os conídios/esporos deste fungo fitopatogênico germinem e hácrescimento de micélio que vai invadir os tecidos das plantas. Este experimentofoi feito para demonstrar efeito fungitóxico que impede o crescimento dos fungos.Foi utilizada a técnica padrão de "alimento venenoso". A solução estoque docomposto, objeto de pedido de patente, foi adicionada no meio de culturaczepeck-Dox agar esterilizado, para obter as concentrações finais de 0,1 a 6ppm. O meio de cultura sem o composto serviu de testemunha. O meio foisemeado no centro em cada placa, com um disco de 5 mm de cultura dorespectivo fungo. As culturas foram incubadas até que o crescimento do fungo-teste atingisse as bordas das placas. Foi então medido o diâmetro da colônia defungos em placa contendo o composto. O efeito fungicida foi determinado,calculando-se a percentagem de inibição de crescimento do fungo em relação àtestemunha.For plant disease caused by a fungus to occur, it is necessary that the conidia / spores of this phytopathogenic fungus germinate and there is mycelium growth that will invade plant tissues. This experiment was done to demonstrate fungitoxic effect that prevents fungal growth. The standard technique of "poisonous food" was used. The compounded stock solution under patent application was added to the sterile culturaczepeck-Dox agar medium to obtain the final concentrations of 0.1 to 6ppm. The culture medium without the compound served as a control. The medium was centered on each plate with a 5 mm disc of dormant fungus culture. The cultures were incubated until the growth of the test fungus reached the edges of the plates. The diameter of the plate-containing fungi colony was then measured. The fungicidal effect was determined by calculating the percentage inhibition of fungal growth relative to the control.
Resultados: Os resultados do efeito deste novo composto fungicida, objetode pedido de patente, são apresentados na TABELA 2. É evidente que ocomposto foi fungitóxico para todas as espécies testadas na dosagem variável de0,1 a 6 ppm, dependendo do fungo. O novo composto na dose de 0,2 ppm inibiucompletamente o crescimento de P. grísea, causador de brusone de arroz e trigo,e ainda na dose de 0,1 ppm houve 97% de inibição. Al. solani, causador de pintapreta de tomate e batata, Al. Brassicicola, causador de requeima de repolho,couve-flor, brócolis e plantas afins, C. gloeosporioides, causador de antracnosede várias espécies de plantas economicamente importantes e de podridão defrutas e legumes em pós-colheita, C. musae, causador de antracnose e podridãopós-colheita de banana, B. sorokiniana, causador de requeima de espigueta detrigo, cevada e arroz foram completamente inibidos na dose de 2 a 3ppm. Ocrescimento dos fungos toxicogênicos como A. ochraceus e A. glaucus foi inibidocompletamente na dose de até 1 ppm. Para os fungos causadores de podridãode raiz, frutas e legumes, o F. semitectum e F. graminearum, o composto causou100% de inibição na dose de 6 ppm. Estes resultados mostram que o novocomposto, objeto de pedido de patente, é um composto com propriedadefungicida de amplo espectro.Results: The results of the effect of this new fungicidal compound, object of patent application, are presented in TABLE 2. It is evident that the compound was fungitoxic for all species tested at a variable dosage of 0.1 to 6 ppm, depending on the fungus. The new compound at the 0.2 ppm dose completely inhibited the growth of P. grísea, which caused rice and wheat blast, and at the 0.1 ppm dose there was 97% inhibition. Al. Solani, cause of black tomato and potato pint, Al. Brassicicola, cause of late blight of cabbage, cauliflower, broccoli and related plants, C. gloeosporioides, cause of anthracnosede several species of economically important plants and rot fruits and vegetables in postharvest, C. musae, anthracnose and rotten after banana harvest, B. sorokiniana, detrigo, barley and rice late blight were completely inhibited at 2 to 3ppm. The growth of toxicogenic fungi such as A. ochraceus and A. glaucus was completely inhibited at a dose of up to 1 ppm. For the root rot fungi, fruits and vegetables, F. semitectum and F. graminearum, the compound caused 100% inhibition at 6 ppm. These results show that the new compound, the subject of patent application, is a broad spectrum fungicidal property compound.
TABELA 2: Inibição de crescimento micelial de fungos fitopatogênicos,toxicogênicos e alergênicos causado pelo composto objeto de pedido de patente,nas diferentes doses/concentrações.TABLE 2: Inhibition of mycelial growth of phytopathogenic, toxicogenic and allergenic fungi caused by the compound under patent application at different doses / concentrations.
<table>table see original document page 15</column></row><table><table>table see original document page 16</column></row><table><table> table see original document page 15 </column> </row> <table> <table> table see original document page 16 </column> </row> <table>
Os resultados experimentais demonstram claramente o efeito fungicida dapresente invenção, objeto de pedido de patente, que pode ser utilizado paraformular novo fungicida misturando-o com veículo inerte sólido, por exemplo, masnão limitados ao talco, caulin, bentonita, ou outras argilas; misturando-o comveículo inerte líquido, por exemplo, mas não limitado a solventes orgânicos, óleosde origem vegetal, animal ou mineral. Dependendo do uso final do novocomposto, objeto de pedido de patente, pode ser adicionado um espalhanteadesivo de acordo com a disponibilidade do material inerte e o estado da artedisponível para o controle de doenças das plantas e seus produtos.The experimental results clearly demonstrate the fungicidal effect of the present invention, which may be used to formulate novel fungicide by mixing it with solid inert carrier, for example, but not limited to talc, kaolin, bentonite, or other clays; mixing it with a liquid inert carrier, for example, but not limited to organic solvents, oils of vegetable, animal or mineral origin. Depending on the end use of the new compound, which is the subject of a patent application, a spreader may be added according to the availability of inert material and the condition available for disease control of plants and their products.
Analogamente o mesmo pode ser feito para eliminação de fungos toxicogênicos ealergênicos em dosagens muito baixas. O composto e seus derivados, objeto depedido de patente, pode ser misturado com os princípios ativos já existentes paramelhorar a eficácia dos mesmos.Similarly the same can be done for elimination of toxic and fungicidal fungi at very low dosages. The compound and its derivatives, patent-pending object, can be mixed with existing active ingredients to improve their effectiveness.
O novo composto, objeto de pedido de patente, apresenta a vantagem deser menos agressivo ao meio ambiente, em razão da sua decomposição no sololevar a formação de subprodutos não tóxicos.The new compound, which is the subject of a patent application, has the advantage of being less aggressive to the environment, because of its decomposition in sololevar formation of non-toxic by-products.
Claims (9)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BRPI0804557A BRPI0804557B1 (en) | 2008-10-17 | 2008-10-17 | dimethylmercaptopyrimidylethane-derived organotin compound for fungicide formulation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BRPI0804557A BRPI0804557B1 (en) | 2008-10-17 | 2008-10-17 | dimethylmercaptopyrimidylethane-derived organotin compound for fungicide formulation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0804557A2 true BRPI0804557A2 (en) | 2010-07-20 |
| BRPI0804557B1 BRPI0804557B1 (en) | 2016-01-05 |
Family
ID=42335322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0804557A BRPI0804557B1 (en) | 2008-10-17 | 2008-10-17 | dimethylmercaptopyrimidylethane-derived organotin compound for fungicide formulation |
Country Status (1)
| Country | Link |
|---|---|
| BR (1) | BRPI0804557B1 (en) |
-
2008
- 2008-10-17 BR BRPI0804557A patent/BRPI0804557B1/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0804557B1 (en) | 2016-01-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B03A | Publication of an application: publication of a patent application or of a certificate of addition of invention | ||
| B15K | Others concerning applications: alteration of classification |
Free format text: AS CLASSIFICACOES ANTERIORES ERAM: C07D 239/38 , A01N 33/08 , A01N 43/40 , A01N 59/16 Ipc: A01N 55/04 (2006.01), A01N 33/10 (2006.01), C07D 2 |
|
| B09A | Decision: intention to grant | ||
| B16A | Patent or certificate of addition of invention granted |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 17/10/2008, OBSERVADAS AS CONDICOES LEGAIS. |