BR112019005145B1 - Moléculas com utilidade pesticida e seus intermediários - Google Patents
Moléculas com utilidade pesticida e seus intermediários Download PDFInfo
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- BR112019005145B1 BR112019005145B1 BR112019005145-7A BR112019005145A BR112019005145B1 BR 112019005145 B1 BR112019005145 B1 BR 112019005145B1 BR 112019005145 A BR112019005145 A BR 112019005145A BR 112019005145 B1 BR112019005145 B1 BR 112019005145B1
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- Prior art keywords
- alkyl
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- spp
- molecules
- methyl
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- 239000000543 intermediate Substances 0.000 title abstract description 36
- 239000000575 pesticide Substances 0.000 title description 56
- 241000607479 Yersinia pestis Species 0.000 abstract description 102
- 239000000203 mixture Substances 0.000 abstract description 79
- 238000000034 method Methods 0.000 abstract description 31
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- 241000244206 Nematoda Species 0.000 abstract description 14
- 230000000895 acaricidal effect Effects 0.000 abstract description 7
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- 241000425347 Phyla <beetle> Species 0.000 abstract description 5
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- 230000002013 molluscicidal effect Effects 0.000 abstract description 4
- 230000000361 pesticidal effect Effects 0.000 abstract description 3
- -1 butenyloxy Chemical group 0.000 description 321
- 150000001875 compounds Chemical class 0.000 description 71
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
- 239000002904 solvent Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 30
- 229910052739 hydrogen Inorganic materials 0.000 description 30
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
- 125000001424 substituent group Chemical group 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 238000009472 formulation Methods 0.000 description 25
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 125000003545 alkoxy group Chemical group 0.000 description 22
- 244000038559 crop plants Species 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 125000000217 alkyl group Chemical group 0.000 description 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 19
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 18
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 18
- 239000002585 base Substances 0.000 description 18
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- 241000894007 species Species 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
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- 229910052731 fluorine Inorganic materials 0.000 description 16
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- 239000000843 powder Substances 0.000 description 15
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- 239000011734 sodium Substances 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
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- 229910052763 palladium Inorganic materials 0.000 description 12
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- PMJRLYSMEOLBIU-UHFFFAOYSA-N methyl 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)quinoline-3-carboxylate Chemical group COC(=O)C1=CC2=CC=CC=C2N=C1C1=NC(C)(C(C)C)C(=O)N1 PMJRLYSMEOLBIU-UHFFFAOYSA-N 0.000 description 1
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 description 1
- SWSGRMHVZNTUEW-UHFFFAOYSA-N methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]propanoate Chemical compound C(C)(C)(C)OC(=O)NC(C(=O)OC)CC1=CC=C(C=C1)C1=NN(C=N1)C1=CC=C(C=C1)OC(F)(F)F SWSGRMHVZNTUEW-UHFFFAOYSA-N 0.000 description 1
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 description 1
- DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical group COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 description 1
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 description 1
- VGBNSONMEGTIDX-UHFFFAOYSA-N methyl 2-[(4-methylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC=CC(C)=N1 VGBNSONMEGTIDX-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- MDXGYOOITGBCBW-UHFFFAOYSA-N methyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 MDXGYOOITGBCBW-UHFFFAOYSA-N 0.000 description 1
- IAUMNRCGDHLAMJ-UHFFFAOYSA-N methyl 2-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 IAUMNRCGDHLAMJ-UHFFFAOYSA-N 0.000 description 1
- LYPWWQLKWQNQKV-UHFFFAOYSA-N methyl 2-[5-ethyl-2-[[4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(CC)=CC=C1COC1=CC=C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)C=C1 LYPWWQLKWQNQKV-UHFFFAOYSA-N 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
- FPEVHSIBUPWADM-UHFFFAOYSA-N methyl 2-[ethoxy-(propan-2-ylamino)phosphinothioyl]oxybenzoate Chemical group CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC FPEVHSIBUPWADM-UHFFFAOYSA-N 0.000 description 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
- DFYPVJHFCVSDEV-UHFFFAOYSA-N methyl 2-chloro-9h-fluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)C3=CC=CC=C3C2=C1 DFYPVJHFCVSDEV-UHFFFAOYSA-N 0.000 description 1
- HQTUEAOWLVWJLF-UHFFFAOYSA-N methyl 3,6-dichloropyridine-2-carboxylate Chemical group COC(=O)C1=NC(Cl)=CC=C1Cl HQTUEAOWLVWJLF-UHFFFAOYSA-N 0.000 description 1
- DTSSCQVCVYZGSI-UHFFFAOYSA-N methyl 3-amino-2,5-dichlorobenzoate Chemical group COC(=O)C1=CC(Cl)=CC(N)=C1Cl DTSSCQVCVYZGSI-UHFFFAOYSA-N 0.000 description 1
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 description 1
- AHGMXAFUHVRQAD-UHFFFAOYSA-N methyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 AHGMXAFUHVRQAD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Agronomy & Crop Science (AREA)
- Medicinal Chemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
a presente invenção refere-se ao campo de moléculas que têm utilidade pesticida contra pestes no filos nematoda, artropoda, e/ou molusca, processos para produzir tais moléculas e intermediários usados em tais processos, composições contendo tais moléculas, e processos de uso de tais moléculas contra tais pestes. estas moléculas podem ser usadas, por exemplo, como nematicidas, acaricidas, insecticidas, miticidas, e/ou moluscicidas. este documento descreve moléclas tendo a seguinte fórmula ("fórmula um" e "fórmula dois"). fórmula um, e fórmula dois
Description
[001] Este pedido reivindica o benefício de, e prioridades de Pedidos de Patente Provisório N° de Série US 62/437,323, depositado em 21 de dezembro de 2016, e US 62/464,429 depositado em 28 de fevereiro de 2017, cujos pedidos são aqui incorporados por referência em suas totalidades.
[002] Esta invenção se refere ao campo de moléculas tendo utilidade pesticida contra pestes em Filos Nematoda, Arthropoda, e Mollusca, processos para produzir tais moléculas e intermediários usados em tais processos, composições contendo tais moléculas, e processos de uso de tais moléculas contra tais pestes. Estas moléculas podem ser usadas, por exemplo, como nematicidas, acaricidas, inseticidas, miticidas e moluscidas.
[003] "A maioria das doenças humanas mais perigosas é transmitida por vetores de inseto" (Rivero, A. et al., Insect Control of Vector-Borne Diseases: When is Insect Resistance a Problem? Public Library of Science Pathogens, 6(8) (2010)). Historicamente, doenças transmitidas por vetor, tais como malaria, dengue, febre amarela, peste, e tifo transmitido por piolhos, entre outros, foram responsáveis por mais doenças humanas e mortes dos anos de 1600 ao inpicio dos anos de 1900 do que todas as causas combinadas (Gubler D., Resurgent Vector-Borne Diseases as a Global Health Problem, Emerging Infectious Diseases, Vol.4, No. 3, July-September (1998)). Atualmente, doenças transmitidas por vetor são responsáveis por cerca de 17% das doenças parasíticas e infecciosas globais. Estimou-se que cerca de 250 milhões de pessoas em torno do mundo têm malária e cerca de 800.000 morrem a cada ano - 85% daquelas mortes são crianças menores de cinco anos de idade. Mais de 250.000 a 500.000 casos de febre hemorrágica da dengue ocorrem a cada ano (Matthews, G., Integrated Vector Management: controlling vectors of malaria and other insect vector borne diseases (2011)). O controle de vetor desempenha um papel crítico na prevenção e controle de doenças infecciosas. Entretanto, resistência ao inseticida, incluindo resistência a múltiplos inseticidas, tem surgido em todas as espécies de inseto que são os principais vetores de doenças humanas (Rivero, A. et al.).
[004] A cada ano, insetos, patógenos de planta, e ervas daninhas destroem mais do que 40% de toda a produção potencial de alimentos. Esta perda ocorre apesar da aplicação de pesticidas e o uso de uma ampla gama de controles não químicos, tais como rotações de colheita e controles biológicos. Se apenas alguns destes alguns pudessem ser salvos, estes poderiam alimentar mais de três bilhões de pessoas no mundo que estão desnutridas (Pimental, D., Pest Control in World Agriculture, Agricultural Sciences - Vol. II (2009)).
[005] Nematodas parasíticos de planta estão entre as pestes mais disseminadas, e são frequentemente uma das mais indiciosas e caras. Estimou-se que perdas atribuíveis ao nematodas são de cerca de 9% nos países desenvolvidos a cerca de 15% em países não desenvolvidos. Entretanto, nos Estados Unidos da América, um levantamento de 35 Estados sobre várias colheitas indicou perdas derivadas de nematoda de até 25% (Nicol, J. et al., Current Nematode Threats to World Agriculture, Genomic and Molecular Genetics of Plant -Nematode Interactions (Eds. Jones, J. etal.), Capítulo 2, (2011)).
[006] Observa-se que os gastrópodes (lesmas e caracóis) são pestes de menor importância econômica do que insetos e nematodas, porém, em certas áreas, os gastropodes podem reduzir substancialmente produções, afetando severamente a qualidade dos produtos colhidos, bem como transmitindo doenças humanas, animais e de planta. Enquanto apenas algumas dezenas de espécies de gastrópodes são sérias pestes regionais, algumas espécies são pestes importantes em uma escala mundial. Em particular, gastrópodes afetam uma ampla variedade de colheitas agrícolas e hortículas, tais como colheitas aráveis, pastorais e de fibra; vegetais; legumes; mato e frutos de árvores; ervas e ornamentais (Speiser, B., Molluscicides, Enciclopedia of Pest Management (2002)).
[007] Cupins causam dano a todas as espécies de estruturas privadas e públicas, bem como aos recursos agrícolas e florestais. Em 2003, estimou-se que os cupins causem mais de US$20 bilhões em dano no mundo todo a cada ano (Su, N.Y., Overview of the global distribution and control of the Formosan subterranean termite, Sociobiology 2003, 41, 177-192).
[008] Portanto, por muitas razões, incluindo as razões acima, existe uma necessidade de novos pesticidas.
[009] Os exemplos fornecidos nas definições são geralmente não exaustivos e não devem ser construídos como limitante das moléculas descritas neste documento. Entende-se que um substituinte deve obedecer as regras de ligação química e restrições de compatibilidade estérica com relação à molécula particular à qual ela é ligada.
[0010] "Alquenila" significa um substituinte acíclico (pelo menos uma ligação dupla de carbono-carbono), ramificado ou não ramificado, que consiste em carbono e hidrogênio, por exemplo, vinila, alila, butenila, pentenila, e hexenila.
[0011] "Alquenilóxi" significa uma alquenila que também consiste em uma ligação simples de carbono-oxigênio, por exemplo, alilóxi, butenilóxi, pentenilóxi, hexenilóxi.
[0012] "Alcóxi" significa uma alquila que também consiste em uma ligação simples de carbono-oxigênio, por exemplo, metóxi, etóxi, propóxi, isopropóxi, butóxi, isobutóxi, e terc-butóxi.
[0013] "Alquila" significa um substituinte acíclico, saturado, ramificado ou não ramificado que consiste em carbono e hidrogênio, por exemplo, metila, etila, propila, isopropila, butila, e terc-butila.
[0014] "Alquinila" significa um substituinte acíclico, insaturado (pelo menos uma ligação tripla de carbono-carbono), ramificado ou não ramificado que consiste em carbono e hidrogênio, por exemplo, etinila, propargila, butinila, e pentinila.
[0015] "Alquinilóxi" significa uma alquinila que também consiste em uma ligação simples de carbono-oxigênio, por exemplo, pentinilóxi, hexinilóxi, heptinilóxi, e octinilóxi.
[0016] "Arila" significa um substituinte cíclico, aromático que consiste em hidrogênio e carbono, por exemplo, fenila, naftila, e bifenila.
[0017] "Cicloalquenila" significa um substituinte monocíclico ou policíclico, insaturado (pelo menos uma ligação dupla de carbono- carbono) que consiste em carbono e hidrogênio, por exemplo, ciclobutenila, ciclopentenila, ciclo-hexenila, norbornenila,biciclo[2.2.2]octenila, tetra-hidronaftila, hexa-hidronaftila, e octa- hidronaftila.
[0018] "Cicloalquenilóxi" significa uma cicloalquenila que também consiste em uma ligação simples de carbono-oxigênio, por exemplo, ciclobutenilóxi, ciclopentenilóxi, norbornenilóxi, e biciclo[2.2.2]octenilóxi.
[0019] "Cicloalquila" significa um substituinte monocíclico ou policíclico que consiste em carbono e hidrogênio, por exemplo, ciclopropila, ciclobutila, ciclopentila, norbornila, biciclo[2.2.2]octila, e deca-hidronaftila.
[0020] "Cicloalcóxi" significa uma cicloalquila que também consiste em uma ligação simples de carbono-oxigênio, por exemplo, ciclopropilóxi, ciclobutilóxi, ciclopentilóxi, norbornilóxi, e biciclo[2.2.2]octilóxi.
[0021] "Halo" significa flúor, cloro, bromo, e iodo.
[0022] "Haloalcóxi" significa um alcóxi que também consiste em, de um ao número máximo possível de, halos iguais ou diferentes, por exemplo, fluorometóxi, trifluorometóxi, 2,2-difluoropropóxi, clorometóxi, triclorometóxi, 1,1,2,2-tetrafluoroetóxi, e pentafluoroetóxi.
[0023] "Haloalquila" significa uma alquila que também consiste em, de um ao número máximo possível de, halos iguais ou diferentes, por exemplo, fluorometila, trifluorometila, 2,2-difluoropropila, clorometila, triclorometila, e 1,1,2,2-tetrafluoroetila.
[0024] "Heterociclila" significa um substituinte cíclico que pode ser totalmente saturado, parcialmente insaturado, ou totalmente insaturado, onde a estrutura cíclica contém pelo menos um carbono e pelo menos um heteroátomo, onde o referido heteroátomo é nitrogênio, enxofre, ou oxigênio. Exemplos de heterociclilas aromáticas incluem, porém nao estão limitados a, benzofuranila, benzoisothiazolila, benzoisoxazolila, benzoxazolila, benzothienila, benzothiazolila, cinnolinila, furanila, indazolila, indolila, imidazolila, isoindolila, isoquinolinila, isothiazolila, isoxazolila, oxadiazolila, oxazolinila, oxazolila, ftalazinila, pirazinila, pirazolinila, pirazolila, piridazinila, piridila, pirimidinila, pirrolila, quinazolinila, quinolinila, quinoxalinila, tetrazolila, tiazolinila, tiazolila, tienila, triazinila, e triazolila. Exemplos de heterociclilas totalmente saturadas incluem, porém não estão limitados à, piperazinila, piperidinila, morfolinila, pirrolidinila, tetra-hidrofuranila, e tetra- hidropiranila. Exemplos de heterociclilas parcialmente insaturadas incluem, porém não estão limitados à, 1,2,3,4-tetra-hidro-quinolinila, 4,5-di-hidro-oxazolila, 4,5-di-hidro-1H-pirazolila, 4,5-di-hidro-isoxazolila, e 2,3-di-hidro-[1,3,4]-oxadiazolila.
[0025] Este documento descreve as moléculas que têm a seguinte fórmula ("Fórmula Um" e/ou "Fórmula Dois")
[0026] em que:
[0027] (A) Ar1 é selecionado de
[0028] (1) furanila, fenila, piridazinila, piridila, pirimidinila, ou tienila, ou
[0029] (2) furanila substituída, fenila substituída, piridazinila substituída, piridila substituída, pirimidinila substituída, ou tienila substituída,
[0030] em que a referida furanila substituída, fenila substituída, piridazinila substituída, piridila substituída, pirimidinila substituída, ou tienila substituída, tem um ou mais substituintes independentemente selecionados de H, F, Cl, Br, I, CN, NO2, (C1-C8)alquila, (C1- C8)haloalquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2- C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, OSO2-(C1- C8)alquila, C(O)-NRxRy, (C1-C8)alquil-NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C3-C8)cicloalquila, C(O)O-(C3- C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2-C8)alquenila, (C1- C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil-S(O)n-(C1-C8)alquila, C(O)-(C1- C8)alquil-C(O)O-(C1-C8)alquila, fenila, e fenóxi,
[0031] em que cada substituinte de alquila, cicloalquila, alcóxi, alquenila, alquinila, fenila, e fenóxi pode ser opcionalmente substituídos com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, (C1-C8)alquila, (C1- C8)haloalquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2- C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1-C8)haloalquila, OSO2-(C1-C8)alquila, OSO2-(C1-C8)haloalquila, C(O)- NRxRy, (C1-C8)alquil-NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C1-C8)haloalquila, C(O)O-(C1-C8)haloalquila, C(O)-(C3- C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila,C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil- S(O)n-(C1-C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1-C8)alquila, fenila, e fenóxi;
[0032] (B) Het é um anel heterocíclico saturado ou insaturado de 5 ou 6 membros, contendo um ou mais heteroátomos independentemente selecionados de nitrogênio, enxofre ou oxigênio, e onde Ar1 e Ar2 não estão orto uns para os outros (podem estar meta ou para, tal como, para um anel de cinco membros eles são 1,3 e para um anel de 6 membros são ou 1,3 ou 1,4) e onde o referido anel heterocíclico pode também ser substituído com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, oxo, (C1-C8)alquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C2-C8)alquenila, (C2- C8)alquinila, S(O)n-(C1-C8)alquila, OSO2-(C1-C8)alquila, C(O)-NRxRy, (C1-C8)alquil-NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)- (C3-C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil- S(O)n-(C1-C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1-C8)alquila, fenila, e fenóxi,
[0033] em que cada substituinte de alquila, cicloalquila, alcóxi, alquenila, alquinila, fenila, e fenóxi pode ser opcionalmente substituído com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, (C1-C8)alquila, (C1- C8)haloalquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2- C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1- C8)haloalquila, OSO2-(C1-C8)alquila, OSO2-(C1-C8)haloalquila, C(O)- NRxRy, (C1-C8)alquil-NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C1-C8)haloalquila, C(O)O-(C1-C8)haloalquila, C(O)-(C3- C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil- S(O)n-(C1-C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1-C8)alquila, fenila, e fenóxi;
[0034] (C) Ar2 é selecionado de
[0035] (1) furanila, fenila, piridazinila, piridila, pirimidinila, ou tienila,ou
[0036] (2) furanila substituída, fenila substituída, piridazinila substituída, piridila substituída, pirimidinila substituída, ou tienila substituída, e onde Het e L não estão orto uns para os outros (podem estar meta ou para, tal como, para um anel de cinco membros eles são 1,3 e para um anel de 6 membros são ou 1,3 ou 1,4);
[0037] em que a referida furanila substituída, fenila substituída, piridazinila substituída, piridila substituída, pirimidinila substituída, ou tienila substituída, tem um ou mais substituintes independentemente selecionados de H, F, Cl, Br, I, CN, NO2, NRxRy, (C1-C8)alquila, (C1- C8)haloalquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2- C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, OSO2-(C1- C8)alquila, C(O)-NRxRy, (C1-C8)alquil-NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C3-C8)cicloalquila, C(O)O-(C3- C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2-C8)alquenila, (C1- C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil-S(O)n-(C1-C8)alquila, C(O)-(C1- C8)alquil-C(O)O-(C1-C8)alquila, fenila, e fenóxi,
[0038] em que cada substituinte de alquila, haloalquila, cicloalquila, alcóxi, haloalcóxi, alquenila, alquinila, fenila, e fenóxi pode ser opcionalmente substituído com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, (C1-C8)alquila, (C1-C8)haloalquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2-C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1-C8)haloalquila, OSO2-(C1-C8)alquila, OSO2-(C1-C8)haloalquila, C(O)-NRxRy, (C1-C8)alquil-NRxRy, C(O)-(C1- C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C1-C8)haloalquila, C(O)O-(C1- C8)haloalquila, C(O)-(C3-C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1- C8)alquila, (C1-C8)alquil-S(O)n-(C1-C8)alquila, C(O)-(C1-C8)alquil-C(O)O- (C1-C8)alquila, fenila, e fenóxi;
[0039] (D) L é ligador selecionado de
[0040] (1) um ligador de (C1-C4)hidrocarbila saturado, ou insaturado,linear substituído, e
[0041] (2) um ligador de (C3-C8)hidrocarbila saturado ou insaturado, cíclico substituído,
[0042] em que cada um dos referidos ligadores conecta Ar2 a NY e
[0043] em que o referido ligador de (C1-C4)hidrocarbila linear substituído e ligador de (C3-C8)hidrocarbila cíclico substituído tem um ou mais substituintes independentemente selecionados de R8, R9, R10, R11, e R12, em que cada R8, R9, R10, R11, e R12, é selecionado de -NRAC(O)-RB, -NRAC(O)O-RB, -C(O)-OH, ou -C(O)O-RB,
[0044] onde RA é H ou (C1-C8)alquila, e RB é (C1-C8)alquila ou (C1- C8)alquila substituída com pelo menos uma fenila;
[0045] (E) R1 é selecionado do grupo que consiste em H, (C1-C8)alquila, (C3-C8)cicloalquila, (C2-C8)alquenila, (C2-C8)alquinila, S(O)n- (C1-C8)alquila, C(O)-NRxRy, (C1-C8)alquil-NRxRy, C(O)O-(C1-C8)alquila, C(O)-(C3-C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2- C8)alquenila, C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil-OC(O)-(C1-C8)alquila, (C1-C8)alquil-S(O)n-(C1-C8)alquila, (C1-C8)alquil-OC(O)O-(C1-C8)alquila, (C1-C8)alquil-C(O)O-(C1- C8)alquila, C(O)alquila, (C1-C8)alquil-C(O)-(C1-C8)alquila, (C1- C8)alquilfenila, (C1-C8)alquil-O-fenila,
[0046] em que cada alquila, cicloalquila, alquenila, e alquinila pode ser opcionalmente substituída com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, oxo, (C1-C8)alquila, (C1-C8)haloalquila, (C3- C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2-C8)alquenila, (C2- C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1-C8)haloalquila, OSO2-(C1- C8)alquila, OSO2-(C1-C8)haloalquila, C(O)-NRxRy, (C1-C8)alquil-NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C1-C8)haloalquila, C(O)O-(C1-C8)haloalquila, C(O)-(C3-C8)cicloalquila, C(O)O-(C3- C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2-C8)alquenila, (C1- C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil-S(O)n-(C1-C8)alquila, C(O)-(C1- C8)alquil-C(O)O-(C1-C8)alquila, fenila, e fenóxi;
[0047] (F) Q e Q1 são cada quais independentemente selecionados do grupo que consiste em O e S;
[0048] (G) R2 é selecionado do grupo que consiste em (J), H, (C1-C8)alquila, (C3-C8)cicloalquila, (C2-C8)alquenila, (C2-C8)alquinila, C(O)- (C1-C8)alquila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil-S(O)n-(C1- C8)alquila, (C1-C8)alquilfenila, (C1-C8)alquil-O-fenila, C(O)-(Het-1), (Het- 1), (C1-C8)alquil-(Het-1), (C1-C8)alquil-OC(O)-(C1-C8)alquila, (C1- C8)alquil-OC(O)O-(C1-C8)alquila, (C1-C8)alquil-OC(O)-NRxRy, (C1- C8)alquil-C(O)-N(Rx)(C1-C8)alquil-(Het-1), (C1-C8)alquil-C(O)-(Het-1), (C1-C8)alquil-C(O)-N(Rx)(C1-C8)alquil(NRxRy)-C(O)OH, (C1-C8)alquil- C(O)-N(Rx)(C1-C8)alquil-NRxRy, (C1-C8)alquil-C(O)-N(Rx)(C1-C8)alquil- N(Rx)-C(O)O-(C1-C8)alquila, (C1-C8)alquil-C(O)-N(Rx)(C1- C8)alquil(N(Rx)-C(O)O-(C1-C8)alquil)-C(O)OH, (C1-C8)alquil-C(O)-(Het- 1)-C(O)O-(C1-C8)alquila, (C1-C8)alquil-OC(O)O-(C1-C8)alquila, (C1- C8)alquil-OC(O)-(C1-C8)alquila, (C1-C8)alquil-OC(O)-(C3-C8)cicloalquila, (C1-C8)alquil-OC(O)-(Het-1), (C1-C8)alquil-OC(O)-(C1-C8)alquil-N(Rx)- C(O)O-(C1-C8)alquila, (C1-C8)alquil-NRxRy, (C1-C8)alquil-S(O)n-(Het-1), e (C1-C8)alquil-O-(Het-1),
[0049] em que cada alquila, cicloalquila, alquenila, alquinila, fenila, e (Het-1) pode ser opcionalmente substituída com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, NRxRy, (C1-C8)alquila, (C1-C8)haloalquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C2-C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1-C8)haloalquila, OSO2-(C1-C8)alquila, OSO2-(C1-C8)haloalquila, C(O)H, C(O)OH, C(O)-NRxRy, (C1-C8)alquil- NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C1- C8)haloalquila, C(O)O-(C1-C8)haloalquila, C(O)-(C3-C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2- C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil-S(O)n-(C1- C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1-C8)alquil), fenila, fenóxi, Si((C1-C8)alquil)3, S(O)n-NRxRy, e (Het-1);
[0050] (H) R3 é selecionado do grupo que consiste em (C3- C8)cicloalquila, fenila, (C1-C8)alquilfenila, (C1-C8)alquil-O-fenila, (C2- C8)alquenil-O-fenila, (Het-1), (C1-C8)alquil-(Het-1), e (C1-C8)alquil-O- (Het-1),
[0051] em que cada alquila, cicloalquila, alquenila, fenila, e (Het-1) pode ser opcionalmente substituída com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, NRxRy, (C1-C8)alquila, (C1-C8)haloalquila, (C3- C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2-C8)alquenila, (C2- C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1-C8)haloalquila, OSO2-(C1- C8)alquila, OSO2-(C1-C8)haloalquila, C(O)H, C(O)-NRxRy, (C1-C8)alquil- NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C1- C8)haloalquila, C(O)O-(C1-C8)haloalquila, C(O)-(C3-C8)cicloalquila, C(O)O-(C1-C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2- C8)alquenila, O-(C1-C8)alquila, S-(C1-C8)alquila, (C1-C8)alquil-O-(C1- C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1-C8)alquila, fenila, fenóxi, e (Het-1),
[0052] (I) R4 é selecionado do grupo que consiste em (J), H, (C1- C8)alquila, (C3-C8)cicloalquila, (C2-C8)alquenila, (C2-C8)alquinila, C(O)- (C1-C8)alquila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil-S(O)n-(C1- C8)alquila, (C1-C8)alquilfenila, (C1-C8)alquil-O-fenila, C(O)-(Het-1), (Het- 1), (C1-C8)alquil-(Het-1), (C1-C8)alquil-OC(O)-(C1-C8)alquila, (C1- C8)alquil-OC(O)O-(C1-C8)alquila, (C1-C8)alquil-OC(O)-NRxRy, (C1- C8)alquil-C(O)-N(Rx)(C1-C8)alquil-(Het-1), (C1-C8)alquil-C(O)-(Het-1), (C1-C8)alquil-C(O)-N(Rx)(C1-C8)alquil(NRxRy)-C(O)OH, (C1-C8)alquil- C(O)-N(Rx)(C1-C8)alquil-NRxRy, (C1-C8)alquil-C(O)-N(Rx)(C1-C8)alquil- N(Rx)-C(O)O-(C1-C8)alquila, (C1-C8)alquil-C(O)-N(Rx)(C1- C8)alquil(N(Rx)-C(O)O-(C1-C8)alquil)-C(O)OH, (C1-C8)alquil-C(O)-(Het- 1)-C(O)O-(C1-C8)alquila, (C1-C8)alquil-OC(O)O-(C1-C8)alquila, (C1- C8)alquil-OC(O)-(C1-C8)alquila, (C1-C8)alquil-OC(O)-(C3-C8)cicloalquila, (C1-C8)alquil-OC(O)-(Het-1), (C1-C8)alquil-OC(O)-(C1-C8)alquil-N(Rx)- C(O)O-(C1-C8)alquila, (C1-C8)alquil-NRxRy, (C1-C8)alquil-S(O)n-(Het-1), e (C1-C8)alquil-O-(Het-1),
[0053] em que cada alquila, cicloalquila, alquenila, alquinila, fenila, e (Het-1) pode ser opcionalmente substituído com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, NRxRy, (C1-C8)alquila, (C1-C8)haloalquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C2-C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1-C8)haloalquila, OSO2-(C1-C8)alquila, OSO2-(C1-C8)haloalquila, C(O)H, C(O)OH, C(O)-NRxRy, (C1-C8)alquil- NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C1- C8)haloalquila, C(O)O-(C1-C8)haloalquila, C(O)-(C3-C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2- C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil-S(O)n-(C1- C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1-C8)alquila, fenila, fenóxi, Si((C1-C8)alquil)3, S(O)n-NRxRy, e (Het-1);
[0054] (J) R2 e R4 juntamente com CX(Q1)(NX), podem formar um anel heterociclico, saturado ou insaturado de 4 a 7 membros, que pode também conter um ou mais heteroátomos selecionados do grupo que consiste em nitrogênio, enxofre e oxigênio,
[0055] em que cada anel heterocíclico pode ser opcionalmente substituído com um ou mais substituintes independentemente selecionados do grupo que consiste em R5, R6, e R7,
[0056] em que R5, R6, e R7 são cada quais independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, OH, NO2, NRxRy, oxo, tioxo, (C1-C8)alquila, (C1-C8)haloalquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2-C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1-C8)haloalquila, OSO2-(C1-C8)alquila, OSO2-(C1-C8)haloalquila, C(O)H, C(O)-(C1-C8)alquila, C(O)O-(C1- C8)alquila, C(O)-(C1-C8)haloalquila, C(O)O-(C1-C8)haloalquila, C(O)-(C3- C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil- S(O)n-(C1-C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1-C8)alquila, fenila, e (Het-1);
[0057] (K) Rx e Ry são cada quais independentemente selecionados do grupo que consiste em H, (C1-C8)alquila, (C3-C8)cicloalquila, (C1- C8)alcóxi, (C2-C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, OSO2-(C1-C8)alquila, C(O)H, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, , C(O)-(C3-C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2- C8)alquenila, C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil-S(O)n-(C1-C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1- C8)alquila, fenila, e (C1-C8)alquilfenila,
[0058] em que cada alquila, cicloalquila, alcóxi, alquenila, alquinila, fenila, e alquilfenila pode ser opcionalmente substituído com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, (C1-C8)alquila, (C1-C8)haloalquila, (C3- C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2-C8)alquenila, (C2- C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1-C8)haloalquila, OSO2-(C1- C8)alquila, OSO2-(C1-C8)haloalquila, C(O)H, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C1-C8)haloalquila, C(O)O-(C1- C8)haloalquila, C(O)-(C3-C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1- C8)alquila, (C1-C8)alquil-S(O)n-(C1-C8)alquila, C(O)-(C1-C8)alquil-C(O)O- (C1-C8)alquila, fenila, e (Het-1);
[0059] (L) (Het-1) é um anel heterocíclico saturado ou insaturado de 5 ou 6 membros, contendo um ou mais heteroátomos independentemente selecionados de nitrogênio, enxofre ou oxigênio,
[0060] em que o referido anel heterocíclico pode ser opcionalmente substituído com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, oxo, (C1-C8)alquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C2-C8)alquenila, (C2- C8)alquinila, S(O)n-(C1-C8)alquila, OSO2-(C1-C8)alquila, C(O)-NRxRy, (C1-C8)alquil-NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)- (C3-C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila, C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil- S(O)n-(C1-C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1-C8)alquila, fenila, e fenóxi,
[0061] em que cada substituinte de alquila, cicloalquila, alcóxi, alquenila, alquinila, fenila, e fenóxi pode ser opcionalmente substituído com um ou mais substituintes independentemente selecionados do grupo que consiste em H, F, Cl, Br, I, CN, NO2, (C1-C8)alquila, (C1- C8)haloalquila, (C3-C8)cicloalquila, (C1-C8)alcóxi, (C1-C8)haloalcóxi, (C2- C8)alquenila, (C2-C8)alquinila, S(O)n-(C1-C8)alquila, S(O)n-(C1- C8)haloalquila, OSO2-(C1-C8)alquila, OSO2-(C1-C8)haloalquila, C(O)- NRxRy, (C1-C8)alquil-NRxRy, C(O)-(C1-C8)alquila, C(O)O-(C1-C8)alquila, C(O)-(C1-C8)haloalquila, C(O)O-(C1-C8)haloalquila, C(O)-(C3- C8)cicloalquila, C(O)O-(C3-C8)cicloalquila, C(O)-(C2-C8)alquenila,C(O)O-(C2-C8)alquenila, (C1-C8)alquil-O-(C1-C8)alquila, (C1-C8)alquil- S(O)n-(C1-C8)alquila, C(O)-(C1-C8)alquil-C(O)O-(C1-C8)alquila, fenila, e fenóxi;
[0062] (M) n é cada qual individualmente 0, 1, ou 2; e
[0063] N-óxidos, sais de adição de ácido agricolamente aceitáveis, derivados de sal, solvatos, derivados de éster, polimorfos cristalinos, isótopos, estereoisômeros resolvidos, e/ou tautômeros.
[0064] Para evitar dúvidas, as designações de NX e NY se referem aos átomos de nitrogênio ordinários nas localizações específicas como mostrado na Fórmula Um e Fórmula Dois. Similarmente, a designação de CX se refere a um átomo de carbon ordinário na localização específica como mostrado na Fórmula Um e Fórmula Dois.
[0065] Em uma modalidade, Ar1 é uma fenila não substituída. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Het, Ar2, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0066] Em outra modalidade, Ar1 é uma fenila substituída que tem um ou mais substituintes selecionados de C1-C6 haloalquila e C1-C6 haloalcóxi. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de ligações de hidrocarbila de Het, Ar2, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0067] Em outra modalidade, Ar1 é uma fenila substituída que tem um ou mais substituintes selecionados de CF3, OCF3, e OC2F5. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Het, Ar2, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0068] Em outra modalidade, Het é selecionado de benzofuranila, benzoisotiazolila, benzoisoxazolila, benzoxazolila, benzotienila, benzotiazolila, cinnolinila, furanila, indazolila, indolila, imidazolila, isoindolila, isoquinolinila, isotiazolila, isoxazolila, oxadiazolila, oxazolinila, oxazolila, ftalazinila, pirazinila, pirazolinila, pirazolila, piridazinila, piridila, pirimidinila, pirrolila, quinazolinila, quinolinila, quinoxalinila, tetrazolila, tiazolinila, tiazolila, tienila, triazinila, triazolila, piperazinila, piperidinila, morfolinila, pirrolidinila, tetra-hidrofuranila, tetra-hidropiranila, 1,2,3,4-tetra-hidro-quinolinila, 4,5-di-hidro-oxazolila, 4,5-di-hidro-1H-pirazolila, 4,5-di-hidro-isoxazolila, e 2,3-di-hidro-[1,3,4]- oxadiazolila.
[0069] Em outra modalidade, Het é triazolila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Ar2, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0070] Em outra modalidade, Het é 1,2,4-triazolila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Ar2, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0071] Em outra modalidade, Het é oxadiazolila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Ar2, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0072] Em outra modalidade, Het é 1,3,4-oxadiazolila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Ar2, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0073] Em outra modalidade, Het é pirazolila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Ar2, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0074] Em outra modalidade, Ar2 é fenila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0075] Em outra modalidade, Ar2 é uma fenila não substituída. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0076] Em outra modalidade, Ar2 é uma fenila substituída que tem um ou mais substituintes selecionados de C1-C6 alquil. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0077] Em outra modalidade, Ar2 é uma fenila substituída que tem um ou mais substituintes em que o referido substituinte é CH3. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, R1, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0078] Em outra modalidade, R1 é H. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R2, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0079] Em outra modalidade, R2 é (J), H, (C1-C6)alquila, (C1-C6)alquil-O-C(O)-(C1-C6)alquila, (C1-C6)alquil-O-C(O)-N(RxRy), ou (C1C6 alquil)-S-(Het-1). Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R1, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0080] Em outra modalidade, R2 é (J), H, CH3, (C1-C6)alquila, CH2OC(O)CH(CH3)2, CH2OC(O)N(H)(C(O)OCH2Ph), ou CH2S(3,4,5- trimetóxi-2-tetra-hidropiran). Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R1, R3, R4, Q, Q1, R2 e R4, e/ou L.
[0081] Em outra modalidade, R3 é fenila substituída. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R1, R2, R4, Q, Q1, R2 e R4, e/ou L.
[0082] Em outra modalidade, R3 é fenila substituída, em que a referida fenila substituída tem um ou mais substituintes selecionados de F, Cl, (C1-C6)alquila, (C3-C6)cicloalquila, (C1-C6)alcóxi, e fenila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R1, R2, R4, Q, Q1, R2e R4, e/ou L.
[0083] Em outra modalidade, R3 é fenila substituída, em que a referida fenila substituída tem um ou mais substituintes selecionados de F, CH3, 2-CH(CH3)2, CH(CH3)(C2H5), OCH3, e fenila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R1, R2, R4, Q, Q1, R2e R4, e/ou L.
[0084] Em outra modalidade, R3 é fenila substituída, em que a referida fenila substituída tem mais do que um substituinte e pelo menos um par dos referidos substituintes não estão orto uns para os outros. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R1, R2, R4, Q, Q1, R2 e R4, e/ou L.
[0085] Em outra modalidade, R3 é (C1-C6)alquilphenila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R1, R2, R4, Q, Q1, R2e R4, e/ou L.
[0086] Em outra modalidade, R3 é (Het-1). Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R1, R2, R4, Q, Q1, R2e R4, e/ou L.
[0087] Em outra modalidade, R4 é H. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila de Ar1, Het, Ar2, R1, R2, R3, Q, Q1, R2 e R4, e/ou L.
[0088] Em outra modalidade, Q é O. Esta modalidade pode ser usada em combinação com outras modalidades de hidrocarbila de Ar1, Het, Ar2, Q1, R1, R2, R3, R4, R2 e R4, e/ou L
[0089] Em outra modalidade, Q1 é O. Esta modalidade pode ser usada em combinação com outras modalidades de hidrocarbila de Ar1, Het, Ar2, Q, R1, R2, R3, R4, R2 e R4, e/ou L.
[0090] Em outra modalidade, R2 e R4 são uma ligação de hidrocarbila, em que a referida ligação de hidrocarbila com oxo ou (C1- C6)alquila. Esta modalidade pode ser usada em combinação com outras modalidades de Ar1, Het, Ar2, R1, R2, R3, R4, Q, Q1, e/ou L.
[0091] Em outra modalidade, R2 e R4 são uma ligação de hidrocarbila, em que a referida ligação de hidrocarbila é CH2C(O), C(C(OH)(CH3)2)C(O), C(ciclopropil)C(O), C(CH3)2C(O), CFHC(O), CBrHC(O), CH(CH3)C(O), CH2CH2, CH2C(OH)(CH3), CH2CH2CH2, CH2CH2C(O), CH2CH(CH3)CH2, N(CH3)C(O), N(CH2CH3)C(O),CH=C(CH3), ou CH2CH(CH3). Esta modalidade pode ser usada em combinação com outras modalidades de Ar1, Het, Ar2, R1, R2, R3, R4, Q, Q1, e/ou L.
[0092] Em outra modalidade, L é CH2, CH2CH2, CH2CH(CH3), CH2C(CH3)2, CH2CH(CH2CH3), CH=CH, CH(CH3)CH2, C(CH3)2CH2, CHBrCH2, CH2C(ciclopropil), CH(CH2CH3)CH2, C(CH3)=CH, CH2CH2CH2, CH(CH3)CH(CH3), CH2CH2CH2CH2, CHCCH2CH2,ciclopropila, ou ciclo-hexila. Esta modalidade pode ser usada em combinação com outras modalidades de ligações de hidrocarbila Ar1, Het, Ar2, R1, R2, R3, R4, Q, Q1, e/ou R2 e R4.
[0093] A maioria das moléculas de Fórmula Um e Fórmula Dois pode ser descrita em duas ou mais formas tautoméricas tais como quando R1, R2, ou R4 é H. Quaisquer e todos os tautômeros alternativos são incluídos dentro do escopo desta Fórmula Um e this Fórmula Dois, e nenhuma inferência deve ser feita como se a molécula existisse como a forma tautomérica da qual ela é extraída.
[0094] Moléculas de Fórmula Um e Fórmula Dois podem ser preparadas preparando um intermediário de trialila, Ar1-Het-Ar2, e em seguida ligando-o a um intermediário apropriado para formar um composto desejado. Uma ampla variedade de intermediários de triarila pode ser usada para preparar moléculas de Fórmula Um e Fórmula Dois, contanto que tais intermediários de triarila contenha um grupo funcional adequado em Ar2 ao qual o restante do grupo funcional desejado pode ser ligado. Grupos funcionais adequados incluem um amino, isocianato, carboxila, ou um halogênio (preferivalmente, bromo ou iodo). Estes intermediários de triarila podem ser preparados pelos métodos anteriormente descritos na literatura química, incluindo Crouse, et al., WO2009102736 (a descrição completa da qual é pelo presente incorporado por referência).
[0095] Os aldeídos de triarila usados como precursores na preparação das moléculas de Fórmula Um e Fórmula Dois podem ser preparados de acordo com os procedimentos descritos em Crouse, et al., US 2012/0202688 A1. Alguns dos procedimentos descritos requerem o uso de intermediários halo-arila, Ar1-Het-Ph-Br, que são novos intermediários. Estes podem ser preparados como descrito no Esquema 1 abaixo. 3-(4-Bromofenil)-1,2,4-triazol (1-2) é preparado em duas etapas de 4-bromobenzamida (1-1) sob condições anteriormente descritas (etapa a, Crouse, et al., WO2009102736). Este triazol pode em seguida ser acoplado a um haleto 1-3 (R = (C1-C6)haloalcóxi) tal como bromobenzeno de 4-trifluorometoxifenila, na presença de carbonato de césio ou fosfato de potássio, em um solvente polar, aprótico tal como N,N-dimetilformamida. Esta reação é catalisada por um sal de cobre tal como iodeto de cobre(I) e um quelante tal como 8- hidroxiquinolina, ambos presentes em cerca de 0,05 a cerca de 0,25 equivalentes, em uma temperatura variando entre cerca de 80 °C e cerca de 140 °C, para formar o 1-aril-3-(4-bromofenil)triazol 1-4 (etapa b)Esquema 1
[0096] Moléculas de Fórmula Um e Fórmula Dois, em que L é um ligador de um carbono, podem ser preparadas de intermediários de ácido ou amina descritos no Esquema 2 e Esquema 3, respectivamente. Precursores de ácido 2-5 (Ar1-Het-Ar2-L-CO2H), não substituídos ou mono- ou dissubstituídos com R8; podem ser preparados como mostrado no Esquema 2. Ésteres borônicos 2-2 (etapa a) podem ser preparados usando condições Miyaura de halofenil ésteres 2-1. O acoplamento de ésteres de boronato com um bromo-heterociclo 2-3 (etapa b) pode ser realizado usando um catalisador de paládio e ligante de fosfina, na presença de uma base, tal como bicarbonato de sódio, fosfato de potássio, ou fluoreto de césio, em um sistema de solvente adequado, tal como dioxano/água, em temperaturas de cerca de 50 °C a cerca de 120 °C para formar intermediários de triaril éster 2-4. Entre os catalisadores de paládio, tetracis(trifenilfosfina)paládio(0) é preferido, embora outros catalisadores de paládio bem conhecidos possam ser usados. Saponificação do éster pode ser obtida usando uma base forte tal como hidróxido de sódio ou hidróxido de lítio em metanol ou etanol com ou sem tetra-hidrofurano/água para fornecer o ácido carboxílico desejado 2-5 (etapa c). Esquema 2
[0097] Precursores de substituídos ou mono- ou preparados como mostrado podem ser protegidas usando cloroformiato de benzila na presença de uma base tal como trietilamina em um solvente aprótico tal como diclorometano a cerca de -10 °C a cerca de 10 °C para fornecer benzil aminas protegidas por N-carboxibenzila (Cbz) 3-2 (etapa a).Alternativamente, outros grupos de proteção de N tais como terc- butoxicarbonila (BOC) ou 9-fluorenilmetiloxicarbonila (Fmoc) podem ser empregados na etapa a usando condições similares descritas acima para Cbz. O éster borônico protegido por Cbz 3-3 pode ser preparado usando condições Miyaura (etapa b). O acoplamento dos ésteres de boronato com um bromo-heterociclo 2-3 pode ser realizado usando um catalisador de paládio e ligante de fosfina, na presença de uma base, tal como bicarbonato de sódio, fosfato de potássio, ou fluoreto de césio, em um sistema de solvente adequado, tal como dioxano/água, em temperaturas de cerca de 50 °C a cerca de 120 °C para formar intermediários de aminoalquilfenila protegidos por N 3-4 (etapa c). A remoção do grupo Cbz pode ser realizada sob condições acídicas com um ácido forte tal como brometo de hidrogênio, seguido por neutralização com uma base tal como bicarbonato de sódio ou hidróxido de sódio, para fornecer os precursores de amina livre 3-5 (Ar1-Het-Ar2- L-NH2, etapa d). Métodos similares poderiam ser aplicados ao compostos, em que L é maior do que 1 átomo de carbono.Esquema 3
[0098] Preparação de compostos, em que L é um grupo de dois átomos é descrita nos Esquemas 4 a Esquemas 6. A condensação do aldeído 4-1 (R9 = H) (descrito em US 2012/0202688 A1) com reagentes tais como dietilfosfonoacetato de etila ou um reagente de Wittig tal como 2-(trifenilfosforanilideno)propanoato) de etila ou acetatos α-substituidos tais como 2-fluoroacetato de etila ou 2-cianoacetato de etila na presença de uma base adequada tal como hidreto de sódio ou n-butil lítio em solventes apróticos tais como tetra-hidrofurano ou dietil éter em temperaturas de cerca de -78 °C a cerca de 20 °C podem ser usados para preparar ésteres acrílicos 4-2 (etapa a) não substituídos ou mono- substituídos com R9 e/ou R10. Saponificação d éster resultante pode ser obtida usando uma base forte tal como hidróxido de sódio em metanol ou etanol com ou sem tetra-hidrofuran/água para fornecer o ácido carboxílico de vinila 4-3 (etapa b). Em alguns casos, a condensação parcial de aldeído 4-1 (R9 = H) pode resultar no isolamento do intermediário de álcool 4-4 (etapa c) especialmente quando R10 é retirado de elétrons. A substituição deste álcool com reagentes nucleofílicos tal como Deoxo-Fluor® (etapa d) seguida por saponificação como acima descrito (etapa e) pode gerar ácido carboxílicos de etila altamente substituídos 4-5 adicionalmente substituídos com R11, em que R11 é definido como R8 acima. Quando a ligação saturada é preferida, o éster acrílico 4-2 pode ser convertido no ciclopropano correspondente 4-6 não substituído ou mono- ou dissubstituído com R12; com iletos de enxofre tais como aqueles formados in situ de iodeto de trimetilsulfônio na presença de uma base inorgânica tal como hidreto de sódio em um solvente aprótico polar tal como sulfóxido de dimetila ou tetraidrofurano (etapa f). Igualmente, o éster acrílico 4-2 pode ser reduzido ao alcano origem 4-8 usando gás de hidrogênio e um catalisador de paládio (etapa h). Tanto o ciclopropano quanto os ésteres de alcano podem ser saponificados sob as condições básicas descritas acima para gerar os ácidos carboxílicos livres 4-7 (etapa g) e 4-9 (etapa i), respectivamente.
[0099] De uma maneira similar, a condensação da cetona 4-1 (R9 = alquila) (descrita no WO 2011017504 A1) com dietilfosfonoacetato de etila ou um reagente de Wittig tal como 2-(trifenilfosforanilide no)propanoato de etila ou ésteres de alquila α-substituidos tal como 2- fluoroacetato de etila ou 2-cianoacetato de etila sob condições similares descritas acima pode fornecer os ésteres acrílicos de α-alquila 4-2 ou álcoois 4-4. O tratamento subsequente de 4-2 ou 4-4 como descrito acima para R9 = H pode levar a ácidos carboxílicos insaturados (4-3) ou saturados (4-5, 4-7, 4-9) correspondentes.Esquema 4
[00100] Alternativamente, os compostos em que L é um ligador de dois carbonos podem também ser preparados como mostrado no Esquema 5. Usando as condições, primeiramente, descritas por Molander et al. Org. Lett. 2007, 9, páginas 203 a 206, o acoplamento de um brometo 5-1 (Ar1-Het-Ar2-Br, etapa a), com (2-((terc-butoxicarbonil)amino)etil)trifluoroborato de potássio na presença de um catalisador de paládio tal como acetato de paládio(II), e uma base tal como carbonato de césio, em temperaturas de cerca de 80 °C a cerca de 120 °C, resulta na formação do derivado de 2-(terc- butoxicarbonil)amino)etila correspondente 5-2. Além disso, o tratamento deste material com de cerca de 1 a cerca de 5 equivalentes de um ácido tal como ácido trifluoroacético (TFA) ou cloreto de hidrogênio, em um solvente aprótico tal como diclorometano ou dioxano em temperaturas de cerca de 0 °C a cerca de 50 °C, resulta na clivagem do grupo de terc- butoxicarbonila e formação do sal da amina 5-3 (Ar1-Het-Ar2-L-NH3+A-, em que A- é CF3CO2- ou Cl-, etapa b).Esquema 5
[00101] Os precursores de aminoalquila 6-5 (Ar1-Het-Ar2-L-NH2), em que L é átomos de dois carbono, mono- ou dissubstituídos com R9, em que R9 é definido como acima; e não substituídos ou mono-substituídos com R10, em que R10 é definido como acima, podem ser preparados como mostrado no Esquema 6. Os carbinóis de halofenila não substituídos 6-1 (R9 e R10 são H), em que X pode ser selecionado de Cl, Br, ou I, são comercialmente disponíveis. Os carbinóis 6-1 que são mono- ou dissubstituídos em R9 podem ser preparados do acetato de halofenila correspondente 6-I (etapa a) em modelo similar àquele descrito por Shin et al. Bioorg. Med. Chem. Lett. 2008, 18, páginas 4424 a 4427 seguido por redução com hidreto de metal tal como hidreto de alumínio de lítio em um solvente etéreo tal como tetraidrofurano ou éter dietílico em temperaturas em ou abaixo de cerca de 0 °C. Ambos 6-I e 6-II podem ser também mono-substituídos (etapa b ou etapa c) com R10 por meio de redução ao aldeído correspondente com hidreto de metal tal como hidreto de di-isobutilalumínio e, além disso, o tratamento com um reagente de Grignard em um modelo similar àquele descrito por Brimble et al. Org. Lett. 2012, 14, páginas 5820 a 5823. Os carbinóis 6-1 podem ser tratados com ftalimida sob condições de Mitsunobu para gerar intermediários de N-ftalimido 6-2 (etapa d). O haleto pode ser convertido em um éster borônico sob condições Miyaura para formar ésteres de boronato 6-3 (etapa e). O acoplamento dos ésteres de boronato com um bromo-heterociclo 2-3 pode ser realizado usando um catalisador de paládio, tal como tetracis(trifenilfosfina)paládio(0), na presença de uma base, tal como bicarbonato de sódio, em um sistema de solvente adequado, tal como dioxano/água, em temperaturas de cerca de 50 °C a cerca de 120 °C para fornecer intermediários de N- ftalimido 6-4 (etapa f). A desproteção usando hidrazina e metanol ou outro solvente adequado pode fornecer a amina 6-5 (etapa g).Esquema 6
[00102] Alternativamente, os compostos em que L é um ligador de dois átomos podem também ser preparados como mostrado no Esquema 6a. As oleofina de aldeído 4-1 (R9 = H, etapa a) podem ser obtidas com metilenotrifenilfosforano que pode ser preparado from iodeto de trifenilfosfônio de metila na presença de uma base tal como hidreto de sódio ou 1,8-diazabicicloundec-7-eno em um solvente aprótico tal como tetraidrofurano ou diclorometano em temperaturas de cerca de -78 °C a cerca de 40 °C. Hidrobromação de 6-2a com um reagente tal como 9-borabiciclo(3.3.1)nonano (9-BBN) em um solvente aprótico tal como tetraidrofurano seguido por oxidação com um oxidante tal como peróxido de hidrogênio pode gerar álcool etílico 6-3a (etapa b). Os carbinóis 6-3a podem ser tratados com ftalimida sob condições de Mitsunobu para gerar intermediários de N-ftalimido 6-5a, em que R10 = H (etapa c). A desproteção usando hidrazina e metanol ou outro solvente adequado pode fornecer a amina 6-6a (etapa f). Além disso, 6- 3a pode ser também mono-substituído com R10, em que R10 é definido como acima (etapa d), por meio de oxidação ao aldeído correspondente sob condições de Swern seguido por adição de um reagente de Grignard tal como descrito acima (Esquema 6). Os carbinóis 6-4a pode ser também tratado com ftalimida sob condições de Mitsunobu para gerar intermediários de N-ftalimido 6-5a (etapa e). A desproteção usando hidrazina e metanol ou outro solvente adequado pode fornecer a amina 6-6a (etapa f).Esquema 6a
[00103] O Esquema 6b descreve uma rotina alternativa para construção de análogos em que o ligador L é um ligante de dois átomos. A arilação catalisada por cobre de 2,4-pentano-2,4-diona com 5-1 (J. Am. Chem. Soc. 2010, 132, 8273) pode fornecer o intermediário de acetona substituído 6-1b (etapa a). A aminação reduzida (etapa b), usando quasiquer das várias condições familiares àqueles versados na técnica, pode gerar amina 6-2b. Quando um ligador contém um centro quiral, tal como com intermediário 6-2b, estes intermediários podem ser separados em suas formas isoméricas puras por meio de uma coluna quiral, ou por criatalização fracionária do sal preparadp de um ácido quiral tal como ácido (+)- e (-)-tartárico.Esquema 6b
[00104] A construção de análogos em que o grupo de ligação de etila é parte de um anel de 6 membros pode também ser realizada partindo de brometo 5-1. O acoplamento de 5-1 com 2-ciclo-hex-1- enil-4,4,5,5-tetrametil-1,3,2-dioxaborolano (Esquema 6b, etapa c) sob condições de acoplamento Suzuki padrão pode levar a alceno 6-3b. A epoxidação com reagentes padrão, tal como ácido meta- cloroperoxibenzoico (etapa d), seguida por rearranjo catalisado por paládio usando tricloridrato de índio (J. Org. Chem. 1998, 63, 8212), pode gerar cetona 6-5b. Aminação reduzida e conversão nas moléculas alvo pode ser realizada usando condições descritas acima.
[00105] A preparação de compostos em que L é um grupo de três átomos é descrita nos esquemas 7 e 8. Os precursores de aminoalquila 7-5 (Ar1-Het-Ar2-L-NH2), em que L é átomos de três carbonos, mono- ou dissubstituídos com R9, em que R9 é definido como acima; e não substituídos ou mono-substituídos com R10, em que R10 é definido como acima; podem ser preparados como mostrado no Esquema 7. Carbinóis de halofenila 7-1, em que X é Br e R9 e R10 são H, são comercialmente disponíveis. Os carbinóis 7-1 que são mono- ou dissubstituídos em R9 podem ser preparados do acetato de halofenila correspondente 7-I (etapa a) em modelo similar àquele descrito por Shin et al. Bioorg. Med. Chem. Lett. 2008, 18, páginas 4424 a 4427, seguido por redução com hidreto de metal tal como hidreto de alumínio de lítio em um solvente etéreo tal como tetraidrofurano em temperaturas em ou abaixo de cerca de 0 °C. Ambos 7-I e 7-II podem ser também mono-substituídos (etapa b ou etapa c) com R10 por meio de redução ao aldeído correspondente com hidreto de metal tal como hidreto de di-isobutilalumínio e tratamento com um reagente de Grignard tal como brometo de metilmagnésio em um modelo similar àquele descrito por Brimble et al. Org. Lett. 2012, 14, páginas 5820 a 5823. Os carbinóis 7-1 podem ser tratados com ftalimida sob condições de Mitsunobu para gerar intermediários de N- ftalimido 7-2 (etapa d).Esquema 7
[00106] O haleto pode ser convertido sob condições Miyaura para formar ésteres de boronato 7-3 (etapa e). O acoplamento dos ésteres de boronato com um bromo-heterociclo 2-3 pode ser realizado usando um catalisador de paládio, por exemplo tetracis(trifenila fosfina)paládio(0), na presença de uma base, por exemplo bicarbonato de sódio, em um sistema de solvente adequado, por exemplo dioxano/água, em temperaturas de cerca de 50 °C a cerca de 120 °C para fornecer intermediários de N-ftalimido 7-4 (etapa f). A desproteção usando hidrazina e metanol ou outro solvente adequado pode fornecer a amina 7-5 (etapa g).
[00107] Alternativamente, os compostos em que L é um ligador de três átomos podem também ser preparados como mostrado no Esquema 8. Brometo 5-1 (Ar1-Het-Ar2-Br) pode ser acoplado com um álcool alquinílico apropriado 8-1 não substituído ou mono-substituído com R10, em que R10 é definido como acima, na presença de um catalisador de paládio tal como dicloreto de bistrifenilfosfinapaládio(II), iodeto de cobre(I), e uma base tal como trietilamina, em temperaturas de cerca de 50 °C a cerca de 120 °C, para gerar os derivados de álcool alquinílico correspondentes 8-2 (etapa a). Os carbinóis resultantes 8-2 podem ser tratados com ftalimida sob condições de Mitsunobu para gerar intermediários de N- ftalimido 8-3 (etapa b) que podem ser convertidos em aminas 8-7 (etapa e) usando hidrazina e metanol ou outro solvente adequado. Os carbinóis 8-2 podem ser reduzidos usando um catalisador de metal de transição, tal como paládio sob uma atmosfera de hidrogênio para fornecer carbinóis de alquenila ou alquila totalmente saturados 8-4 não substituídos em R10. Além disso, os carbinóis 8-2 podem ser tratados com hidreto de metal tal como hidreto de alumínio de lítio para fornecer o carbinol de (E)-alquenila 8-4. Igualmente, o carbinol 8-2 pode ser protegido com um grupo tal como difenilsilila de terc- butila (TBDPS) e tratado com um reagente de hidrometalação tal como reagente de Schwartz seguido por saciamento com um eletrófilo tal como iodo elementar ou N-bromosucinimida (NBS). Alternativamente, o carbinol 8-2 pode ser tratado com um reagente de transmetalação tal como pinacol diboron para também usar em reações catalisadas por metal de transição, tais como acoplamentos Suzuki ou Negishi, para preparar carbinóis 8-4 mono- ou dissubstituídos com R9, em que R9 é definido como acima (etapa c). Após desproteção, os carbinóis resultantes 8-4 podem ser tratados com ftalimida sob condições de Mitsunobu para gerar intermediários de N-ftalimido 8-5 (etapa d) que podem ser convertidos nas aminas correspondentes 8-6. Esquema 8
[00108] Os compostos em que L é um ligador de quatro átomos podem ser preparados como mostrado no Esquema 9. Brometo 5-1 (Ar1-Het-Ar2-Br) pode ser acoplado com um álcool alquinílico apropriado 9-1 (etapa a) não substituído ou mono-substituído com R10, em que R10 é definido como acima; mono- ou dissubstituídos com R9, em que R9 é definido como acima; na presença de um catalisador de paládio tal como dicloreto de paládio(II) de bistrifenilfosfina, iodeto de cobre(I), e uma base tal como trietilamina, em temperaturas de cerca de 50 °C a cerca de 120 °C, para gerar os derivados de álcool alquinílico correspondentes 9-2. Os carbinóis resultantes 9-2 podem ser tratados com ftalimida sob condições de Mitsunobu (etapa b) para gerar intermediários de N- ftalimido 9-3 que podem ser convertidos em uma amina 9-7 (etapa e) usando hidrazina e metanol ou outros solventes adequados. Os carbinóis 9-2 podem ser reduzidos usando um catalisador de metal de transição, tal como paládio, sob uma atmosfera de hidrogênio para fornecer carbinóis de alquenila ou alquila totalmente saturados 9-4 (etapa c) não substituídos em R13. Além disso, os carbinóis 9-2 podem ser tratados com hidreto de metal tal como hidreto de alumínio de lítio para fornecer o carbinol de (E)-alquenilas 9-4 (etapa c). Igualmente, o carbinol 9-2 pode ser protegido com um grupo tal como difenilsilila de terc-butila (TBDPS) e tratado com um reagente de hidrometalação tal como reagente de Schwartz seguido por saciamento com um eletrófilo tal como iodo elementar ou NBS. Alternativamente, o carbinol 9-2 pode ser tratado com um reagente de transmetalação tal como pinacol diboron para também usar em reações catalisadas por metal de transição, tais como acoplamentos Suzuki ou Negishi, para preparar carbinóis 9-4 mono- ou dissubstituídos com R13, em que R13 é definido como o R8 acima (etapa c).Esquema 9
[00109] Após desproteção, os carbinóis resultantes 9-4 podem ser tratados com ftalimida sob condições de Mitsunobu (etapa d) para gerar intermediários de N-ftalimido 9-5 que podem ser convertidos em aminas 9-6 (etapa e) usando hidrazina e metanol ou outro solvente adequado.
[00110] As tioureias de tiazolidinona de n-arila (por exemplo, 10-4) podem ser preparadas reagindo as iminas de tiazolidinona (por exemplo, 10-3) com os isotiocianatos de triarila (por exemplo, 10-2). Como mostrado no Esquema 10, o isotiocianato de triarila pode ser preparado a partir do intermediário de fluoroamina conhecido (de US 9.029.560 B2, por exemplo, 10-1).Esquema 10
[00111] O composto de etilisotiocianato de triarila 11-3 pode ser preparado do composto de sal de amina de triariletila 11-2 usando dissulfeto de carbono na presença de trietilamina e cloreto de tosila em tetraidrofurano (THF). Como mostrado no Esquema 11, o sal de amina 11-1 origina-se do composto de brometo de triarila após um acoplamento Suzuki com fluoroborato de potássio de etilamina protegido por BOC e desproteção com TFA em diclorometano. Esquema 11
[00112] Como mostrado nos esquemas 12a e 12b, os intermediários 12-1 e 12-2 podem ser sintetizados, e em seguida usados para gerar carbamato e ureia de N-aril tiazolidina de éster (ou tioureia) 12-3 e 124.Esquema 12aEsquema 12b
[00113] O intermediário fundamental 12a-4 pode ser preparado por meio de modificação de Horner-Wadsworth Emmons da olefinação de Wittig entre benzaldeído 12a-1 e um éster de fosfonato, tal como 2- ((terc-butoxicarbonil)amino)-2-(dimetoxifosforil)acetato de metila (12a- 2), na presença de uma base, tal como 1,8-diazabiciclo[5,4,0]undec-7- eno (DBU), em temperatura ambiente. A redução do alceno por meio de hidrogenação sobre um catalisador de metal de transição, tal como paládio em carbono, pode fornecer o intermediário saturado 12a-4. A saponificação do éster em 12a-4 pode ser realizada com uma base, tal como hidróxido de lítio, em uma mistura de solvente polar, tal como tetraidrofurano, metanol e água, em temperaturas de temperatura ambiente a 50 °C para fornecer ácido 12-1. A reação de 12a-4 com um ácido forte, tal como ácido hidroclórico, em um solvente aprótico, tal como diclorometano, em temperatura ambiente, pode fornecer o sal de amina 12-2. O carbamato 12-3 pode ser preparado de ácido 12-1 por tratamento com fosforil azida de difenila e 2-imino-3-(2-isopropil-5- metilfenil)tiazolidin-4-ona na presença de uma base, tal como trietilamina, em um solvente aprótico, tal como tolueno, em temperaturas de temperatura ambiente a cerca de 60 °C. O éster 12-4 pode ser preparado de sal de amina 12-2 por tratamento com trifosgeno e 2-imino-3-(2-isopropil-5-metilfenil)tiazolidin-4-ona na presença de uma base, tal como bicarbonato de sódio, em uma mistura de solvente bifásica, tal como diclorometano-água, a 0 °C.
[00114] Estes exemplos são para propósito de ilustração e não devem ser interpretados como limitantes da descição apenas às modalidades descritas nestes exemplos.
[00115] Os materiais de partida, resgentes, e solventes que foram obtidos de fontes comerciais foram usados sem outra purificação. Solventes anidrosos foram comprados como Sure/Seal™ de Aldrich e foram usados como recebidos. Os pontos de fusão foram obtidos em um aparato de ponto de fusão capilar Thomas Hoover Unimelt ou um Sistema de Ponto de Fusão Automatizado OptiMelt do Stanford Research Systems e são não corrigidos. Os exemplos usando "temperatura ambiente" foram conduzidos em laboratórios controlados com temperaturas de cerca de 20 °C a cerca de 24 °C. As moléculas recebem seus nomes de acordo com os progrmas de nomeclatura dentro de Symyx Draw, ChemDraw ou ACD Name Pro. Se tais programas não são capazes de nomear uma molécula, a molécula é nomeada usando regras de nomeclatura convencionais. Os dados de espectro de 1H RMN são em ppm (δ) e for a registrados a 300, 400 ou 600 MHz, e dados de espectro de 13C RMN são em ppm (δ) e foram registrados a 75, 100 ou 150 MHz, a menos que de outro modo estabelecido. Exemplo 1: Preparação de (Z)-2-((terc-butoxicarbonil)amino)-3-(4-(1-(4-(trifluorometóxi)fenil)-1H-1,2,4-triazol-3-il)fenil)acrilato de metila
[00116] 4-(1-(4-trifluorometoxi)fenil)-1H-1,2,4-triazol-3-il)benzaldeido (0,5 grama (g), 1,500 millimoles (mmol)), 2-((terc-butoxicarbonil)amino)- 2-(dimetoxifosforil)acetato de metila (0,491 g, 1,650 mmol) e 1,8- diazabiciclo [5,4,0]undec-7-eno (DBU; 0,237 mililitros (mL), 1,575 mmol) são agitados juntos em diclorometano (3 mL) em temperatura ambiente durante 16 horas. A mistura reacional crua é absorvida diretamente em uma pré-coluna de sílica e purificada em uma coluna de sílica gek de 12 g usando um acetate de etila de 0 a 50% em gradiente de hexanos. O composto título é isolado como um sólido não totalmente branco (0,550 g, 73%).Exemplo 2: Preparação de 2-((terc-butoxicarbonil)amino)-3-(4-(1- (4-(trifluorometóxi)fenil)-1H-1,2,4-triazol-3-il)fenil)propanoato de metila
[00117] (Z)-2-((terc-butoxicarbonil)amino)-3-(4-(1-(4-(trifluorometóxi)fenil)-1H-1,2,4-triazol-3-il)fenil)acrilato de metila (620 mg, 1,229 mmol) é dissolvido em acdetato de etanol-etila (1:1, 50 mL) em temperatura ambiente em uma garrafa de pressão de Parr. Paládio em Carbono (5% em base seca, 50% em água; 52,3 mg, 0,012 mmol) é adicionado. A garrafa é evacuada e carregada com nitrogênio (2x), seguida por uma evacuação final e adição de gás de hidrogênio a 37 libras por polegada quadrada (psi). A mistura é agitada em temperatura ambiente durante 16 horas. A mistura reacional é filtrada, e o filtrado é concentrado. O resíduo é secado so alto vácuo a 50 °C durante 2 horas. O composto título é isolado como um sólido branco (0,617 g, 98%).Exemplo 3: Preparação de cloreto de 1-metóxi-1-oxo-3-(4-(1-(4- (trifluorometóxi)fenil)-1H-1,2,4-triazol-3-il)fenil)propan-2-amônio
[00118] 2-((terc-butoxicarbonil)amino)-3-(4-(1-(4-(trifluorometóxi)fe- nil)-1H-1,2,4-triazol-3-il)fenil)propanoato de metila (100 mg, 0,197 mmol) é dissolvido em diclorometano (3 mL). cloreto de hidrogênio a 4 M em dioxano (0,494 mL, 1,976 mmol) é adicionado. A mistura reacional é agitada em temperatura ambiente durante 3,5 horas. O solvente é evaporado sob uma corrente de nitrogênio para fornecer o composto título como um sólido branco (0,087 g, 100%).Exemplo 4: Preparação de 2-((terc-butoxicarbonil)amino)-3-(4-(1- (4-(trifluorometóxi)fenil)-1H-1,2,4-triazol-3-il)fenil)propanoico ácido
[00119] 2-((terc-butoxicarbonil)amino)-3-(4-(1-(4-(trifluorometóxi)fenil)-1H-1,2,4-triazol-3-il)fenil)propanoato de metila (110 mg, 0,217 mmol) é agitado em metanol (2 mL) e água (1 mL) em temperatura ambiente para formar uma suspensão. Hidrato de hidróxido de lítio (10,02 mg, 0,239 mmol) é adicionado e a reação é agitada em temperatura ambiente durante 2 horas. A agitação é continuada com aquecimento para 45 °C durante 2 horas. Tetraidrofurano (3 mL) é adicionado e a agitação é continuada em temperatura ambiente durante 16 horas. A mistura reacional é diluída com água e acetato de etila. A camada aquosa é acidificada com ácido hidroclórico aquoso a 1N. As camadas são separadas. A camada orgânica é secada, filtrada e concentrada. O composto título é isolado como um sólido amarelo pálido (0,080 g, 75%).Exemplo 5: Preparação de (Z)-2-(3-(3-(2-isopropil-5-metilfenil)-4- oxotiazolidin-2-ilideno)ureído)-3-(4-(1-(4-(trifluorometóxi)fenil)-1H- 1,2,4-triazol-3-il)fenil)propanoato de metila
[00120] Cloreto de 1-metóxi-1-oxo-3-(4-(1-(4-(trifluorometóxi)fenil)- 1H-1,2,4-triazol-3-il)fenil)propan-2-amônio (87 mg, 0,196 mmol) é agitado em diclorometano (10 mL) e água (5 mL) a 0 °C com a adição de bicarbonato de sódio (165 mg, 1,965 mmol) durante 15 minutos. Trifosgeno (38,5 mg, 0,130 mmol) é adicionado e a mistura é agitada durante 45 minutos. A mistura é passada através de um cartucho de retenção de água e a fase orgânica é deixada gotejar diretamente emu ma solução agitada de 2-imino-3-(2-isopropil-5-metilfenil)tiazolidin-4- ona (53,7 mg, 0,216 mmol) e trietilamina (137 μL, 0,982 mmol) em diclorometano (5 mL). A mistura reacional é agitada em temperatura ambiente durante 2 horas. A mistura reacional crua é absorvida em silica gel. A purificação por cromatografia de sílica gel (12 g de coluna de sílica gel) eluindo com um acetate de etila a 0 a 50% em gradiente de hexanos fornece o composto título como um óleo amarelo que solidifica para uma espuma sólida sobre evaporação prolongada (0,068 g, 51%).Exemplo 6: Preparação de (Z)-(1-(3-(3-(2-isopropil-5-metilfenil)-4- oxotiazolidin-2-ilideno)ureído)-2-(4-(1-(4-(trifluorometóxi)fenil)-1H- 1,2,4-triazol-3-il)fenil)etil)carbamato de terc-butila
[00121] Ácido 2-((terc-butoxicarbonil)amino)-3-(4-(1-(4-(trifluorometóxi)fenil)-1H-1,2,4-triazol-3-il)fenil)propanoico (80 mg,0,162 mmol) e 2-imino-3-(2-isopropil-5-metilfenil)tiazolidin-4-ona (40,3 mg, 0,162 mmol) são agitados juntos em tolueno (5 mL) em temperature ambiente. Trietilamina (0,136 mL, 0,976 mmol) e azida de difenilfosforila (67,1 mg, 0,244 mmol) são adicionados sequencialmente. Após 1 hora, uma porção adicional de 2-imino-3-(2-isopropil-5-metilfenil)tiazolidin-4- ona (40,3 mg, 0,162 mmol) é adicionada e a reação é aquecida para 50 °C durante 90 minutos e em seguida agitada em temperatura ambiente durante 16 horas. A mistura reacional crua é absorvida sobre sílica gel. A purificação por cromatografia de sílica gel (4 g de coluna de silica gel) eluindo com um acetate de etila a 0 a 50% em gradiente de hexanos forneceu o composto título como um sólido amarelo pálido (0,060 g, 50%).
[00122] Usando os procedimentos descritos aqui a lista seguinte de moléculas é fornecida como exemplo (Tabela 1).
[00123] Usando os procedimentos descritos aqui, a seguinte lista de molécula é também fornecida como exemplos (Tabela 2).
[00124] A lagarta da beterraba tem poucos parasitas, doenças, ou prepadores eficazespara diminuir sua população para diminuir sua população. A BAW infesta muitas ervas daninhas, arvores, gramas, legumes, e colheitas de campo. Em vários lugares, ela é uma preocupação econômica em aspargo, algodão, milho, soja, tabaco, alfafa, beterrabas sacarinas, pimentas, tomates, batatas, cebolas, ervilhas, gorassóis, e cítricos, entre outras plantas. A larva do repolho é um membro da família da traça Noctuidae. Ela é encontrada em todo o mundo. E ataca repolho, couve-flor, brócolis, couve de bruxelas, tomates, pepinos, batatas, couve, nabos, mostarda, pimentas, berinjela, melanciais, melões, abóbora, melão rosado, ervilhas, feijão, couves galesas, alface, espinafre, aipo, salsinha, beterraba, ervilhas, alfalfa, soja, e algodão. Esta espécie é muito destrutiva para as plantas devido ao seu consume voraz. No caso do repolho, entretanto, ela alimenta-se não apenas na folhas do invólucro, mas também pode penetrar na cabeça em desenvolvimento. As larvas consomem três vezes o seu peso na planta diariamente. Os sítios de alimentação são marcados por grande acúmulo de material fecal úmido pegajoso.
[00125] Consequentemente, porque os fatores acima o controle destas pestes é importante. Além disso, as moléculas que controlam estas pestes (BAW e CL), que são conhecidas como pestes de mastigação, são úteis no controle de outras pestes que mastigam plantas.
[00126] Certas moléculas descritas no documento foram testadas contra BAW e CL usando os procedimentos descritos nos exemplos seguintes. Na descrição dos resultados, o "BAW & CL Rating Table" foi usado (veja Seção de Tabela).
[00127] Os Bioensaios em BAW foram conduzidos usando um ensaio de bandeja de dieta de 128 cavidades. Uma a cinco larvas de segundo íntar de BAW foram colocadas em cada cavidade (3 mL) da bandeja de dieta que foi previamente carregada com 1 mL de dieta artificial a qual 50 μg/cm2 do composto teste (dissolvido em 50 μL de mistura de acetona-água de 90:10) foram aplicados (a cada uma das oito cavidades) e em seguida deixados secar. As bandejas foram revestidas com uma cobertura autoadesiva clara e mantidas a 25 °C, 14:10 de luz-escuridão durante cinco a sete dias. A mortalidade percentual foi registrada quanto à larvas em cada cavidade; a atividade nas oito cavidades foi em seguida calculada. Os resultados são indicados na tabela intitulada "Tabela ABC: Resultados Biológicos" (veja Seção de Tabela).
[00128] Os bioensaio em CL foram conduzidos usando um ensaio de bandeja de dieta de 128 cavidades. Um a cinco larvas de CL de Segundo ínstar foram colocadas em cada cavidade (3 mL) da bandeja de dieta que foi previamente carregada com 1 mL de dieta artificial a qual 50 μg/cm2 do composto teste (dissolvido em 50 μL de mistura de 90:10 de acetona-água) foram aplicados (a cada uma das oito cavidades) e em seguida deixados secar. As bandejas foram revestidas com uma cobertura autoadesiva clara e mantidas a 25 °C, 14:10 de luz- escuridão durante cinco a sete dias. A mortalidade percentual foi registrada quanto à larvas em cada cavidade; a atividade nas oito cavidades foi em seguida calculada. Os resultados são indicados na tabela intitulada "Table ABC: Resultados Biológicos" (veja Seção de Tabela).
[00129] O GPA é a peste de pulgão mais significante de árvores de pêssego, que causa crescimento diminuído, murchamento das folhas, e a morte de vários tecidos. É também arriscado porque ele age como um vetor para o transporte de vírus de planta, tal como vírus de batata Y e vírus de enrolador de folhas de batata para memebros da família de erva-moura/batata Solanaceae, e vários vírus de mosaico para muitas outras colheitas de alimento. O GPA pulgão ataca tais plantas como brócolis, bardana, repolho, cenoura, couve-floro, daicôn, berinjela, feijão verde, alface, macadâmia, mamão, pimentas, batatas doces, tomates, agrião, e abobrinha, entre outras plantas. O GPA também ataca muitas colheitas ornamentais tais como cravo, crisântemo, repolho branco de fluorescência, poinsétia, e rosas. O GPA desenvolveu resistência a muitos pesticidas. Consequentemente, por causa dos fatores acima o controle desta peste é importante. Além disso, as moléculas que controlam esta peste (GPA), que é conhecida como uma peste sugadora, são úteis no controle de outras pestes que sugam as plantas.
[00130] Certas moléculas descritas no documento foram testadas contra GPA usando os procedimentos descritos no exemplo seguinte. Na descrição dos resultados, a "Tabela de Classificação de GPA" foi usada (veja Seção de Tabela).
[00131] Mudas de repolho desenvolvidas em potes de 3 polegadas, com 2 a 3 pequenas folhas verdadeiras (3 a 5 cm), foram usadas como substrato de teste. As mudas foram infestadas com 20 a 50 GPA (estágios ninfa e adulto sem asas) um dia antes da aplicação química. Quatro potes com mudas individuais foram usados para cada tratamento. Os compostos teste (2 mg) foram dissolvidos em 2 mL de solvente de acetona/metanol (1:1), formando soluções de matéria-prima de 1000 ppm de composto teste. As soluções de matéria-prima foram diluídas 5X com 0,025% de Tween 20 em água para obter a solução a 200 ppm de composto teste. Um vaporizador do tipo aspirador manual foi usado para vaporização de uma solução para ambos os lados de folhas de repolho até o escoamento. As plantas de referência (checagem de solvente) foram vaporizadas com o diluente apenas contendo 20% por volume de solvente de acetona/metanol (1:1). As plantas tratadas foram mantidas em um ambiente de manutenção durante três dias a aproximadamente 25 °C e umidade relativa ambiente (RH) antes da classificação. A avaliação foi conduzida por contagem do número dos pulgões por planta sob um microscópio. O controle percentual foi medido usando-se a fórmula de correção de Abbott (W.S. Abbott, "A Method of Computing the Effectiveness of an Insecticide" J. Econ. Entomol. 18 (1925), pp.265-267) como segue:
[00132] em que
[00133] X = N° de pulgões vivos em checagem de plantas de solvente e
[00134] Y = N° de pulgões vivos em plantas tratadas
[00135] Os resultados são indicados na tabela intitulada "Tabela ABC: Resultados biológicos" (veja Seção de Tabela).
[00136] YFM prefere se alimentar de seres humanos durante o dia e é mais frequentemente encontrado em ou próximo de habitações humanas. O YFM é um vetor para transmissão de várias doenças. É um mosquito que pode espalhar vírus de febre da dengue e febre amarela. A febra amarela é a segunda doença transmitida por mosquito mais perigosa após a malária. A febre amarela é uma doença hemorrágica viral aguda e até 50% de pessoas gravemente afetadas sem o tratamento morrerão a de febre amarela. Há uma estimative de 200.000 casos de febre amarela, que causam 30.000 mortes, em todo o mundo a cada ano. A febre da dengue é uma doença viral desagradácvel; é às vezes chamada de "breakbone fever (dengue)" ou "febre do coração partido" por causa da dor intensa que ela pode produzir. A febre da dengue mata cerca de 20.000 pessoas anualmente. Consequentemente, por causa dos fatores acima o controle desta peste é importante. Além disso, as moléculas que controlam esta peste (YFM), que é conhecida como uma peste sugadora, são úteis no controle de outras pestes que causam humano e animal.
[00137] Certas moléculas descritas no documento foram testadas contra YFM usando os procedimentos descritos no parágrafo seguinte. Na descrição dos resultados, o "Tabela de Classificação de YFM" foi usado (veja Seção de Tabela).
[00138] Placas mestres contendo 400 μg de uma molécula dissolvida em 100 μL de sulfóxido de dimetila (DMSO) (equivalentes a uma solução de 4000 ppm) são usados. Uma placa mestre de moléculas montadas contém 15 μL por cavidade. A esta placa, 135 μL de uma mistura de 90:10 de água:acetona é adicionada a cada cavidade. Um robô (Biomek® NXP Laboratory Automation Workstation) é programdo para dispensar asipirações de 15 μL da placa mestre em uma placa rasa de 96 cavidades vazia (placa "filha"). Há 6 repetições (placas "filhas") criadas por mestre. As placas filhas criadas são, em seguida, imediatamente infestadas com larvas de YFM.
[00139] No dia anterior às placas serem tratadas, ovos de mosquito são colocados em água Millipore contendo pó de fígado para começarem a eclodir (4 g em 400 mL). Após as placas filhas serem criadas usando o robô, elas são infestadas com 220 μL da mistura de pó de fígado/mosquito larval (cerca de larvas de 1 dia de idade). Após as placas serem infestadas com larvas de mosquito, uma tampa não evaporative é usada para cobrir a placa para reduzir a secagem. As placas são mantidas em temperatura ambiente durante 3 dias antes da classificação. Após 3 dias, cada cavidade é observada e marcada com base na mortalidade.
[00140] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser formuladas em sais de adição de ácido agricolamente aceitáveis. Por meio de um exemplo não limitante, uma função de amina pode formar sais com ácidos hidroclórico, hidrobrômico, sulfúrico, fosfórico, acético, benzoico, cítrico, malônico, salicílico, málico, fumárico, oxálico, succínico, tartárico, lático, glucônico, ascórbico, maleico, aspártico, benzenossulfõnico, metanossulfõnico, etanossulfônico, hidroxil- metanossulfônico, e hidroxietanossulfônico. Além disso, por meio de um exemplo não limitante, uma função de ácido pode formar sais que incluem aqueles derivados de metais de álcali ou alcalinos terrosos e aqueles derivados de ammonia e aminas. Os exemplos de cations preferidos inlcuem sódio, potássio, e magnésio.
[00141] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser formuladas em derivados de sal. Por meio de um exemplo não limitante, um derivado de sal pode ser preparado pondo em contato uma base livre com uma quantidade suficiente do ácido desejado para produzir um sal. Uma base livre pode ser regenerada tratando-se o sal com uma solução de base aquosa diluída adequada tais como hidróxido de sódio aquoso diluído, carbonato de potássio, amônia, e bicarbonate de sódio. Como um exemplo, em muitos casos, um pesticida, tal como 2,4-D, é feito de maneira mais solúvel convertendo-o em seu sal de dimetilamina.
[00142] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser formuladas em complexos estáveis com um solvente, de tal forma que o complexo permanece intacto após o solvente não complexado ser removido. Estes complexos são frequentemente referidos como "solvatos". Entretanto, é particularmente desejávelformar hidratos estáveis com água como o solvente.
[00143] As moléculas de Fórmula Um e/ou Fórmula Dois pode ser feitas em derivados de éster. Estes derivados de éster podem em seguida ser aplicados da mesma maneira que as moléculas descritas no documento são aplicadas.
[00144] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser feitas como vários polimorfos de cristal. O polimorfismo é importante no desenvolvimento de materiais agroquímicos, visto que diferentes polimorfos de cristal ou estruturas da mesma molécula podem ter propriedades físicas vastamente diferentes e desempenhos biológicos.
[00145] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser feitas com isótopos diferentes. De importância particular são moléculas tendo 2H (também conhecidas como deutério) no lugar de 1H.
[00146] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser feitas com diferentes radionucleotídeos. De importância particular são moléculas tendo 14C.
[00147] As moléculas de Fórmula Um e/ou Fórmula Dois podem existir como um ou mais estereoisômeros. Desse modo, certas moléculas podem ser produzidas como misturas racêmicas. Será apreciado por aqueles versados na técnica que um estereoisômero pode ser mais ativo do que os outros estereoisômeros. Os estereoisômeros individuais podem ser obtidos por procedimentos sintéticos conhecidos, por procedimentos sintéticos convencionais usando materiais de partida resolvidos, ou por procedimentos de resolução convencionais. Certas moléculas descritas no documento podem existir como dois ou mais isômeros. Os vários isômeros incluem isômeros geométricos, diastereômeros, e enantiômeros. Desse modo, as moléculas descritas no documento incluem isômeros geométricos, misturas racêmicas, estereoisômeros individuais, e misturas opcionalmente ativas. Será apreciado por aqueles versados na técnica que um isômero pode ser mais eficaz do que os outros. As estruturas descritas na presente descrição são retiradas de apenas uma forma geométrica para clareza, porém são destinadas a representar todas as formas geométricas da molécula.
[00148] Em outra modalidade, moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas em combinação (tal como, em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com um ou mais compostos, cada qual tendo um modo de ação que é igual, similar, ou diferente do modo de ação ("MoA") das moléculas de Fórmula Um e/ou Fórmula Dois. Os modos de ação incluem, por exemplo, os seguintes: inibidores de acetilcolinesterase (AChE); antagonistas de canal de cloreto controlado por GABA; moduladores de canal de sódio; agonistas de acetilcolina nicotínicos (nAChR); ativadores alostéricos de receptor de acetil colina nicotínicos (nAChR); ativadores de canal de cloreto; Miméticos de hormônio juvenil; inibidores não específicos miscelanáceos (múltiplos sítios); Bloqueadores de alimentação de homopteran seletivos; inibidores de crescimento de ácaro; Distuptores microbianos de membranas de intestino de inseto; inibidores de ATP sintase mitocondrial; Desacopladores de fosforilação oxidativa por meio da rupture do gradiente de próton; bloqueadores de canal de receptor de acetilcolina nicotínico (nAChR); inibidores de de biossíntese de quitina, tipo 0; inibidores de de biossíntese de quitina, tipo 1; disruptor de muda, Dipteran; Agonistas de receptor de ecdisona; Agonistas de receptor de octopamina; Inibidores de transporte de elétron de complexo mitocondrial III; Inibidores de transporte de elétron de complexo mitocondrial I; bloqueadores de canal de sódio dependents de voltagem; inibidores de acetil CoA carboxilase; Inibidores de transporte de elétron de complexo mitocondrial IV; Inibidores de transporte de elétron de complexo mitocondrial II; e Moduladores de receptor de rianodina.
[00149] Em outra modalidade, moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas em combinação (tal como, em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com um ou mais compostos tendo propriedades acaricidas, algicidas, avicidas, bactericidas, fungicidas, herbicidas, inseticidas, moluscicidas, nematicidas, rodenticidas, e/ou virucidais.
[00150] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas em combinação (tal como, em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com com um ou mais compostos que são inseticidas, repelentes de aves, quimioesterilantes, protetores de herbicida, atrativos de inseto, repelentes de inseto, repelentes de mamíferos, disruptores de acasalamento, ativadores de planta, reguladores de crescimento de planta, e/ou sinérgicos.
[00151] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas em combinação (tal como, em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com com um ou mais dos seguintes compostos -
[00152] Brometo de (3-etoxipropil)mercúrio, 1,2-dicloropropano, 1,3- dicloropropeno, 1-metilciclopropeno, 1-naftol, 2-(octiltio)etanol, ácido 2,3,5-tri-iodobenzoico, 2,3,6-TBA, 2,3,6-TBA-dimetilamônio, 2,3,6-TBA- lítio, 2,3,6-TBA-potássio, 2,3,6-TBA-sódio, 2,4,5-T, 2,4,5-T-2-butoxipropila, 2,4,5-T-2-etil-hexila, 2,4,5-T-3-butoxipropila, 2,4,5-TB, 2,4,5-T-butometila, 2,4,5-T-butotila, 2,4,5-T-butila, 2,4,5-T-isobutila, 2,4,5-T-isoctila, 2,4,5-T-isopropila, 2,4,5-T-metila, 2,4,5-T-pentila, 2,4,5- T-sódio, 2,4,5-T-trietilamônio, 2,4,5-T-trolamina, 2,4-D, 2,4-D-2-butoxipropila, 2,4-D-2-etil-hexila, 2,4-D-3-butoxipropila, 2,4-D-amônio, 2,4-DB, 2,4-DB-butila, 2,4-DB-dimetilamônio, 2,4-DB-isoctila, 2,4-DB- potássio, 2,4-DB-sódio, 2,4-D-butotila, 2,4-D-butila, 2,4-D-dietilamônio, 2,4-D-dimetilamônio, 2,4-D-diolamina, 2,4-D-dodecilamônio, 2,4-DEB, 2,4-DEP, 2,4-D-etila, 2,4-D-heptilamônio, 2,4-D-isobutila, 2,4-D-isoctila, 2,4-D-isopropila, 2,4-D-isopropilamônio, 2,4-D-lítio, 2,4-D-meptila, 2,4- D-metila, 2,4-D-octila, 2,4-D-pentila, 2,4-D-potássio, 2,4-D-propila, 2,4- D-sódio, 2,4-D-tefurila, 2,4-D-tetradecilamônio, 2,4-D-trietilamônio, 2,4- D-tris(2-hidroxipropil)amônio, 2,4-D-trolamina, 2iP, cloreto de 2- metoxietilmercúrio, 2-fenilfenol, 3,4-DA, 3,4-DB, 3,4-DP, 4- aminopiridina, 4-CPA, 4-CPA-diolamina, 4-CPA-potássio, 4-CPA-sódio, 4-CPB, 4-CPP, álcool 4-hidroxifenetílico, sulfato de 8-hidroxiquinolina, 8-fenilmercurioxiquinolina, abamectina, ácido abscísico ACC, acefato, acequinocila, acetamiprida, acetion, acetoclor, acetofos, acetoprol, acibenzolar, acibenzolar-S-metila, acifluorfen, acifluorfen-metila, acifluorfen-sódio, aclonifen, acrep, acrinatrina, acroleina, acrilonitrila, acinonapir, acipetacs, acipetacs-cobre, acipetacs-zinco, afidopiropen, alaclor, alanicarbe, albendazol, aldicarbe, aldimorf, aldoxicarbe, aldrina, aletrina, alicina, alidoclor, alosamidina, aloxidim, aloxidim-sódio, álcool alílico, alixicarbe, alorac, alfa-cipermetrina, alfa-endosulfan, ametoctradina, ametridiona, ametrina, amibuzina, amicarbazona, amicartiazol, amidition, amidoflumet, amidosulfuron, aminocarbe, aminociclopiraclor, aminociclopiraclor-metila, aminociclopiraclor- potássio, aminopiralid, aminopiralid-potássio, aminopiralid-tris(2- hidroxipropil)amônio, aminopirifen, amiprofos-metila, amiprofos, amisulbrom, amiton, amiton oxalato, amitraz, amitrol, amônio sulfamato, amônio α-naftalenoacetato, amobam, ampropilfos, anabasina, sulfato de anabasina, ancimidol, anilazina, anilofos, anisuron, antraquinona, antu, apholato, aramite, óxido arsenoso, asomato, aspirina, asulam, asulam-potássio, asulam-sódio, atidation, atraton, atrazina, aureofungina, aviglicina, cloridrato de aviglicina, azaconazol, azadiractina, azafenidina, azametifos, azimsulfuron, azinfos-etila, azinfos-metila, aziprotrina, azitiram, azobenzeno, azociclotina, azotoato, azoxistrobina, bacmedesh, barban, hexafluorossilicato de bário, polissulfeto de bário, bartrina, BCPC, beflubutamida, benalaxila, benalaxil-M, benazolina, benazolin-dimetilamônio, benazolin-etila, benazolin-potássio, bencarbazona, benclotiaz, bendiocarbe, benfluralina, benfuracarbe, benfuresato, benodanil, benomila, benoxacor, benoxafos, benquinox, bensulfuron, bensulfuron-metila, bensulida, bensultap, bentaluron, bentazona, bentazone-sódio, bentiavalicarbe, bentiavalicarb-isopropila, bentiazol, bentranil, benzadox, benzadox-amônio, cloreto de benzalcônio, benzamacril, benzamacril-isobutila, benzamorf, benzfendizona, benzipram, benzobiciclon, benzofenap, benzofluor, ácido benzohidroxâmico, benzovindiflupir, benzoximato, benzoilprop, benzoilprop-etila, benzpirimoxan, benztiazuron, benzoato de benzila, benziladenina, berberina, cloreto de berberina, beta-ciflutrina, beta-cipermetrina, betoxazina, biciclopirona, bifenazato, bifenox, bifentrina, bifujunzhi, bilanafos, bilanafos-sódio, binapacrila, bingqingxiao, bioalletrina, bioetanometrina, biopermetrina, bioresmetrina, bifenila, bisazir, bismertiazol, bispiribac, bispiribac-sódio, bistrifluron, bitertanol, bitionol, bixafen, blasticidin-S, borax, mistura de Bordeaux, ácido bórico, boscalida, brassinolida, brassinolida-etila, brevicomina, brodifacoum, brofenvalerato, broflanilida, broflutrinato, bromacil, bromacil-lítio, bromacil-sódio, alfa-bromadiolona, bromadiolona, brometalina, brometrina, bromfenvinfos, bromoacetamida, bromobonil, bromobutida, bromociclen, bromo-DDT, bromofenoxim, bromofos, bromofos-etila, bromopropilato, bromotalonila, bromoxinila, butirato de bromoxinila, heptanoato de bromoxinila, octanoato de bromoxinila, bromoxinil- potássio, brompirazon, bromuconazol, bronopol, bucarpolato, bufencarbe, buminafos, bupirimato, buprofezina, mistura de Burgundi, busulfan, butacarbe, butaclor, butafenacil, butamifos, butatiofos, butenaclor, butetrina, butidazol, butiobato, butiuron, butocarboxim, butonato, butopironoxila, butoxicarboxim, butralina, butroxidim, buturon, butilamina, butilato, ácido cacodiílico, cadusafos, cafenstrol, arsenato de cálcio, clorato de cálcio, cianamida de cálcio, polissulfeto de cálcio, calvinfos, cambendiclor, canfeclor, cânfora, captafol, captan, carbamorf, carbanolato, carbarila, carbasulam, carbendazim, carbendazim benzenossulfonato, sulfeto de carbendazim, carbetamida, carbofuran, dissulfeto de carbono, tetracloreto de carbono, carbofenotion, carbosulfan, carboxazol, carbóxido, carboxina, carfentrazona, carfentrazona-etila, carpropamida, cartap, cloridrato de cartap, carvacrol, carvona, CDEA, celocidina, CEPC, ceralure, mistura de Ceshunt, cinometionat, quitosan, clobentiazona, clometoxifen, cloralose, cloramben, cloramben-amônio, cloramben-diolamina, cloramben-metila, cloramben-metilamônio, cloramben-sódio, cloramina fosphorus, cloramfenicol, cloraniformetan, cloranila, cloranocrila, clorantraniliprol, clorazifop, clorazifop-propargila, clorazina, clorbenside, clorbenzuron, clorbiciclen, clorbromuron, clorbufam, clordano, clordecona, clordimeform, clordimeform hidrocloride, clorempentrina, cloretoxifos, cloreturon, clorfenac, clorfenac-amônio, clorfenac-sódio, clorfenapir, clorfenazol, clorfenetol, clorfenprop, clorfenson, clorfensulfeto, clorfenvinfos, clorfluazuron, clorflurazol, clorfluren, clorfluren-metila, clorflurenol, clorflurenol-metila, cloridazon, clorimuron, clorimuron-etila, clormefos, clormequat, cloreto de clormequat, clornidina, clornitrofen, clorobenzilato, clorodinitronaftalenos, clorofórmio, cloromebufórmio, clorometiuron, cloroneb, clorofacinona, clorofacinona-sódio, cloropicrina, cloropon, cloropraletrina, cloropropilato, clorotalonila, clorotoluron, cloroxuron, cloroxinil, clorfônio, cloreto de clorfônio, clorfoxim, clorprazofos, clorprocarbe, clorprofam, clorpirifos, clorpirifos-metila, clorquinox, clorsulfuron, clortal, clortal- dimetila, clortal-monometila, clortiamida, clortiofos, clozolinato, cloreto de colina, cromafenozida, cinerina I, cinerina II, cinerinas, cinidon-etila, cimetilina, cinossulfurona, ciobutida, cisanilida, cismetrina, clacifos, cletodim, climbazol, cliodinato, clodinafop, clodinafop-propargila, cloetocarbe, clofencet, clofencet-potássio, clofentezina, ácido clofibric, clofop, clofop-isobutila, clomazona, clomeprop, cloprop, cloproxidim, clopiralida, clopiralida-metila, clopiralida-olamina, clopiralida-potássio, clopiralida-tris(2-hidroxipropil)amônio, cloquintocet, cloquintocet-mexila, cloransulam, cloransulam-metila, closantel, clotianidina, clotrimazol, cloxifonac, cloxifonac-sódio, CMA, codlelure, colofonato, acetato de cobre, acetoarsenito de cobre, arsenato de cobre, carbonato de cobre, básico, hidróxido de de cobre, naftenato de cobre, oleato de cobre, oxicloreto de cobre, silicato de cobre, sulfato de cobre, cromato de zinco de cobre, coumaclor, coumafurila, coumafos, coumatetralila, coumitoato, coumoxistrobina, CPMC, CPMF, CPPC, credazina, cresol, crimidina, crotamiton, crotoxifos, crufomato, criolite, cue-lure, cufraneb, cumiluron, cuprobam, óxido cuproso, curcumenol, cianamida, cianatrina, cianazina, cianofenfos, cianofos, ciantoato, ciantraniliprol, ciazofamida, cibutrina, ciclafuramida, ciclanilida, ciclaniliprol, cicletrina, cicloato, ciclo-heximida, cicloprato, cicloprotrina, ciclopiranil, ciclopirimorato, ciclossulfamuron, cicloxidim, cicluron, cienopirafen, ciflufenamida, ciflumetofeno, ciflutrina, ci-halodiamida, ci-halofop, ci- halofop-butila, ci-halotrina, ci-hexatina, cimiazol, cloridrato de cimiazol, cimoxanil, ciometrinil, cipendazol, cipermetrina, ciperquat, cloreto de ciperquat, cifenotrina, ciprazina, ciprazol, ciproconazol, ciprodinila, ciprofuram, cipromida, ciprosulfamida, ciromazina, citioato, daimuron, dalapon, dalapon-cálcio, dalapon-magnésio, dalapon-sódio, daminozida, daioutong, dazomet, dazomet-sódio, DBCP, d-canfor, DCIP, DCPTA, DDT, debacarbe, decafentina, decarbofuran, ácido desidroacético, delaclor, deltametrina, demephion, demefiona-O, demefiona-S, demeton, demeton-metila, demeton-O, demeton-O- metila, demeton-S, demeton-S-metila, demeton-S-metilsulphon, desmedipham, desmetrina, d-fanshiluquebingjuzhi, diafentiuron, dialifos, di-allato, diamidafos, terra diatomácea, diazinon, ftalato de dibutila, succinato de dibutila, dicamba, dicamba-diglicolamina, dicamba-dimetilamônio, dicamba-diolamina, dicamba-isopropilamônio, dicamba-metila, dicamba-olamina, dicamba-potássio, dicamba-sódio, dicamba-trolamina, dicapton, diclobenil, diclobentiazox, diclofention, diclofluanida, diclona, dicloralureia, diclorbenzuron, diclorflurenol, diclorflurenol-metila, diclormato, diclormida, diclorofeno, diclorprop, diclorprop-2-etil-hexila, diclorprop-butotila, diclorprop-dimetilamônio, diclorprop-etilamônio, diclorprop-isoctila, diclorprop-metila, diclorprop-P, diclorprop-P-2-etil-hexila, diclorprop-P-dimetilamônio, diclorprop- potássio, diclorprop-P-potássio, diclorprop-P-sódio, diclorprop-sódio, diclorvos, diclozolina, diclobutrazol, diclocimet, diclofop, diclofop-metila, diclomezina, diclomezina-sódio, dicloran, dicloromezotiaz, diclosulam, dicofol, dicoumarol, dicresila, dicrotofos, diciclanil, diciclonon, dieldrina, dienoclor, dietanquat, dicloreto de dietanquat, dietatila, dietatil-etila, dietofencarbe, dietolato, pirocarbonato de dietila, dietiltoluamida, difenacoum, difenoconazol, difenopenten, difenopenten-etila, difenoxuron, difenzoquat, metilsulfato de difenzoquat, difetialona, diflovidazina, diflubenzuron, diflufenican, diflufenzopir, diflufenzopir- sódio, diflumetorim, dikegulac, dicegulac-sódio, dilor, dimatif, dimeflutrina, dimefox, dimefuron, dimepiperato, dimetaclona, dimetan, dimetacarbe, dimetaclor, dimetametrina, dimetenamida, dimetenamid- P, dimetipina, dimetirimol, dimetoato, dimetomorf, dimetrina, carbato de dimetila, ftalato de dimetila, dimetilvinfos, dimetilan, dimexano, dimidazon, dimoxistrobina, dinex, dinex-diclexina, dingjunezuo, diniconazol, diniconazol-M, dinitramina, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinofenato, dinopenton, dinoprop, dinosam, dinoseb, dinoseb acetato, dinoseb-amônio, dinoseb-diolamina, dinoseb- sódio, dinoseb-trolamina, dinossulfona, dinotefuran, dinoterb, dinoterb acetato, dinoterbon, diofenolan, dioxabenzofos, dioxacarbe, dioxationa, difacinona, diphacinona-sódio, difenamida, difenil sulfona, difenilamina, dipropalina, dipropetrina, dipimetitrona, dipiritiona, diquat, diquat dibrometo, disparlure, disul, disulfiram, dissulfoton, dissul-sódio, ditalinfos, ditianon, diticrofos, ditioéter, ditiopir, diuron, d-limoneno, DMPA, DNOC, DNOC-amônio, DNOC-potássio, DNOC-sódio, dodemorf, acetato de dodemorf, benzoato de dodemorf, dodicina, cloridrato de dodicina, dodicina-sódio, dodina, dofenapina, dominicalure, doramectina, drazoxolon, DSMA, dufulina, EBEP, EBP, ecdisterona, edifenfos, eglinazina, eglinazina-etila, emamectina, benzoato de emamectina, EMPC, empentrina, endossulfan, endotal, endotal-diamônio, endotal-dipotássio, endotal-disódio, endotiona, endrina, enestroburina, enoxastrobina, EPN, epocoleona, epofenonano, epoxiconazol, eprinomectina, epronaz, epsilon-metoflutrina, epsilon- monfluorotrina, EPTC, erbon, ergocalciferol, erlujixiancaoan, esdépalétrina, esfenvalerato, esprocarbe, etacelasil, etaconazol, etafos, etem, etaboxam, etaclor, etalfluralina, etametsulfuron, etametsulfuron- metila, etaproclor, etefon, etidimuron, etiofencarbe, etiolato, etion, etiozina, etiprol, etirimol, etoate-metila, etofumesato, eto-hexadiol, etoprofos, etoxifeno, etoxifen-etila, etoxiquina, etoxisulfuron, eticlozato, formiato de etila, α-naftalenoacetato de etila, etil-DDD, etileno, dibrometo de etileno, dicloreto de etileno, óxido de etileno, etilicina, etilmercúrio mercaptída de 2,3-di-hidroxipropila, acetato, brometo de etilmercúrio, cloreto de etilmercúrio, fosfato de etilmercúrio, etinofeno, etnipromida, etobenzanid, etofenprox, etoxazol, etridiazol, etrinfos, eugenol, EXD, famoxadona, fanfur, fenamidona, fenaminossulf, fenaminstrobina, fenamifos, fenapanil, fenarimol, fenasulam, fenazaflor, fenazaquina, fenbuconazol, fenbutatin oxide, fenclorazol, fenclorazol- etila, fenclorfos, fenclorim, fenetacarbe, fenflutrina, fenfuram, fenexamida, fenitropan, fenitrotiona, fenjuntong, fenobucarbe, fenoprop, fenoprop-3-butoxipropila, fenoprop-butometila, fenoprop-butotila, fenoprop-butila, fenoprop-isoctila, fenoprop-metila, fenoprop-potássio, fenotiocarbe, fenoxacrim, fenoxanil, fenoxaprop, fenoxaprop-etila, fenoxaprop-P, fenoxaprop-P-etila, fenoxasulfona, fenoxicarbe, fenpiclonil, fenpicoxamida, fenpiritrina, fenpropatrina, fenpropidina, fenpropimorf, fenpirazamina, fenpiroximato, fenquinotriona, fenridazon, fenridazon-potássio, fenridazon-propila, fenson, fensulfotion, fenteracol, fentiaprop, fentiaprop-etila, fentiona, fention-etila, fentina, acetato de fentina, cloreto de fentina, hidróxido de fentina, fentrazamida, fentrifanil, fenuron, fenuron TCA, fenvalerato, ferbam, ferinzona, sulfato ferroso, fipronila, flamprop, flamprop-isopropila, flamprop-M, flamprop-metila, flamprop-M-isopropila, flamprop-M-metila, flazasulfuron, flocoumafen, flometoquina, flonicamida, florasulam, florpirauxifeno, florilpicoxamida, fluacripirim, fluazaindolizina, fluazifop, fluazifop-butila, fluazifop-metila, fluazifop-P, fluazifop-P-butila, fluazinam, fluazolato, fluazuron, flubendiamida, flubenzimina, flucarbazona, flucarbazona-sódio, flucetossulfurona, flucloralina, flucofurona, flucicloxurona, flucitrinato, fludioxonila, fluenetila, fluensulfona, flufenacet, flufenerim, flufenican, flufenoxuron, flufenoxistrobina, flufenprox, flufenpir, flufenpir-etila, flufiprol, fluhexafon, fluindapir, flumetrina, flumetover, flumetralina, flumetsulam, flumezina, flumiclorac, flumiclorac-pentila, flumioxazina, flumipropina, flumorf, fluometuron, fluopicolide, fluopiram, fluorbensida, fluoridamida, fluoroacetamida, fluorodifen, fluoroglicofen, fluoroglicofen- etila, fluoroimida, fluoromidina, fluoronitrofen, fluopimomida, fluotiuron, fluotrimazol, fluoxastrobina, flupoxam, flupropacil, flupropadina, flupropanato, flupropanato-sódio, flupiradifurona, flupirimina, flupirsulfuron, flupirsulfuron-metila, flupirsulfuron-metil-sódio, fluquinconazol, flurazol, flurenol, flurenol-butila, flurenol-metila, fluridona, flurocloridona, fluroxipir, fluroxipir-butometila, fluroxipir- meptila, flurprimidol, flursulamida, flurtamona, flusilazol, flusulfamida, flutiacet, flutiacet-metila, flutianil, flutolanil, flutriafol, fluvalinato, fluxametamida, fluxapiroxad, fluxofenim, folpet, fomesafeno, fomesafen- sódio, fonofos, foransulfurona, forclorfenuron, formaldeído, formetanato, cloridrato de formetanato, formotiona, formparanato, cloridrato de formparanato, fosamina, fosamina-amônio, fosetila, fosetil-alumínio, fosmetilan, fospirato, fostiazato, fostietan, frontalina, fuberidazol, fucaojing, fucaomi, funai-hecaoling, fufentioureia, furalano, furalaxila, furametrina, furametpir, furatiocarbe, furcarbanila, furconazol, furconazol-cis, furetrina, furfural, furilazol, furmeciclox, furofanato, furiloxifeno, gamma-cihalotrina, gamma-HC, genit, ácido gibberélico, gibberellins, gliftor, glufosinato, glufosinato-amônio, glufosinato-P, glufosinato-P-amônio, glufosinato-P-sódio, gliodina, glioxima, glifosato, glifosato-diamônio, glifosato-dimetilamônio, glifosato-isopropilamônio, glifosato-monoamônio, glifosato-potássio, glifosato-sesquisódio, glifosato-trimésio, glifosina, gossiplure, grandlure, griseofulvina, guazatina, acetato de guazatina, halacrinato, halauxifeno, halauxifeno- metila, halfenprox, halofenozida, halosafeno, halossulfurona, halossulfurona-metila, haloxidina, haloxifop, haloxifop-etotila, haloxifop- metila, haloxifop-P, haloxifop-P-etotila, haloxifop-P-metila, haloxifop- sódio, HC, hemel, hempa, HEOD, heptaclor, heptaflutrina, heptenofos, heptopargil, herbimicina, heterofos, hexacloroacetona, hexaclorobenzeno, hexaclorobutadieno, hexaclorofeno, hexaconazol, hexaflumuron, hexaflurato, hexalure, hexamida, hexazinona, hexiltiofos, hexitiazox, HHDN, holosulf, huancaiwo, huangcaoling, huanjunzuo, hidrametilnon, hidrargafen, lima hidratada, hidrogênio cianeto, hidropreno, himexazol, hiquincarbe, IAA, IBA, icaridina, imazalil, imazalil nitrato, imazalil sulfato, imazametabenz, imazametabenz-metila, imazamox, imazamox-amônio, imazapic, imazapic-amônio, imazapir, imazapir-isopropilamônio, imazaquina, imazaquin-amônio, imazaquin- metila, imazaquin-sódio, imazetapir, imazetapir-amônio, imazosulfuron, imibenconazol, imiciafos, imidacloprida, imidaclotiz, iminoctadina, triacetato de iminoctadina, trialbesilato de iminoctadina, imiprotrina, inabenfida, indanofan, indaziflam, indoxacarbe, inezina, inpirfluxam, iodobonil, iodocarbe, iodometano, iodossulfurona, iodossulfurona- metila, iodosulfuron-metil-sódio, iofensulfuron, iofensulfuron-sódio, ioxinila, octanoato de ioxinila, ioxinil-lítio, ioxinil-sódio, ipazina, ipconazol, ipfencarbazona, ipfentrifluconazol, ipflufenoquina, iprobenfos, iprodiona, iprovalicarbe, iprimidam, ipsdienol, ipsenol, IPSP, isamidofos, isazofos, isobenzan, isocarbamida, isocarbofos, isocil, isodrina, isofenfos, isofenfos-metila, isofetamida, isoflucipram, isolan, isometiozina, isonoruron, isopolinato, isoprocarbe, isopropalina, isoprotiolano, isoproturon, isopirazam, isopirimol, isotioato, isotianil, isouron, isovalediona, isoxaben, isoxaclortol, isoxadifeno, isoxadifen- etila, isoxaflutol, isoxapirifop, isoxation, ivermectina, izopanfos, japonilure, japotrinas, jasmolina I, jasmolina II, ácido jasmônico, jiahuangcongzong, jiajizengxiaolina, jiaxiangjunzhi, jiecaowan, jiecaoxi, jodfenfos, hormônio juvenil I, hormônio juvenil II, hormônio juvenil III, cadetrina, kappa-bifentrina, kappa-teflutrina, carbutilato, caretazan, caretazan-potássio, casugamicina, cloridrato de casugamicina, kejunlina, celevan, cetospiradox, cetospiradox-potássio, cinetina, cinopreno, cresoxim-metila, cuicaóxi, lactofen, lambda-cihalotrina, lancotriona, latilure, arsenato de chumbo, lenacil, lepimectina, leptofos, lindano, lineatina, linuron, lirinfos, litlure, looplure, lufenuron, lvdingjunzhi, lvxiancaolina, litidation, MAA, malation, maleic hidrazida, malonoben, maltodextrina, MAMA, mancopper, mancozeb, mandestrobina, mandipropamid, maneb, matrina, mazidox, MCPA, MCPA-2-etil-hexila, MCPA-butotila, MCPA-butila, MCPA-dimetilamônio, MCPA-diolamina, MCPA-etila, MCPA-isobutila, MCPA-isoctila, MCPA- isopropila, MCPA-metila, MCPA-olamina, MCPA-potássio, MCPA- sódio, MCPA-tioetila, MCPA-trolamina, MCPB, MCPB-etila, MCPB- metila, MCPB-sódio, mebenil, mecarbam, mecarbinzida, mecarfon, mecoprop, mecoprop-2-etil-hexila, mecoprop-dimetilamônio, mecoprop- diolamina, mecoprop-etadila, mecoprop-isoctila, mecoprop-metila, mecoprop-P, mecoprop-P-2-etil-hexila, mecoprop-P-dimetilamônio, mecoprop-P-isobutila, mecoprop-potássio, mecoprop-P-potássio, mecoprop-sódio, mecoprop-trolamina, medimeform, medinoterb, acetato de medinoterb, medlure, mefenacet, mefenpir, mefenpir-dietila, mefentrifluconazol, mefluidida, mefluidida-diolamina, mefluidida- potássio, ácido megatomoico, menazon, mepanipirim, meperflutrina, mefenato, mefosfolan, mepiquat, cloreto de mepiquat, mepiquat pentaborato, mepronil, meptildinocap, cloreto de mercúrio, óxido de mercúrio, cloreto de mercúrio, merfos, mesoprazina, mesossulfurona, mesossulfurona-metila, mesotriona, mesulfeno, mesulfenfos, metcamifen, metaflumizona, metalaxila, metalaxil-M, metaldeído, metam, metam-amônio, metamifop, metamitron, metam-potássio, metam-sódio, metazaclor, metazosulfurona, metazoxolona, metconazol, metepa, metflurazon, metabenztiazuron, metacrifos, metalpropalina, metamidofos, metasulfocarbe, metazol, metfuroxam, metidationa, metiobencarbe, metiocarbe, metiopirisulfurona, metiotepa, metiozolina, metiuron, metocrotofos, metometon, metomila, metopreno, metoprotrina, metoquin-butila, metotrina, metoxiclor, metoxifenozida, metoxifenona, afloat de metila, brometo de metila, eugenol de metila, iodeto de metila, isotiocianato de metila, metilacetofos, metilclorofórmio, metildimron, cloreto de metileno, benzoato de metilmercúrio, diciandiamida de metilmercúrio, pentaclorofenóxido de metilmercúrio, metilneodecanamida, metiram, metobenzuron, metobromuron, metoflutrina, metolaclor, metolcarbe, metominostrobina, metosulam, metoxadiazona, metoxuron, metrafenona, metribuzina, metsulfovax, metsulfuron, metsulfuron-metila, metiltetraprol, mevinfos, mexacarbato, mieshuan, milbemectina, milbemicin oxime, milneb, mipafox, mirex, MNAF, mogucun, molinato, molosultap, monfluorotrina, monalida, monisouron, ácido monocloroacético, monocrotofos, monolinurona, monossulfurona, monossulfurona-éster, monuron, monuron TCA, morfanquat, cloreto de morfanquat, moroxidina, cloridrato de moroxidina, morfotiona, morzida, moxidectina, MSMA, muscalure, miclobutanila, miclozolina, N-(etilmercuri)-p-toluenossulfonanilida, nabam, naftalofos, naled, naftaleno, naftalenoacetamida, anidrido naftálico, ácidos naftoxiacético, naproanilida, napropamida, napropamida-M, naptalam, naptalam-sódio, natamicina, neburon, niclosamida, niclosamida-olamina, nicossulfurona, nicotina, nifluridida, nipiraclofeno, nitenpiram, nitiazina, nitralina, nitrapirina, nitrilacarbe, nitrofeno, nitrofluorfeno, nitrostireno, nitrotal-isopropila, norbormida, norflurazon, nornicotina, noruron, novaluron, noviflumuron, nuarimol, OC, octaclorodipropil éter, octilinona, ofurace, ometoato, orbencarbe, orfralure, orto-diclorobenzeno, ortosulfamuron, orictalure, orisastrobina, orizalina, ostol, ostramona, oxabetrinila, oxadiargila, oxadiazon, oxadixila, oxamato, oxamila, oxapirazon, oxapirazon-dimolamina, oxapirazon-sódio, oxasulfuron, oxatiapiprolina, oxaziclomefona, oxazosulfila, oxina-cobre, ácido oxolínico, oxpoconazol, oxpoconazol fumarato, oxicarboxina, oxidemeton-metila, oxideprofos, oxidisulfoton, oxifluorfeno, oximatrina, oxitetraciclina, cloridrato de oxitetraciclina, paclobutrazol, paicongding, para-diclorobenzeno, parafluron, paraquat, dicloreto de paraquat, dimetilsulfato de paraquat, parationa, parationa- metila, parinol, pebulato, pefurazoato, ácido pelargônico, penconazol, pencicuron, pendimetalina, penflufen, penfluron, penoxsulam, pentaclorofenol, pentaclorofenil laurato, pentanoclor, pentiopirad, pentmetrina, pentoxazona, perfluidona, permetrina, petoxamida, fenamacril, óxido de fenazina, fenisofam, fencapton, femedifam, femedifam-etila, fenobenzuron, fenotrina, fenpróxido, fentoato, fenilmercuriureia, acetato de fenilmercúrio, cloreto de fenilmercúrio, derivado de fenilmercúrio pirocatecol, nitrato de fenilmercúrio, salicilato de fenilmercúrio, forato, fosacetim, fosalona, fosdifeno, fosfolan, fosfolan-metila, fosglicina, fosmet, fosniclor, fosfamidon, fosfina, fosfocarbe, fósforo, fostina, foxim, foxim-metila, ftalida, picarbutrazox, picloram, picloram-2-etil-hexila, picloram-isoctila, picloram-metila, picloram-olamina, picloram-potássio, picloram-trietilamônio, picloram- tris(2-hidroxipropil)amônio, picolinafen, picoxistrobina, pindona, pindone-sódio, pinoxaden, piperalina, butóxido de piperonila, cicloneno de piperonila, piperofos, piproctanila, brometo de piproctanila, piprotal, pirimetafos, pirimicarbe, pirimioxifos, pirimifos-etila, pirimifos-metila, plifenato, policarbamato, polioxins, polioxorim, polioxorim-zinco, politialan, arseneto de potássio, azida de potássio, cianato de potássio, gibberellato de potássio, naftenato de potássio, polissulfeto de potássio, tiocianato de potássio, α-naftalenoacetato de potássio, pp'-DDT, pralletrina, precoceno I, precoceno II, precoceno III, pretilaclor, primidofos, primissulfurona, primissulfurona-metila, probenazol, procloraz, procloraz-manganês, proclonol, prociazina, procimidona, prodiamina, profenofos, profluazol, profluralina, proflutrina, profoxidim, proglinazina, proglinazina-etila, pró-hexadiona, pró-hexadiona-cálcio, pró-hidrojasmon, promacila, promecarbe, prometon, prometrina, promurit, propaclor, propamidina, di-cloridrato de propamidina, propamocarbe, cloridrato de propamocarbe, propanila, propafos, propaquizafop, propargite, propartrina, propazina, propetamfos, propham, propiconazol, propineb, propisoclor, propoxur, propoxicarbazona, propoxicarbazona-sódio, propil isoma, propirisulfurona, propizamida, proquinazid, prosuler, prosulfalina, prosulfocarbe, prosulfuron, protidation, protiocarbe, cloridrato de protiocarbe, protioconazol, protiofos, protoato, protrifenbute, proxan, proxan-sódio, prinaclor, pidanon, pidiflumetofeno, piflubumida, pimetrozina, piracarbolida, piraclofos, piraclonil, piraclostrobina, piraflufeno, piraflufen-etila, pirafluprol, piramat, pirametostrobina, piraoxistrobina, pirapropoina, pirasulfotol, piraziflumid, pirazolinato, pirazofos, pirazossulfurona, pirazossulfuron-etila, pirazotion, pirazoxifeno, piresmetrina, piretrina I, piretrina II, piretrinas, piribambenz-isopropila, piribambenz-propila, piribencarbe, piribenzoxim, piributicarbe, piriclor, piridabeno, piridaclometila, piridafol, piridalila, piridafentiona, piridato, piridinitril, pirifenox, pirifluquinazon, piriftalida, pirimetanil, pirimidifeno, piriminobac, piriminobac-metila, piriminostrobina, pirimisulfan, pirimitato, pirinuron, piriofenona, piriprol, piripropanol, piriproxifeno, pirisoxazol, piritiobac, piritiobac-sódio, pirolan, piroquilon, piroxasulfona, piroxsulam, piroxiclor, piroxifur, quassia, quinacetol, quinacetol sulfato, quinalfos, quinalfos-metila, quinazamida, quinclorac, quinconazol, quinmerac, quinoclamina, quinofumelina, quinonamida, quinotiona, quinoxifeno, quintiofos, quintozeno, quizalofop, quizalofop-etila, quizalofop-P, quizalofop-P- etila, quizalofop-P-tefurila, quwenzhi, quiingding, rabenzazol, rafoxanida, rebemida, rescalure, resmetrina, rodetanil, rodojaponina-III, ribavirina, rimsulfuron, rotenona, riania, saflufenacil, saijunmao, saisentong, salicilanilida, sanguinarina, santonina, scradan, scilliroside, sebutilazina, secbumeton, sedaxano, selamectina, semiamitraz, cloreto de semiamitraz, sesamex, sesamolina, setoxidim, shuangjiaancaolina, siduron, siglure, silafluofen, silatrano, silica gel, siltiofam, simazina, simeconazol, simeton, simetrina, sintofen, SMA, S-metolaclor, arsenita de sódio, azida de sódio, clorato de sódio, fluoreto de sódio, fluoroacetato de sódio, hexafluorossilicato de sódio, naftenato de sódio, ortofenilfenóxido de sódio, pentaclorofenóxido de sódio, polissulfeto de sódio, tiocianato de sódio, α-naftalenoacetato de sódio, sofamida, espinetoram, espinosad, espirodiclofeno, espiromesifeno, espiropidiona, espirotetramat, espiroxamina, estreptomicina, sesquisulfato de estreptomicina, estricnina, sulcatol, sulcofuron, sulcofuron-sódio, sulcotriona, sulfallato, sulfentrazona, sulfiram, sulfluramida, sulfometuron, sulfometuron-metila, sulfossulfurona, sulfotep, sulfoxaflor, sulfóxido, sulfoxima, enxofre, ácido sulfúrico, fluoreto de sulfurila, sulglicapina, sulprofos, sultropen, swep, tau- fluvalinato, tavron, tazincarbe, TCA, TCA-amônio, TCA-cálcio, TCA- etadila, TCA-magnésio, TCA-sódio, TDE, tebuconazol, tebufenozida, tebufenpirad, tebufloquina, tebupirinfos, tebutam, tebutiuron, tecloftalam, tecnazeno, tecoram, teflubenzuron, teflutrina, tefuriltriona, tembotriona, temefos, tepa, TEPP, tepraloxidim, teralletrina, terbacil, terbucarbe, terbuclor, terbufos, terbumeton, terbutilazina, terbutrina, tetciclacis, tetracloroetano, tetraclorvinfos, tetraconazol, tetradifon, tetrafluron, tetrametrina, tetrametilflutrina, tetramina, tetranactina, tetraniliprol, tetrasul, sulfato de tálio, tenilclor, teta-cipermetrina, tiabendazol, tiacloprida, tiadifluor, tiametoxam, tiapronil, tiazafluron, tiazopir, ticrofos, ticiofen, tidiazimina, tidiazuron, tiencarbazona, tiencarbazona-metila, tifensulfuron, tifensulfuron-metila, tifluzamida, tiobencarbe, tiocarboxima, tioclorfenfim, tiociclam, cloridrato de tiociclam, oxalato de tiociclam, tiodiazol-cobre, tiodicarbe, tiofanox, tiofluoximato, tiohempa, tiomersal, tiometon, tionazina, tiofanato, tiofanato-metila, tioquinox, tiosemicarbazida, tiosultap, tiosultap- diamônio, tiosultap-disódio, tiosultap-monosódio, tiotepa, tiram, turingiensina, tiadinil, tiafenacil, tiaojiean, tiocarbazil, tioclorim, tioxazafeno, tioximida, tirpato, tolclofos-metila, tolfenpirad, tolprocarbe, tolpiralato, tolilfluanid, tolilmercúrio acetato, topramezona, tralkoxidim, tralocitrina, tralometrina, tralopiril, transflutrina, transpermetrina, tretamina, triacontanol, triadimefon, triadimenol, triafamona, tri-allato, triamifos, triapentenol, triarateno, triarimol, triasulfuron, triazamato, triazbutil, triaziflam, triazofos, triazóxido, tribenuron, tribenuron-metila, tribufos, óxido de tributilestanho, tricamba, triclamida, triclorfon, triclormetafos-3, tricloronat, triclopir, triclopir-butotila, triclopir-etila, triclopiricarbe, triclopir-trietilamônio, triciclazol, tridemorf, tridiphano, trietazina, trifenmorf, trifenofos, trifloxistrobina, trifloxisulfuron, trifloxisulfuron-sódio, trifludimoxazina, triflumezopirim, triflumizol, triflumuron, trifluralina, triflussulfurona, triflussulfurona-metila, trifop, trifop-metila, trifopsima, triforina, tri-hidroxitriazina, trimedlure, trimetacarbe, trimeturon, trinexapac, trinexapac-etila, tripreno, tripropindan, triptolide, tritac, triticonazol, tritosulfuron, trunc-call, ticlopirazoflor, uniconazol, uniconazol-P, urbacide, uredepa, valerato, validamicina, valifenalato, valona, vamidotiona, vangard, vaniliprol, vernolato, vinclozolina, warfarina, warfarina-potássio, warfarina-sódio, xiaocongliulina, xinjunan, xiwojunan, XMC, xilaclor, xilenols, xililcarbe, iishijing, zarilamida, zeatina, zengxiaoan, zeta-cipermetrina, naftenato de zinco, fesfeto de zinco, tiazol de zinco, zineb, ziram, zolaprofos, zoxamida, zuomihuanglong, α-cloro-hidrina, α-ecdisona, α-multistriatina, e ácido a-naftalenoacético. Para maiores informações consultar o "COMPENDIUM OF PESTICIDE COMMON NAMES" localizado em http://www.alanwood.net/pesticides/index.html. Também consultar "THE PESTICIDE MANUAL" 15a Edição, editado por C D S Tomlin, copiright 2009 por British Crop Production Council, ou suas edições anteriores, ou mais recentes.
[00153] Em outra modalidade, moléculas de Fórmula Um e/ou Fórmula Dois podem também ser usadas em combinação (tal como em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com um ou mais biopesticidas. O termo "biopesticida" é usado para agentes de controle de peste biológica microbiana que são aplicados de maneira similar aos pesticidas químicos. Comumente estes são bacterianos, porém existem outros exemplos de agentes de controle fúngicos, incluindo Trichoderma spp. e Ampelomyces quisqualis (um agente de controle para molfo pulverulento da uva). Bacillus subtilis são usados para controlar os patógenos de planta. Ervas daninhas e roedores também foram controlados com agentes microbianos. Um exemplo de inseticida bem conhecido é Bacillus thuringiensis, uma doença bacteriana de Lepidópteros, Coleópteros, e Dípteros. Por que ele tem pouco efeito sobre outros organismos, ele é considerado mais ecologicamente amigável do que pesticidas sintéticos. Inseticidas biológicos incluem produtos com base em: fungos entomopatogênicos (por exemplo, Metarhizium anisopliae); nematodas entomopatogênicos (por exemplo, Steinernema feltiae); e virus entomopatogênicos (por exemplo, granulovírus por Cydia pomonella).
[00154] Outros exemplos de organismos entomopatogênicos incluem, porém não estão limitados à, baculovírus, bactérias e outros organismos procarióticos, fungos, protozoários e Microsproridia. Inseticidas biologicamente derivados incluem, porém não estão limitados à rotenona, veratridina, bem como toxinas microbianas; variedades de planta tolerantes ou resistentes a inseto; e organismos modificados por tecnologia de DNA recombinante para produzir inseticidas ou ara transmitir uma propriedade resistente a inseto ao organismo geneticamente modificado. Em uma modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas com um ou mais biopesticidas na área de tratamento de semente e alterações de solo. O Manual of Biocontrol Agents fornece uma revisão dos produtos inseticidas biológicos disoníveis (e outro controle com base na biologia). Copping L.G. (ed.) (2004). The Manual of Biocontrol Agents (anteriormente, o Biopesticide Manual) 3a Edição. British Crop Production Council (BCPC), Farnham, Surrey Reino Unido.
[00155] Em outra modalidade, as possíveis combinações acima podem ser usadas em uma ampla variedade de relações de peso. Por exemplo, uma mistura de dois componentes, a relação de peso de uma molécula de Fórmula Um e/ou Fórmula Dois para outro composto, pode ser de cerca de 100:1 a cerca de 1:100; em outro exemplo, a relação de peso pode ser de cerca de 50:1 a cerca de 1:50; em outro exemplo, a relação de peso pode ser de cerca de 20:1 a cerca de 1:20; em outro exemplo, a relação de peso pode ser de cerca de 10:1 a cerca de 1:10; em outro exemplo, a relação de peso pode ser de cerca de 5:1 a 1:5; em outro exemplo, a relação de peso pode ser de cerca de 3:1 a cerca de 1:3; e em um exemplo final, a relação de peso pode ser de cerca de 1:1. Entretanto, preferivalmente, relações de peso menores do que cerca de 10:1 a cerca de 1:10 são preferidas. Algumas vezes, é também preferível usar um mistura de três ou quatro componentes compreendendo uma ou mais moléculas de Fórmula Um e/ou Fórmula Dois e um ou mais compostos das possíveis combinações acima.
[00156] Um pesticida é raramente adequado para aplicação em sua forma pura. É geralmente necessário adicionar outras substâncias, de modo que o pesticida possa ser usado na concentração requerida e em uma forma apropriada, permitindo facilidade de aplicação, manipulação, transorte, armazenagem, e atividade pesticida máxima. Desse modo, os pesticidas podem ser formulados em, por exemplo, iscas, emulsões concentradas, pós, concentrados emulsificáveis, fumigantes, géis, grânulos, microencapsulações, tratamentos de semente, concentrados de suspensão, suspoemulsões, comprimidos, líquidos solúveis em água, grânulos dispersos em água ou fluíveis secos, pós umectáveis, e soluções de volume ultra baixo. Para outra informação sobre os tipos veja "Catalogue of Pesticide Formulation Types and International Coding System" Technical Monograph n°2, 5a Edição por CropLife International (2002).
[00157] Pesticidas são aplicados mais frequentemente como suspensões aquosas ou emulsões preparadas de formulações concentradas de tais pesticidas. Tais formulações solúveis em água, suspensíveis em água, ou emulsificáveis são sólidas, geralmente conhecidas como pós umectáveis, ou grânulos dispersíveis em água, ou líquidos usualmente conhecidos como concentrados emulsificáveis, ou suspensões aquosas. Pós umectáveis, que podem ser compactados para formar grânulos dispersíveis em água, compreendem uma mistura íntima do pesticida, um veículo e tensoativos. A concentração do pesticida é geralmente de cerca de 10% a cerca de 90% por peso. O veículo é geralmente selecionado entre as argilas de atapulgita, as argilas de montmorilonita, as terra diatomáceas, ou os silicatos purificados. Tensoativos eficazes, compreendendo de cerca de 0,5% a cerca de 10% do pó umectável, são encontrados entre as ligninas sulfonadas, naftalenossulfonatos condensados, naftalenossulfonatos, alquilbenzenossulfonatos, sulfatos de alquila, e tensoativos não iônicos tais como aduzidos de óxido de etileno de alquil fenóis.
[00158] Os concentrados emulsificáveis de pesticidas compreendem uma concentração conveniente de um pesticida, tal como de cerca de 50 a cerca de 500 gramas por litro de líquido dissolvido em um veículo que é um solvente miscível em água ou uma mistura de solvente orgânico imiscível em água e emulsificantes. Os solventes orgânicos úteis incluem produtos aromáticos, especialmente xilenos e frações de petróleo, especialmente as porções naftalênicas e olefínicas de alta ebulição de petróleo tal como nafta aromático pesado. Outros solventes orgânicos podem também ser usados, tal como os solventes terpênicos incluindo derivados de resina, cetonas alifáticas tal como ciclo- hexanona, e álcoois complexos tal como 2-etoxietanol. Os emulsificantes adequados para concentrados emulsificáveis são selecionado de tensoativos aniônicos e não iônicos convencionais.
[00159] As suspensões aquosas compreendem suspensões de pesticidas insolúveis em água dispersas em um veículo aquoso emu ma concentração na faixa de cerca de 5% a cerca de 50% em peso. As suspensões são preparadas por moagem fina do pesticida e mistura vigorosa dele em um veículo compreendido de água e tensoativos. Os ingredientes, tais como sais inorgânicos e gomas sintéticas ou naturais, podem também ser adicionados, para aumentar a densidade e viscosidade do veículo aquoso. É frequentemente mais eficaz misturar o pesticida ao mesmo tempo preparando a mistura aquosa e homogeneizando-a em um implemento tal como um moinho de areia, um moinho de bola ou homogeneizador do tipo pistão.
[00160] Os pesticidas podem também ser aplicados como composições granulares que são particularmente úteis para aplicação ao solo. As composições granulares geralmente contêm cerca de 0,5% a cerca de 10% por peso do pesticida, dispersos em um veículo que compreendem argila ou uma substância similar. Tais composições são geralmente preparados dissolvendo o pesticida em um solvente adequado e aplicando-o a um veículo granular que foi pré-formado para o tamanho de partícula apropriado, na faixa de cerca de 0,5 a cerca de 3 mm. Tais composições podem também ser formuladas preparando uma massa ou pasta do veículo e composto e esmagando e secando para obter o tamanho de partícula granular desejado.
[00161] Pós contendo um pesticida são preparados misturando intimamente o pesticida em forma de pó com um veículo agrícola em pó adequado, tal como argila de caulim, rocha vulcânica moída, e similares. Pós podem adequadamente conter cerca de 1% a cerca de 10% do pesticida. Eles podem ser aplicados como uma adubagem de semente ou uma aplicação à folhagem com uma máquina sopradora de pó.
[00162] É igualmente prático aplicar um pesticida na forma de uma solução em um solvente orgânico apropriado, geralmente óleo de petróleo, tal como os óleos em spray, que são amplamente usados na química agrícola.
[00163] Pesticidas podem atmbém ser aplicados na forma de uma composição de aerossol. Em tais composições, o pesticida é dissolvido ou disperso em um veículo, que é uma mistura propelente de geração de pressão. A composição de aerossol é embalada em um recipiente do qual a mistura é aplicada através de uma válvula de atomização.
[00164] Iscas de pesticida são formadas quando o pesticida é misturado com comid ou um atrativo ou ambos. Quando as pestes comem a isca elas também consumem o pesticida. As iscas podem adotar a forma de grânulos, géis, pós fluíveis, líquidos ou ambos. Elas podem ser usadas em abrigos de peste.
[00165] Fumegantes são pesticidas que têm uma pressão de vapor relativamente e, consequentemente, podem existir como um gás em concentrações suficientes para matar as pestes em um solo ou espaços fechados. A toxicidade do fumegante é proporcional a sua concentração e ao tempo de exposição. Eles são caracterizados pela boa capacidade de difusão e agem penentrando no sistema respiratória da peste ou sendo absorvido através da cuticula da peste. Fumegantes são aplicados para controlar as pestes de produto armazenado sob folhas à prova de gás, em salas lacradas a gás ou edifícios ou câmaras especiais.
[00166] Pesticidas podem ser microencapsulados suspendendo as gotículas ou partículas de pesticida em polímeros plásticos de vários tipos. Alterando a química do polímero ou mudando do fatores no processamento, as microcápsulas podem ser formadas de vários tamanhos, solubilidade, espessura da parede e graus de penetrabilidade. Estes fatores controlam a velocidade com a qual o ingrediente ativo dentro é liberado, que por sua vez, afetam o desepempenho residual, velocidade de ação, e odor do produto.
[00167] Os concentrados de solução oleosa são feitos dissolvendo o pesticida em um solvente que manterá o pesticida na solução. Soluções oleosas de um pesticida geralmente fornecem redução e morte mais rápida de pestes do que outras formulações devido aos próprios solventes terem ação pesticidal e a dissolução do revestimento ceroso do tegumento aumentando a velocidade de captação do pesticida. Outras vantagens das soluções oleosas incluem melhor estabilidade de armazenagem, melhor penetração de fendas e melhor adesão à superficies gordurosas.
[00168] Outra modalidade é uma emulsão óleo-em-água, em que a emulsão compreende glóbulos oleosos que são cada quais fornecidos com um revestimento cristalino líquido lamelar e são disperses emu ma fase aquosa, em que cada glóbulo oleoso pelo menos um composto que é agriculturamente ativo, e é individualmente revestido com uma camada monolamelar ou oligolamelar compreendendo: (1) pelo menos um agente tensoativo lipofílico não iônico, (2) pelo menos um agente tensoativo hidrofílico não iônico e (3) pelo menos um agente tensoativo iônico, em que os glóbulos têm um diâmetro de partícula médio menor do que 800 nanômetros. Outra informação na modalidade é descrita na Publicação de Pedido de Patente dos Estados Unidos 2007/0027034 A1 publicada em 1 de Fevereiro de 2007, tendo o Número de série de Pedido de Patente 11/495.228. Para facilidade de uso, esta modalidade será referida como "OIWE".
[00169] Para outra informação consultar "Insect Pest Management" 2a Edição por D. Dent, copyright CAB International (2000). Além disso, para maior informação consultar "Handbook of Pest Control - The Behavior, Life History, and Control of Household Pests" por Arnold Mallis, 9a Edição, copyright 2004 por GIE Media Inc.
[00170] Geralmente, quando as moléculas descritas na Fórmula Um são usadas em uma formulação, tal formulação pode também conter outros componentes. Estes componentes incluem, porém não são limitados a, (esta é uma lista não exaustiva e não mutuamente exclusiva) umectantes, espalhadores, espessantes, penetrantes, tampões, agentes de sequenciamento, agentes de redução de impulso, agentes de compatibilidade, agentes antiespuma, agentes de limpeza, e emulsificantes. Alguns componentes são descritos imediatamente.
[00171] Um agente umectante é uma substância que quando adicionada a um líquido aumenta o poder de espalhamento e penetração do líquido reduzindo-se a tensão interfacial entre o líquido e a superfície sobre a qual se espalha. Os agentes umectantes são usados são usados para duas funções principais em formulações agroquímicas: durante processamento e fabricação para aumentar a taxa de umidade de pós em água para fazer os concentrados para líquidos solúveis ou concentrados de suspensão; e durante a mistura de um produto com água em um tanque de pulverização para reduzir o tempo de umidade dos pós umectáveis e para melhorar a penetração da água em grânulos dispersíveis em água. Os exemplos de agentes umectantes usados em pó umectável, concentrado de suspensão, e formulações de grânulo dispersíveis em água são: sulfato de laurila de sódio; sulfossuccinato de dioctil de sópdio; etoxilatos de fenol de alquila; e etoxilatos de álcool alifáticos.
[00172] Um agente de dispersão é uma substância que é absorvida sobre a superfície de partículas e ajuda a presevar o estado de dispersão das partículas e previne-as de reagrupamento. Os agentes de dispersão são adicionados a formulações agroquímicas para facilitar a dispersão e suspensão durante a fabricação, e assegurar que as partículas redispersem em água em um tanque de vaporização. Eles são amplamente usados em pós umectáveis, concentrados de suspensão e grânulos dispersíveis em água. Os tensoativos que são usados como agentes dispersantes têm a capacidade serem absorvidos fortemente sobre uma superfície e fornecem uma barreira carregada ou estérica para reagregação de partículas. Os tensoativos mais comumente usados tensoativos são aniônico, non-iônico, ou misturas dos dois tipos. Para as formulações de pó umectável, os agentes de dispersão mais comuns são lignossulfonates de sódio. Para concentrados de suspensão, absorção e estabilização muito boas são obtidas usando polieletrólitos, tais como condensados de formaldeído de sulfonate de naftaleno de sódio. Os ésteres de fosfato de etoxilato de tristirilfenol são também usados. Os não iônicos tais como condensados de óxido de alquilariletileno e copolímeros de bloqueio de EO-PO são às vezes combinados com aniônicos como agentes de dispersão para concentrados de suspensão. E manos recentes, novos tipos de tensoativos poliméricos de peso molecula muito alto foram desenvolvidos como agentes de dispersão. Estes têm "estruturas" hidrofóbicas muito longas e um grande número de cadeias de óxido de etileno que formam o ‘dente’ de um tensoativo ‘pente’. Estes polímeros de alto peso molecular podem fornecer estabilidade de longo prazo muito boa a concentrados de suspensão, porque as estruturas hidrofóbicas têm muitos pontos de ancoragem nas superficies de partícula. Os exemplos de agentes de dispersão usados em formulações agroquímicas são: lignossulfonatos de sódio; condensados de formaldeído de sulfonate de naftaleno de sódio; éteres de fosfato de etoxilato de ésteres de fosfato de etoxilato de tristirilfenol; etoxilatos de álcool alifáticos; etoxilatos de alquila; polímeros de bloqueio de EO-PO; e copolímeros de enxerto.
[00173] Um agente emulsificante é uma substância que estabiliza uma suspensão de gotículas de uma fase líquida em outra fase líquida. Sem o agente emulsificante, os dois líquidos separariam-se em duas fases líquidas imiscíveis. As misturas emulsificantes mais comumentes usadas contêm álcool alquilfenólico ou alifático com doze ou mais unidades de óxido de etileno e o sal de cálcio solúvel em óleo de ácido dodecilbenzenossulfônico. Uma faixa de valores de equilíbrio hidrófilo- lipofílico ("HLB") de 8 a 18 normalmente fornecerá boas emulsões estáveis. A estabilidade de emulsão pode ás vezes ser melhorada pela adição de uma pequena quantidade de um tensoativo de copolímero de bloqueio de EO-PO.
[00174] Um agente de solublização é um tensoativo que formará micelas em água em concentrações acima da concentração de micela crítica. As micelas são em seguida capazes de dissolver ou solubilizar os materiais insolúveis em água dentro da parte hidrofóbica da da micela. Os tipos de tensoativos geralmente usados para solubilização são materiais não iônicos, mono-oleatos de sorbitano, etoxilatos de mono-oleato de sorbitano, e ésteres de oleato de metila.
[00175] Os tensoativos são às vezes usados, sozinhos ou com outros aditivos tais como óleos minerais ou vegetais como adjuvantes para misturas de tanque de vaporização para melhorar o desempenho biológico do pesticida no alvo. Os tipos de tensoativos usados para biorrealce dependem geralmente da natureza e modo de ação do pesticida. Entretanto, eles são frequentemente não iônicos tais como: etoxilatos de alquila; etoxilatos de álcool alifáticos lineares; etoxilatos de amina alifáticos.
[00176] Um veículo ou diluente emu ma formulação agrícola é um material adicionado ao pesticida para fornecer um produto da força requerida. Os veículos são geralmente materiais com alta capacidade de absorção, ao mesmo tempo em que os diluentes são geralmente materiais com baixa capacidade de absorção. Os veículos e diluentes são usados na formulção de pós, pós umectáveis, grânulos e grânulos dispersíveis em água.
[00177] Os solventes orgânicos são usados principalmente na formulação de concentrados emulsificáveis, emulsões de óleo em água, suspoemulsões, e formulações de volume ultrabaixo, e, até um nível menor, formulações granulares. Às vezes, as misturas de solventes são usados. Os primeiros grupos principais de solventes são óleos parafínicos alifáticos tais como querosene ou parafinas refinadas. O segundo grupo principal (e o mais comum) compreende os solventes aromáticos tais como frações de peso molecular mais alto de solventes aromáticos de C9 e C10. Os hidrocarbonetos clorados são úteis como cossolventes para prevenir a cristalização de pesticidas quando a formulação é emulsificada em água. Os álcoois são às vezes usados como cossolventes para aumentar o poder do solvente. Outros solventes podem incluir óleos vegetais, óleos de semente, e ésteres de óleos de semente e vegetais.
[00178] Os espessantes ou agentes gelificantes são usados principalmente na formulação de concentrados de suspensão, emulsões e suspoemulsões para modificar a reologia ou propriedades de fluxo do líquido e prevenir a separação e assentamento das partículas ou gotículas dispersas. Os agentes espessantes, gelificantes, e antiassentamento geralmente incluem-se em duas categorias, isto é, particularidades insolúveis em água e polímeros olúveis em água. É possível produzir formulações de concentrado de suspensão usando argilas e sílicas. Os exemplos destes tipos de materiais, incluem, porém não são limitados a, montmorillonita, bentonita, silicato de alumínio de magnésio, e attapulgita. Os polissacarídeos solúveis em água foram usados como agentes de gelificação de espessante durante muitos antes. Os tipos de polissacarídeos mais comumente usados são extratos naturais de sementes e algas marinhas ou são derivados sintéticos de celulose.
[00179] Os exemplos destes tipos de materiais incluem, porém não são limitados a, goma guar; goma de alforraba; carragenina; alginatos; metil celulose; carboximetil celulose de sódio (SCMC); hidroxietil celulose (HEC). Outros tipos de angentes antiassentamento são com base em amidos modificados, poliacrilatos, álcool polivinílico e óxido de polietileno. Outro agente bom antiassentamento é goma xantana.
[00180] Os micro-organismos podem causar deterioração de produtos formulados. Entretanto, os agentes de preservação são usados para eliminar ou reduzir seu efeito. Os exemplos de tais agentes incluem, porém não são limitados a: ácido propiônico e seu sal de sódio; ácido ascórbico e seus sais de potássio ou sódio; ácido benzoico e seu sal de sódio; sal de sódio de ácido p-hidroxibenzoico; p-hidroxibenzoato de metila; e 1,2-benzisotiazolin-3-ona (BIT).
[00181] A presença de tensoativos frequentemente faz as formulações baseadas em água espumar durante as operações de mistura em produção e em aplicação por meio de um tanque de vaporização. Para reduzir a tendência a espumar, os agentes antiespuma são frequentemente adicionados durante o estágio de produção ou antes do carregamento em garrafas. Geralmente, há dois tipos de agentes antiespuma, isto é, silicones e não silicones. Os silicones são geralmente emulsões aquosas de polissiloxilano de dimetila, ao mesmo tempo em que os agentes antiespumas não silicones são óleos insolúveis em água, tais como octanol e nonanol, ou sílica. Em ambos os casos, a função do agente antiespuma é deslocar o tensoativo da interface ar-água.
[00182] Os agentes "verdes" (por exemplo, adjuvantes, tensoativos, solventes) podem reduzir a pegada ambiental global de formulações de proteção de colheita. Os agentes verdes são biodegradáveis e geralmente derivados de fontes naturais e/ou sustentáveis, por exemplo, fontes de planta e animal. Os exemplos específicos são: óleos vegetais, óleos de semente, e ésteres dos mesmos, além de poliglicosídeos de alquila alcoxilados.
[00183] Para mais informações, veja "Chemistry and Technology of Agrochemical Formulations" editado por D.A. Knowles, direito autoral de 1998 pela Kluwer Academic Publishers. Além disso veja "Insecticides in Agriculture and Environment - Retrospects and Prospects" por A.S. Perry, I. Yamamoto, I. Ishaaya, e R. Perry, direito autoral de 1998 pela Springer-Verlag.
[00184] Em geral, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar, por exemplo, formigas, pulgões, besouros, traças, baratas, grilos, tesourinhas, pulgas, moscas, gafanhotos, cigarrinhas, piolhos, gafanhotos, ácaros, mariposas, nematóides, escalas, Symphylans, cupins, tripes, carrapatos, vespas, e moscas brancas.
[00185] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar as pestes nos Filos Nematoda e/ou Artropoda.
[00186] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar as pestes nos Subfilos Chelicerata, Miriapoda, e/ou Hexapoda.
[00187] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar as pestes nas Classes de Arachnida, Symphyla, e/ou Insecta.
[00188] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Anoplura. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Haematopinus spp., Hoplopleura spp., Linognathus spp., Pediculus spp., e Polyplax spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Haematopinus asini, Haematopinus suis, Linognathus setosus, Linognathus ovillus, Pediculus humanus capitis, Pediculus humanus humanus, e Pthirus pubis.
[00189] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar as pestes na Ordem de Coleópteros. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Acanthoscelides spp., Agriotes spp., Anthonomus spp., Apion spp., Apogonia spp., Aulacophora spp., Bruchus spp., Cerosterna spp., Cerotoma spp., Ceutorhynchus spp., Chaetocnema spp., Colaspis spp., Ctenicera spp., Curculio spp.,Ciclocephala spp., Diabrotica spp., Hypera spp., Ips spp., Lyctus spp., Megascelis spp., Meligethes spp., Otiorhynchus spp., Pantomorus spp., Phyllophaga spp., Phyllotreta spp., Rhizotrogus spp., Rhynchites spp., Rhynchophorus spp., Scolytus spp., Sfenophorus spp., Sitophilus spp., e Tribolium spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Acanthoscelides obtectus, Agrilus planipennis, Anoplophora glabripennis, Anthonomus grandis, Ataenius spretulus, Atomaria linearis, Bothynoderes punctiventris, Bruchus pisorum, Callosobruchus maculatus, Carpophilus hemipterus, Cassida vittata, Cerotoma trifurcata, Ceutorhynchus assimilis, Ceutorhynchus napi, Conoderus scalaris, Conoderus stigmosus, Conotrachelus nenuphar, Cotinis nitida, Crioceris asparagi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptolestes turcicus, Cylindrocopturus adspersus, Deporaus marginatus, Dermestes lardarius, Dermestes maculatus, Epilachna varivestis, Faustinus cubae, Hylobius pales, Hypera postica, Hypothenemus hampei, Lasioderma serricorne, Leptinotarsa decemlineata, Liogenys fuscus, Liogenys suturalis, Lissorhoptrus oryzophilus, Maecolaspis joliveti, Melanotus communis, Meligethes aeneus, Melolontha melolontha, Oberea brevis, Oberea linearis, Oryctes rhinoceros, Oryzaephilus mercator, Oryzaephilus surinamensis, Oulema melanopus, Oulema oryzae, Phyllophaga cuyabana, Popillia japonica, Proetapahanus truncatus, Rhyzopertha dominica,, Sitona lineatus, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum, Tribolium castaneum, Tribolium confusum, Trogoderma variabile, e Zabrus tenebrioides.
[00190] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar as pestes da Ordem de Dermápteros.
[00191] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Blattaria. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Blattella germanica, Blatta orientalis, Parcoblatta pennsylvanica, Periplaneta americana, Periplaneta australasiae, Periplaneta brunnea, Periplaneta fuliginosa, Pycnoscelus surinamensis, e Supella longipalpa.
[00192] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Dípteros. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Aedes spp., Agromyza spp., Anastrepha spp., Anopheles spp., Bactrocera spp., Ceratitis spp., Chrysops spp., Cochliomyia spp., Contarinia spp., Culex spp., Dasineura spp., Delia spp., Drosophila spp., Fannia spp., Hylemyia spp., Liriomyza spp., Musca spp., Phorbia spp., Tabanus spp., e Tipula spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Agromyza frontella, Anastrepha suspensa, Anastrepha ludens, Anastrepha obliqa, Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera invadens, Bactrocera zonata, Ceratitis capitata, Dasineura brassicae, Delia platura, Fannia canicularis, Fannia scalaris, Gasterophilus intestinalis, Gracillia perseae, Haematobia irritans, Hypoderma lineatum, Liriomyza brassicae, Melophagus ovinus, Musca autumnalis, Musca domestica, Oestrus ovis, Oscinella frit, Pegomya betae, Psila rosae, Rhagoletis cerasi, Rhagoletis pomonella, Rhagoletis mendax, Sitodiplosis mosellana, e Stomoxys calcitrans.
[00193] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Hemípteros. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Adelges spp., Aulacaspis spp., Aphrophora spp., Aphis spp., Bemisia spp., Ceroplastes spp., Chionaspis spp., Chrysomphalus spp., Coccus spp., Empoasca spp., Lepidosaphes spp., Lagynotomus spp., Lygus spp., Macrosiphum spp., Nephotettix spp., Nezara spp., Philaenus spp., Phytocoris spp., Piezodorus spp., Planococcus spp., Pseudococcus spp., Rhopalosiphum spp., Saissetia spp., Therioaphis spp., Toumeyella spp., Toxoptera spp., Trialeurodes spp., Triatoma spp. e Unaspis spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Acrosternum hilare, Acyrthosiphon pisum, Aleyrodes proletella, Aleurodicus dispersus, Aleurothrixus floccosus, Amrasca biguttula biguttula, Aonidiella aurantii, Aphis gossypii, Aphis glycines, Aphis pomi, Aulacorthum solani, Bemisia argentifolii, Bemisia tabaci, Blissus leucopterus, Brachycorynella asparagi, Brevennia rehi, Brevicoryne brassicae, Calocoris norvegicus, Ceroplastes rubens, Cimex hemipterus, Cimex lectularius, Dagbertus fasciatus, Dichelops furcatus, Diuraphis noxia, Diaphorina citri, Dysaphis plantaginea, Dysdercus suturellus, Edessa meditabunda, Eriosoma lanigerum, Eurygaster maura, Euschistus heros, Euschistus servus, Helopeltis antonii, Helopeltis theivora, Icerya purchasi, Idioscopus nitidulus, Laodelphax striatellus, Leptocorisa oratorius, Leptocorisa varicornis, Lygus hesperus, Maconellicoccus hirsutus, Macrosiphum euphorbiae, Macrosiphum granarium, Macrosiphum rosae, Macrosteles quadrilineatus, Mahanarva frimbiolata, Metopolophium dirhodum, Mictis longicornis, Myzus persicae, Nephotettix cinctipes, Neurocolpus longirostris, Nezara viridula, Nilaparvata lugens, Parlatoria pergandii, Parlatoria ziziphi, Peregrinus maidis, Phylloxera vitifoliae, Physokermes piceae,, Phytocoris californicus, Phytocoris relativus, Piezodorus guildinii, Poecilocapsus lineatus, Psallus vaccinicola, Pseudacysta perseae, Pseudococcus brevipes, Quadraspidiotus perniciosus, Rhopalosiphum maidis, Rhopalosiphum padi, Saissetia oleae, Scaptocoris castanea, Schizaphis graminum, Sitobion avenae, Sogatella furcifera, Trialeurodes vaporariorum, Trialeurodes abutiloneus, Unaspis yanonensis, e Zulia entrerriana.
[00194] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Himenópteros. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Acromyrmex spp., Atta spp., Camponotus spp., Diprion spp., Formica spp., Monomorium spp., Neodiprion spp., Pogonomyrmex spp., Polistes spp., Solenopsis spp., Vespula spp., e Xylocopa spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Athalia rosae, Atta texana, Iridomyrmex humilis, Monomorium minimum, Monomorium pharaonis, Solenopsis invicta, Solenopsis geminata, Solenopsis molesta, Solenopsis richtery, Solenopsis xyloni, e Tapinoma sessile.
[00195] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Isópteros. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Coptotermes spp., Cornitermes spp., Cryptotermes spp., Heterotermes spp., Kalotermes spp., Incisitermes spp., Macrotermes spp., Marginitermes spp., Microcerotermes spp., Procornitermes spp., Reticulitermes spp., Schedorhinotermes spp., e Zootermopsis spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Coptotermes curvignathus, Coptotermes frenchi, Coptotermes formosanus, Heterotermes aureus, Microtermes obesi, Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermes flavipes, Reticulitermes hageni, Reticulitermes hesperus, Reticulitermes santonensis, Reticulitermes speratus, Reticulitermes tibialis, e Reticulitermes virginicus.
[00196] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Lepidópteros. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Adoxophyes spp., Agrotis spp., Argyrotaenia spp., Cacoecia spp., Caloptilia spp., Chilo spp., Chrysodeixis spp.,Colias spp., Crambus spp., Diaphania spp., Diatraea spp., Earias spp., Ephestia spp., Epimecis spp., Feltia spp., Gortyna spp., Helicoverpa spp., Heliothis spp., Indarbela spp., Lithocolletis spp., Loxagrotis spp., Malacosoma spp., Peridroma spp., Phyllonorycter spp., Pseudaletia spp., Sesamia spp., Spodoptera spp., Synanthedon spp., e Yponomeuta spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Achaea janata, Adoxophyes orana, Agrotis ipsilon, Alabama argillacea, Amorbia cuneana, Amyelois transitella, Anacamptodes defectaria, Anarsia lineatella, Anomis sabulifera, Anticarsia gemmatalis, Archips argyrospila, Archips rosana, Argyrotaenia citrana, Autographa gamma, Bonagota cranaodes, Borbo cinnara, Bucculatrix thurberiella, Capua reticulana, Carposina niponensis, Chlumetia transversa, Choristoneura rosaceana,Cnaphalocrocis medinalis, Conopomorfa cramerella, Cossus cossus, Cydia caryana, Cydia funebrana, Cydia molesta, Cydia nigricana, Cydia pomonella, Darna diducta, Diatraea saccharalis, Diatraea grandiosella, Earias insulana, Earias vittella, Ecdytolopha aurantianum, Elasmopalpus lignosellus, Ephestia cautella, Ephestia elutella, Ephestia kuehniella, Epinotia aporema, Epiphyas postvittana, Erionota thrax, Eupoecilia ambiguella, Euxoa auxiliaris, Grapholita molesta, Hedylepta indicata, Helicoverpa armigera, Helicoverpa zea, Heliothis virescens, Hellula undalis, Keiferia lycopersicella, Leucinodes orbonalis, Leucoptera coffeella, Leucoptera malifoliella, Lobesia botrana, Loxagrotis albicosta, Lymantria dispar, Lyonetia clerkella, Mahasena corbetti, Mamestra brassicae, Maruca testulalis, Metisa plana, Mythimna unipuncta, Neoleucinodes elegantalis, Nymphula depunctalis,Operophtera brumata, Ostrinia nubilalis, Oxydia vesulia, Pandemis cerasana, Pandemis heparana, Papilio demodocus, Pectinophora gossypiella, Peridroma saucia, Perileucoptera coffeella, Ftorimaea operculella, Phyllocnistis citrella, Pieris rapae, Plathypena scabra, Plodia interpunctella, Plutella xylostella, Polychrosis viteana, Prays endocarpa, Prays oleae, Pseudaletia unipuncta, Pseudoplusia includens, Rachiplusia nu, Scirpophaga incertulas, Sesamia inferens, Sesamia nonagrioides, Setora nitens, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera eridania, Thecla basilides, Tineola bisselliella, Trichoplusia ni, Tuta absoluta, Zeuzera coffeae, e Zeuzera pirina.
[00197] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Mallophaga. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Anaticola spp., Bovicola spp., Chelopistes spp., Goniodes spp., Menacanthus spp., e Trichodectes spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Bovicola bovis, Bovicola caprae, Bovicola ovis, Chelopistes meleagridis, Goniodes dissimilis, Goniodes gigas, Menacanthus straminaus, Menopon gallinae, e Trichodectes canis.
[00198] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Ortópteros. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Melanoplus spp., e Pterophylla spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Anabrus simplex, Gryllotalpa africana, Gryllotalpa australis, Gryllotalpa brachyptera, Gryllotalpa hexadactila, Locusta migratoria, Microcentrum retinerve, Schistocerca gregaria, e Scudderia furcata.
[00199] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Sifonápteros. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Ceratophyllus gallinae, Ceratophyllus niger, Ctenocephalides canis, Ctenocephalides felis, e Pulex irritans.
[00200] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Tisanóopteros. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Caliothrips spp., Frankliniella spp., Scirtothrips spp., e Thrips spp. Uma lista não exaustiva de sp. Particular inclui, porém não está limitada a, Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella williamsi, Heliothrips haemorrhoidalis, Rhipiphorothrips cruentatus, Scirtothrips citri, Scirtothrips dorsalis, e Taeniothrips rhopalantennalis, Thrips hawaiiensis, Thrips nigropilosus, Thrips orientalis, Thrips tabaci.
[00201] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem de Thysanura. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Lepisma spp. e Thermobia spp.
[00202] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes da Ordem Acarina. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Acarus spp., Aculops spp., Boophilus spp., Demodex spp., Dermacentor spp., Epitrimerus spp., Eriophyes spp., Ixodes spp., Oligonychus spp., Panonychus spp., Rhizoglyphus spp., e Tetranychus spp. Uma lista não exaustiva de espécies particulares inclui, porém não está limitada a, Acarapis woodi, Acarus siro, Aceria mangiferae, Aculops lycopersici, Aculus pelekassi, Aculusschlechtendali, Amblyomma americanum, Brevipalpus obovatus, Brevipalpus phoenicis, Dermacentor variabilis, Dermatophagoides pteronyssinus, Eotetranychus carpini, Notoedres cati, Oligonychus coffeae, Oligonychus ilicis, Panonychus citri, Panonychus ulmi, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Rhipicephalus sanguineus, Sarcoptes scabiei, Tegolophus perseaflorae, Tetranychus urticae, e Varroa destructor.
[00203] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar peste da Ordem de Symphyla. Uma lista não exaustiva de sp. particular inclui, porém não está limitada a, Scutigerella immaculata.
[00204] Em outra modalidade, as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controlar pestes do Filo Nematoda. Uma lista não exaustiva de gêneros particulares, inclui, porém não está limitada a, Aphelenchoides spp., Belonolaimus spp., Criconemella spp., Ditylenchus spp., Heterodera spp., Hirschmanniella spp., Hoplolaimus spp., Meloidogyne spp., Pratylenchus spp., e Radopholus spp. Uma lista não exaustiva de sp. particular inclui, porém não está limitada a, Dirofilaria immitis, Heterodera zeae, Meloidogyne incognita, Meloidogyne javanica, Onchocerca volvulus, Radopholus similis, e Rotylenchulus reniformis.
[00205] Para informação adicional, consultar "HANDBOOK OF PEST CONTROL - THE BEHAVIOR, LIFE HISTORY, E CONTROL OF HOUSEHOLD PESTS" por Arnold Mallis, 9a Edição, copyright 2004 por GIE Media Inc.
[00206] Controle de pestes de Filos Nematoda, Artropoda, e/ou Molusca geralmente significa que as populações de peste, atividade de peste, ou ambas, são reduzidas em um local. Isto pode acontecer quando
[00207] (a) populações de peste são repelidas de um locus;
[00208] (b) pestes são incapacitadas em, ao redor, um locus; ou
[00209] (c) pestes são exterminadas em, ou ao redor, um locus.
[00210] Certamente, uma combinação destes resultados pode ocorrer. Geralmente, populações, atividades de peste ou ambas são desejavelmente reduzidas mais do que cinquenta por cento, preferivalmente mais do que 90 por cento, e mais preferivalmente mais do que 98 por cento. Geralmente, o locus não está em, ou sobre, um humano; consequentemente, o locus é geralmente um locus não humano.
[00211] Em outra modalidade, o locus ao qual uma molécula de Fórmula Um e/ou Fórmula Dois é aplicada pode ser qualquer locus que é habitado, ou que torna-se habitado, ou que pode ser atravessado, por uma peste dos Filos Nematoda, Artropoda, e/ou Molusca. Por exemplo, o locus pode ser:
[00212] (a) onde colheitas, árvores, frutas, cereais, forragens, vinhas, turfa e/ou plantas ornamentais, são cultivadas;
[00213] (b) onde animais domesticados residem;
[00214] (c) as superfícies interiors ou exteriores de construções (tal como lugares onde os grãos são armazenados);
[00215] (d) os materiais de construção usados em edifícios (tal como madeiras impregnadas); e
[00216] (e) o solo em torno das construções.
[00217] Áreas de colheita particulares para usar uma molécula Fórmula Um e/ou Fórmula Dois incluem áreas onde maçãs, milho, girassóis, algodão, soja, canola, trigo, arroz, sorgo, cevada, aveia, batatas, laranjas, alfafa, alface, morangos, tomates, pimentas, crucíferos, pêras, tabaco, amêndoas, beterraba açucareira, feijões e outras colheitas valiosas são cultivadas ou as sementes das mesmas que vão ser plantadas. É também vantajoso usar sulfato de amônio com uma molécula de Fórmula Um e/ou Fórmula Dois quando cultivando várias plantas.
[00218] Em outra modalidade, moléculas de Fórmula Um e/ou Fórmula Dois são geralmente usadas em quantidades de cerca de 0,0001 grama por hectare a cerca de 5000 gramas por hectare para fornecer controle. Em outra modalidade, é preferível que as moléculas de Fórmula Um e/ou Fórmula Dois sejam usadas em quantidades de cerca de 0,001 grama por hectare a cerca de 500 gramas por hectare. Em outra modalidade, é mais preferível que as moléculas de Fórmula Um e/ou Fórmula Dois sejam usadas em quantidades de cerca de 0,01 grama por hectare a cerca de 50 gramas por hectare.
[00219] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas em misturas, aplicadas simultânea ou sequencialmente, sozinhas ou com outros compostos para realçar o vigor da planta (por exemplo, para cultivar um melhor sistema de raiz, para melhor suportar as consições de cultivo estressantes). Outros tais compostos são, por exemplo, os compostos que modulam os receptores de etileno de planta, mais notavelmente, 1-metilciclopropeno (também conhecido como 1-MCP). Além disso, tais moléculas podem ser usadas durante momentos quando a atividade de peste é baixa, tal como antes das plantas que estão sendo cultivadas começarem a produzir produtos agrícolas valiosos. Tais momentos incluem a estação de plantio preoce quando a pressão de peste está geralmente baixa.
[00220] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser aplicadas às porções foliares ou frutíferas de plantas para controle de pestes. As moléculas entrarão em contato com a peste, ou a peste consumirá o pesticida quando comer a folha, massa da frura, ou seiva de extração, que contém o pesticida. As moléculas de Fórmula Um e/ou Fórmula Dois podem também ser aplicados ao solo, e quando aplicadas desta maneira, pestes que se alimentam da raiz e caule podem ser controladas. As raízes podem absorver uma molécula levando-a até às porções foliares da planta para controlar as pestes que se alimentam de seiva e mastigam solo.
[00221] Geralmente, com iscas, as iscas são colocadas no solo onde, por exemplo, os cupins podem entrar em contato com, e/ou ser atraídos para a isca. As iscas podem ser aplicadas a um superfície de uma construção, (superfície horizontal, vertical, ou inclinada) onde, por exemplo, formigas, cupins, baratas e moscas, podem entrar em contato com, e/ou ser atraídos para a isca. Iscas podem compreender uma molécula de Fórmula Um e/ou Fórmula Dois.
[00222] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser encapsuladas dentro, ou colocadas na superfície de uma cápsula. O tamanho das cápsulas pode variar do tamanho de nanômetro (de cerca de 100-900 nanômetros em diâmetro) para tamanho de micrômetro (de cerca de 10-900 mícrons em diâmetro).
[00223] Devido à capacidade exclusiva dos ovos de algumas pestes de resistirem a certos pesticidas, repetidas publicações das moléculas de Fórmula Um e/ou Fórmula Dois podem ser desejáveis para controlar larvas recentemente emergidas.
[00224] O movimento sistêmico de pesticidas em plantas pode ser utilizado para controlar pestes em uma porção da planta aplicando (por exemplo, pulverizando uma área) as moléculas de Fórmula Um e/ou Fórmula Dois a uma porção diferente da planta. Por exemplo, o controle de insetos que se alimentam de planta pode ser obtido por irrigação por gotejamento ou aplicação de sulco, tratando o solo com, por exemplo, encharque do solo pré- ou pós plantio, ou tratando as sementes de uma planta antes do plantio.
[00225] O tratamento de semente pode ser aplicado a todos os tipos de sementes, incluindo aqueles das quais plantas geneticamente modificadas para espressar traços especializados germinarão.
[00226] Exemplos representativos incluem aqueles expressando proteínas tóxicas à pestes invertebradas, tais como Bacillus thuringiensis ou outras toxinas inseticidas, aquelas expressando resistência a herbicida, tal como semente de "Roundup Ready", ou aqueles com genes estranhos "empilhados" que expressam toxicinas inseticidas, resistência a herbicida, realce de nutrição, resistência à seca, ou quaisquer outras características benéficas. Além disso, tais tratamentos de semente com as moléculas de Fórmula Um e/ou Fórmula Dois podem também realçar a capacidade d euma planta resistir melhor a condições de crescimento estressabtes. Isto resulta emu ma planta mais saudável e vigorosa, que pode levar a maiores rendimentos no momento da colheita. Geralmente, cerca de 1 grama das moléculas de Fórmula Um e/ou Fórmula Dois a cerca de 500 gramas por 100.000 sementes são esperados para fornecer bons benefícios, quantidades de cerca de 10 gramas a cerca de 100 gramas por 100.000 sementes são esperados para fornecer benefícios melhores, e quantidades de cerca de 25 gramas a cerca de 75 gramas por 100.000 sementes são esperados para fornecer benefícios ainda melhores.
[00227] Deve-se porntamente evidenciar que as moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas sobre, em, ou em torno de plantas geneticamente modificadas para expresser características especializadas, tal como Bacillus thuringiensis ou outras toxicinas inseticidas, ou aqueles que expressam resistência a herbicida, ou aqueles com genes estranhos "empilhados" que expressam toxicinas inseticidas, resistência a herbicida, realce de nutrição, ou quaisquer outras características benéficas.
[00228] As moléculas de Fórmula Um e/ou Fórmula Dois podem ser usadas para controle de endoparasitas e ectoparasitas no setor de medicina veterinária ou no campo da criação de animais não humanos. As moléculas de Fórmula Um e/ou Fórmula Dois são aplicadas, tal como por adminnistração oral na forma de, por exemplo, comprimidos, cápsulas, bebidas, grânulos, por aplicação dérmica na forma de, por exemplo, mergulho, vaporização, derramamento, manchamento, e polvilhamento, e por administração parenteral na forma de, por exemplo, uma injeção.
[00229] As moléculas de Fórmula Um e/ou Fórmula Dois podem também ser empregados vantajosamente na manutenção de criação, por exemplo, gado, ovelha, porcos, galinhas, e gansos. Elas podem também ser empregadas vantajosamente em animais de estimação tais como cavalos, cachorros, e gatos. As pestes para controlar seriam pulgas e carrapatos que são incômodo a tais animais. As formulações são administradas oralmente aos animais com água potável ou alimentação. As dosagens e formulações que são adequadas dependem das espécies.
[00230] As moléculas de Fórmula Um e/ou Fórmula Dois podem também ser usados para controle de vermes parasitário, especialmente do intestino, nos animais listados acima.
[00231] As moléculas de Fórmula Um e/ou Fórmula Dois podem também ser empregadas em métodos terapêuticos para assistência à saúde humana. Tais métodos incluem, porém não são limitados a, administração oral na forma de, por exemplo, comprimidos, cápsulas, bebidas, grânulos, e por aplicação dérmica.
[00232] As pestes em torno do mundo foram foram migrando para novos ambientes (para tal peste) e, após isso, tornando uma nova espécie invasiva em tal novo ambiente. As moléculas de Fórmula Um e/ou Fórmula Dois podem também ser usadas em tais novas espécies invasivas para controlá-las em tal novo ambiente.
[00233] As moléculas de Fórmula Um e/ou Fórmula Dois podem também ser usadas em uma área onde plantas, tais como colheitas, são desenvolvidas (por exemplo, pré-plantação, plantação, pré-colheita) e onde há baixos níveis (ainda nenhuma presença real) de pestes que podem comercialmente danificar tais plantas. O uso de tais moléculas em tal área é para beneficiar as plantas sendo desenvolvidas na área. Tais benefícios podem incluir, porém não estão limitados a, melhora da saúde de uma planta, melhora da produção de uma planta (por exemplo, biomassa aumentada e/ou teor aumentado de ingredientes valiosos), melhora do vigor de uma planta (por exemplo, melhor desenvolvimento da planta e/ou folhas mais verdes), melhora da qualidade de uma planta (por exemplo, teor ou composição melhorada de certos ingredientes), e melhora da tolerância a estresse abiótico e/ou biótico da planta.
[00234] Antes de um pesticida poder ser usado ou vendido comercialmente, tal pesticida sofre longos processos de avaliação por várias autoridades governamentais (locais, regiionais, estaduais, nacionais e internacionais). Os requisitos de dados volumosos são especificados por autoridades reguladoras e devem ser endereçados por meio de geração de dados e submissão pelo registrante do produto ou por um terceiro em nome do registrante do produto, frequentemente usando um computador com uma conecção à Rede Mundial de Computadores. Estas autoridades governamentais em seguida reveem tais dados e, se uma determinação de segurança é condluída, fornecem o usuário ou vendedor em potencial com aprovação de registro do produto. Após isso, naquela localidade onde o registro do produto é concedido e apoiado, tal usuário ou vendedor pode usar ou vender tal pesticida.
[00235] Uma molécula de acordo com a Fórmula Um e/ou Fórmula Dois pode ser testada para determinar sua eficácia contra pestes. Além disso, o modo dos estudos de ação pode ser conduzido para determinar se a referiuda molécula tem um modo diferente de ação daquela outras pesticidas. Após isso, tais dados requeridos podem ser disseminados, tais como pela internet, para terceiros.
[00236] Os títulos neste documento são por conveniência apenas e não devem ser usados para interpretar qualquer porção dos mesmos.
[00237] Em outra modalidade desta Invenção, as moléculas de Fórmula Um/Fórmula Dois podem ser usados em combinação (tal como, em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com um ou mais ingredientes ativos.
[00238] Em outra modalidade desta invenção, as moléculas de Fórmula Um/Fórmula Dois podem ser usadas em combinação (tal como, em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com um ou mais ingredientes ativos, cada um tendo uma MoA que é igual à, similar à, porém mais provavelmente - diferente de, MoA das moléculas de Fórmula Um/Fórmula Dois.
[00239] Em outra modalidade, moléculas de Fórmula Um/Fórmula Dois pode ser usado em combinação (tal como, em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com uma ou mais moléculas tendo propriedades acaricidas, algicidas, avicidas, bactericidas, fungicidas, herbicidas, inseticidas, moluscicidas, nematicidas, rodenticidas, e/ou virucidais.
[00240] Em outra modalidade, as moléculas de Fórmula Um/Fórmula Dois podem ser usadas em combinação (tal como, em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com uma ou mais moléculas que são antialimentícias, repelentes de aves, quimioesterilantes, protetores de herbicida, atrativos de inseto, repelentes de inseto, repelentes de mamíferos, disruptores de acasalamento, ativadores de planta, reguladores de crescimento de planta, e/ou sinérgicos.
[00241] Em outra modalidade, as moléculas de Fórmula Um/Fórmula Dois podem também ser usadas em combinação (tal como em uma mistura composicional, ou uma aplicação simultânea ou sequencial) com um ou mais biopesticidas.
[00242] Em outra modalidade, em uma composição pesticida, as combinações de uma molécula de Fórmula Um/Fórmula Dois e um ingrediente ativo podem ser usados em uma ampla variedade de relações de peso. Por exemplo, em uma mistura de dois componentes, a relação de peso de uma molécula de Fórmula Um/Fórmula Dois para um ingrediente ativo, as relações de peso na Tabela A podem ser usadas. Entretanto, em geral, as relações de peso menores do que cerca de 10:1 a cerca de 1:10 são preferidas. Pse refere, às vezes, usar mistura de três, quatro, cinco, seis, sete, ou mais componentes compreendendo uma molécula de Fórmula Um/Fórmula Dois e mais dois ou mais ingredientes ativos.
[00243] As relações de peso de uma molécula de Fórmula Um/Fórmula Dois para um ingrediente ativo podem também ser representadas como X:Y; em que X é as partes por peso de uma molécula de Fórmula Um/Fórmula Dois e Y é as partes por peso de ingrediente ativo. A faixa numérica das partes por peso para X é 0 < X <100 e as partes por peso para Y é 0 < Y < 100 e é mostrada graficamente na Tabela B. Por meio de exemplo não limitante, a relação de peso de uma molécula de Fórmula Um/Fórmula Dois para um ingrediente ativo pode ser 20:1.
[00244] As faixas de relações de peso de uma molécula de Fórmula Um/Fórmula Dois para um ingrediente ativo podem ser representadas como X1:Y1 para X2:Y2, em que X e Y são definidos como acima.
[00245] Em uma modalidade, a faixa de relações de peso pode ser X1:Y1 para X2:Y2, em que X1 > Y1 e X2 < Y2. Por meio de exemplo não limitante, a faixa de uma relação de peso de uma molécula de Fórmula Um/Fórmula Dois para um ingrediente ativo pode ser entre 3:1 e 1:3, incluindo as extremidades.
[00246] Em outra modalidade, a faixa de relações de peso pode ser X1:Y1 para X2:Y2, em que X1 > Y1 e X2 > Y2. Por meio de exemplo não limitante, a faixa de relação de peso de uma molécula de Fórmula Um/Fórmula Dois para um ingrediente ativo pode ser entre 15:1 e 3:1, incluindo as extremidades.
[00247] Em outra modalidade, a faixa de relações de peso pode ser X1:Y1 para X2:Y2, em que X1 < Y1 e X2 < Y2. Por meio de exemplo não limitante, a faixa de relações de peso de uma molécula de Fórmula Um/Fórmula Dois para um ingrediente ativo pode ser entre cerca de 1:3 e de cerca de 1:20, incluindo as extremidades.TABELA A
[00248] Prevê-se que certas relações de peso de uma molécula de Fórmula Um/Fórmula Dois para um ingrediente ativo, como representado na Tabela A e B, podem ser sinérgicas.TABELA B
[00249] Os compostos da presente invenção podem também ser úteis para aumentar o vigor de uma planta de colheita. Este método compreende por em contato a planta de colheita (por exemplo, folhagem, flores, frutas ou raízes) ou a semente da qual a planta de colheita é desenvolvida com um composto de Fórmula Um/Fórmula Dois em quantidade suficiente para obter o efeito desejado do vigor da planta (isto é, quantidade biologicamente eficaz). Tipicamente, o composto de Fórmula Um/Fórmula Dois é aplicado em uma composição formulada. Embora o composto de Fórmula Um/Fórmula Dois seja frequentemente direcionado à planta de colheita ou sua semente, ele pode também ser aplicado no local da planta de colheita, isto é, o ambiente da planta de colheita, particularmente a porção do ambiente em proximidade suficiente para permitir que o composto de Fórmula Um/Fórmula Dois migre para a planta de colheita. O local relevante a este método mais comumente compreende o meio de crescimento (isto é, meio que fornece nutrientes para a planta), tipicamente, o solo em que a planta é desenvolvida. O tratamento de uma planta de colheita para aumentar o vigor da planta de colheita, desse modo, compreende por em contato a planta de colheita, a semente da qual a planta de colheita é desenvolvida ou o local da planta de colheita com a quantidade biologicamente eficaz de um composto de Fórmula Um/Fórmula Dois.
[00250] O vigor aumentado da colheita pode resultar em um ou mais dos seguintes efeitos observados: (a) estabelecimento ideal de colheita como demonstrado pela excelente germinação de semente, emergência de colheita e suporte de colheita; (b) desenvolvimento realçado de colheita como demonstrado pelo rápido e robusto desenvolvimento de folhas (por exemplo, medido por índice de área foliar), altura de planta, número de perfilhos (por exemplo, para arroz), massa radicular e peso seco total de massa vegetativa da colheita; (c) rendimentos melhorados de colheita, como demonstrado por tempo de florescimento, duração de florescimento, número de flores, acúmulo total biomassa (isto é, quantidade de produção) e/ou graua de comerciabilidade de produção de frutas ou grão (isto é, qualidade de produção); (d) capacidade realçada da colheita resistir a ou impedir infecções de doença de planta e infestações por pestes de artrópode, nematoides ou molucos; e (e) capacidade aumentada da colheita de resistir a estresses ambientais tal como exposição a extremos térmicos, umidade subideal ou produtos químicos fitotóxicos.
[00251] Os compostos da presente invenção podem aumentar o vigor de plantas tratadas em comparação com plantas não tratadas matando ou, de outro modo, impedindo a alimentação de pestes de invertebrados fitófagos no ambiente das plantas. Na ausância de tal controle de pestes de invertebrados fitófagos, as pestes reduzem o vigor da planta consumindo o tecido vegetal ou seiva, ou transmitindo patógenos de planta tais como vírus. Mesmo na ausência de pestes de invertebrados fitófagos, os compostos da presente invenção podem aumentar o vigor das plantas modificando o metabolismo delas. Geralmente, o vigor de uma planta de colheita será mais significativamente aumentado tratando-se a planta com um composto da invenção, se a planta for desenvolvida em um ambiente não ideal, isto é, um ambiente compreendendo um ou mais aspectos adversos á planta, obtendo o potencial genético total que ela exibiria em um ambiente ideal.
[00252] É de se observar o presente método para aumento do vigor de uma planta de colheita em que a planta de colheita é desenvolvida em um ambiente que compreende pestes de invertebrados fitófagos. Além disso, é de se observar o presente método para aumento do vigor de uma planta de colheita em que a planta de colheita é desenvolvida em um ambiente que não compreende pestes de invertebrados fitófagos. Além disso, é de se observar o presente método para aumento do vigor de uma planta de colheita em que a planta de colheita é desenvolvida em um ambiente que compreende uma quantidade de mistura menor do que o ideal para suportar o desenvolvimento de uma planta de colheita. É de se observar o presente método para aumento do vigor de uma planta de colheita em que a colheita é de arroz. Além disso, é de se observar o presente método para aumento do vigor de uma planta de colheita em que a colheita é de milho. Além disso, é de se observar o presente método para aumento do vigor de uma planta de colheita em que a colheita é de seja.
[00253] Os compostos desta invenção podem também ser misturados com um ou mais outros compostos ou agentes biologicamente ativos que incluem inseticidas, fungicidas, nematocidas, bactericidas, acaricidas, herbicidas, protetores de herbicida, reguladores de crescimento tal como inibidores de muda de insetos e estimuladores de enraizamento, quimioesterilantes, produtos semioquímicos, repelentes, atraentes, fenômenos, estimulantes de alimentação, outros compostos biologicamente ativos ou bactérias entomopatogênicas, vírus ou fungos para formar um pesticida de múltiplos componentes dando um espectro ainda mais amplo de utilidade agronômica e não agronômica. Desse modo, a presente invenção também pertence a uma composição que compreende a quantidade biologicamente eficaz de um composto de Fórmula Um/Fórmula Dois, pelo menos um componente adicional selecionado do grupo que consiste em tensoativos, diluentes sólidos e diluentes líquidos, e pelo menos um composto ou agente biologicamente ativo adicional. Para as misturas da presente invenção, os outros compostos ou agentes biologicamente ativos podem ser formulados juntamente com os compostos presentes, incluindo os compostos de Fórmula Um/Fórmula Dois, para formar uma pré-mistura, ou os outros compostos ou agentes biologicamente ativos podem ser formulados separadamente dos compostos presentes, incluindo os compostos de Fórmula Um/Fórmula Dois, e as duas formulações combinadas juntamente antes da aplicação (por exemplo, em um tanque de vaporização) ou, alternativamente, aplicadas em sucessão.
[00254] Os exemplos de such compostos ou agentes biologicamente ativos com os quais os compostos desta invenção podem ser formulados são inseticidas tais como abamectina, acefato, acequinocila, acetamiprida, acrinatrina, acinonapir, afidopiropen ([(3S,4R,4ar,6S,6a S,12R,12aS,12bS)-3- [(ciclopropilcarbonil)oxi]-1,3,4,4a,5,6,6a,12,12a, 12b-deca-hidro-6,12-di-hidróxi-4,6a,12b- trimetil-11-oxo-9-(3-piridinil)- 2H,11H-nafto[2,1-b]pirano[3,4-e]piran-4-il]metil ciclopropanocarboxilato), amidoflumete, amitraz, avermectina, azadiractina, azinfos-metila, benfuracarbe, bensultape, benzpirimoxano, bifentrina, bifenazato, bistriflurona, borato, buprofezina, cadusafós, carbarila, carbofurano, cartap, carzol, clorantraniliprol, clorfenapir, clorfluazurona, clorpirifós, clorpirifós-metila, cromafenozida, clofentezina, clotianidina, ciantraniliprol (3-bromo-1-(3- cloro-2-piridinil)-N-[4-ciano-2-metil-6-[(metilamino)carbo nil]fenil]-1H- pirazol-5-carboxamida), ciclaniliprol (3-bromo-N-[2-bromo-4-cloro-6- [[(1- ciclopropiletil)amino]carbonil]fenil]-1-(3-cloro-2-piridinil)-1H-pirazol- 5-carboxamida), cicloprotrina, cicloxaprida ((5S,8R)-1-[(6-cloro-3- piridinil)metil]- 2,3,5,6,7,8-hexa-hidro-9-nitro-5,8-epóxi-1H-imidazo[1,2- a]azepina), ciflumetofeno, ciflutrina, beta-ciflutrina, cihalotrina, gamma- cihalotrina, lambda-cihalotrina, cipermetrina, alfa-cipermetrina, zeta- cipermetrina, ciromazina, deltametrina, diafentiuron, diazinon, dieldrina, diflubenzurona, dimeflutrina, dimehipo, dimetoato, dinotefurano, diofenolano, emamectina, endosulfan, esfenvalerato, etiprol, etofenpróx, etoxazol, fenbutatin oxida, fenitrotiona, fenotiocarbe, fenoxicarbe, fenpropatrina, fenvalerato, fipronil, flometoquina (carbonato de 2-etil-3,7-dimetil-6-[4-(trifluorometóxi)fenóxi]-4-quinolinil metila), flonicamida, fluazaindolizina, flubendiamida, flucitrinato, flufenerim, flufenoxuron, flufenoxistrobina ((αE)-2-[[2-cloro-4- (trifluorometil)fenoxi] metil]-α- (metoximetileno)benzenoacetato de metila), fluensulfona (5-cloro-2-[(3,4,4-trifluoro-3-buten-1- il)sulfonil]tiazol), fluhexafon, flufiprol (1-[2,6-dicloro-4- (trifluorometil)fenil]-5-[(2-metil-2-propen-1-il)amino]-4- [(trifluorometil)sulfinil]-1H-pirazol-3-carbonitrila), flupiradifurona (4-[[(6- cloro-3-piridinil)metil](2,2- difluoroetil)amino]-2(5H)-furanona), flipirimina, fluvalinato, tau-fluvalinato, fonofós, formetanato, fostiazato, halofenozida, heptaflutrina (2,2-dimetil-3-[(1Z)-3,3,3-trifluoro-1-propen- 1-il]ciclopropanocarboxilato de [2,3,5,6-tetrafluoro-4-(metoximetil)fenil] metila), hexaflumurona, hexitiazóx, hidrametilnona, imidacloprida, indoxacarbe, sabões inseticidas, isofenfós, lufenurona, malationa, meperfutrina ((1R,3S)-3-(2,2-dicloroetenil)-2,2- dimetilciclopropanocarboxilato de [2,3,5,6-tetrafluoro-4- (metoximetil)fenil]metila), metaflumizona, metaldeida, metamidofos, metidationa, metiocarbe, metomila, metopreno, metoxiclor, metoxifenozida, metoflutrina, monocrotofós, monofluorotrina (3-(2- ciano-1-propen-1-il)-2,2- dimetilciclopropanocarboxilato de [2,3,5,6- tetrafluoro-4- (metoximetil)fenil]metila), nicotina, nitenpiram, nitiazina, novalurona, noviflumurona, oxamila, oxazosulfila, parationa, paration- metila, permetrina, forato, fosalona, fosmete, fosfamidona, pirimicarbe, profenofós, proflutrina, propargita, protrifenbuto, piflubumida (1,3,5- trimetil-N-(2-metil-1-oxopropil)-N-[3-(2-metilpropil)-4-[2,2,2-trifluoro-1- metóxi-1-(trifluorometil)etil]fenil]-1H-pirazol-4-carboxamida), pimetrozina, pirafluprol, piretrina, piridabeno, piridalila, pirifluquinazona, piriminostrobina ((αE)-2-[[[2-[(2,4-diclorofenil)amino]-6-(trifluorometil)-4- pirimidinil]oxi]metil]-α-(metoximetileno)benzenoaceta to de metila), piriprol, piriproxifeno, rotenona, rianodina, esilafluofeno, espinetoram, espinosada, espirodiclofeno, espirodiona, espiromesifeno, espirotetramato, esulprofós, esulfoxaflor (N-[metiloxido[1-[6- (trifluorometil)-3-piridinil]etil]-À4- esulfanilideno]cianamida), tebufenozida, tebufenpirada, teflubenzurona, teflutrina, terbufós, tetraclorvinfós, tetrametrina, tetrametilfutrina ([2,2,3,3- tetrametilciclopropanocar boxilato de 2,3,5,6-tetrafluoro-4- (metoximetil)fenil]metila), tetraniliprol, tiacloprida, tiametoxam, tiodicarbe, tiosultap-sódio, tioxazafen (3-fenil-5-(2-tienil)-1,2,4- oxadiazol), tolfenpirada, tralometrina, triazamato, triclorfon, triflumezopirim (sais internos de 2,4-dioxo-1-(5-pirimidinilmetil)-3-[3- (trifluorometil)fenil]-2H-pirido[1,2-a]pirimidínio), triflumurona, ticlopirazoflor, Delta-endotoxinas de Bacillus turingiensis, bactérias entomopatogenéticas, vírus entomopatogênicos e fungos entomopatogênicos.
[00255] São de se observar inseticidas tais como abamectina, acetamiprida, acrinatrina, acinonapir, afidopiropen, amitraz, avermectina, azadiractina, benfuracarbe, bensultape, benzpirimoxano, bifentrina, buprofezina, cadusafós, carbarila, cartap, clorantraniliprol, clorfenapir, clorpirifós, clotianidina, ciantraniliprol, ciclaniliprol, cicloprotrina, ciflutrina, beta-ciflutrina, cihalotrina, gamma-cihalotrina, lambda-cihalotrina, cipermetrina, alfa-cipermetrina, zeta-cipermetrina, ciromazina, deltametrina, dieldrina, dinotefurano, diofenolano, emamectina, endosulfan, esfenvalerato, etiprol, etofenpróx, etoxazol, fenitrotiona, fenotiocarbe, fenoxicarbe, fenvalerato, fipronil, flometoquina, flonicamida, flubendiamida, flufenoxuron, flufenoxistrobina, flufensulfona, flupiprol, flupiradifurona, flupirimina, fluvalinato, formetanato, fostiazato, heptaflutrina, hexaflumurona, hidrametilnona, imidacloprida, indoxacarbe, lufenurona, meperflutrina, metaflumizona, metiocarbe, metomila, metopreno, metoxifenozida, metoflutrina, monofluorotrina, nitenpiram, nitiazina, novalurona, oxamila, oxazosulfila, piflubumida, pimetrozina, piretrina, piridabeno, piridalila, piriminostrobina, piriproxifeno, rianodina, espinetoram, espinosada, espirodiclofeno, espiromesifeno, espiropidion, espirotetramato, esulfoxaflor, tebufenozida, tetrametrina, tetrametilflutrina, tiacloprida, tiametoxam, tiodicarbe, tiosultap-sódio, tralometrina, triazamato, triflumezopirim, triflumurona, ticlopirazoflor, Delta-endotoxinas de Bacillus turingiensis, todas as linhagens de Bacillus turingiensis e todas as linhagens de vírus de poliedrose nuclear.
[00256] Uma modalidade dos agentes biológicos para mistura com compostos desta invenção inclui bactérias entomopatogênicas tal como Bacillus thuringiensis, e as delta-endotoxinas encapsuladas de Bacillus thuringiensis tais como bioinseticidas de MVP® e MVPII® preparados pelo processo de CellCap® (CellCap®, MVP® e MVPII® são marcas registradas de Mycogen Corporation, Indianápolis, Indiana, Estados Unidos da América); fungos entomopatogênicos tal como fungo muscardina verde; e vírus entomopatogênico (tanto de ocorrência natural quanto geneticamente modificado) incluindo baculovírus, nucleopolihedrovírus (NPV) tal como Helicoverpa zea nucleopolihedrovírus (HzNPV), nucleopolihedrovírus de Anagrapha falcifera (AfNPV); e vírus de granulose (GV) tal como vírus de granulose de Cydia pomonella (CpGV).
[00257] De observação particular é uma tal combinação em que o ingrediente ativo de controle de peste invertebrada pertence a uma diferente classe química ou tem um diferente sítio de ação do que o composto de Fórmula Um/Fórmula Dois. Em certos casos, uma combinação com pelo menos um ingrediente ativo de controle de peste invertebrada tendo um espectro similar de controle, porém um sítio diferente de ação, será particularmente vantajosa para controle de resistência. Desse modo, uma composição da presente invenção pode compreender uma quantidade biologicamente eficaz de pelo menos um ingrediente ativo de controle de peste invertebrada adicional tendo um espectro similar de controle, porém pertecendo a uma classe química diferente ou tendo um diferente sítio de ação. Estes compostos biologicamente ativos e agentes adicionais incluem, porém não estão limitados a, inibidores de acetilcolinesterase (AChE) tais como os metomila de carbamatos, oxamila, tiodicarbe, triazamato, e os organofosfatos de clorpirifós; antagonistas de canal de cloreto controlados por GABA tais como os ciclodienos dieldrina e endossulfan, e os fenilpirazóis etiprol e fipronila; moduladores de canal de sódio tais como os piretroides bifentrina, ciflutrina, beta- ciflutrina, cihalotrina, lambda-cihalotrina, cipermetrina, deltametrina, dimeflutrina, esfenvalerate, metoflutrina e proflutrina; agonistas de receptores de acetilcolina nicotínicos (nACR) tais como os neonicotinoides acetamiprida, clotianidina, cicloxaprida, dinotefurano, flupirimina, imidacloprida, imidaclotiz; nitenpiram, nitiazina, paicongding, tiacloprida, e tiametoxam; a sulfoximina, sulfoxaflor; a butenolida, flupiradifurona; e mesoiônicos tais como dicloromezotiaz e triflumezopirim; ativadores de receptor de acetilcolina nicotínicos (nACR) tais como as espinosinas espinetoram e espinosad; ativadores de canal de cloreto tais como as avermectinas abamectina, emamectina, milbemectina, lepimectina, moxidectina, mibemicina oxima; miméticos de hormônio juvenis tais como diofenolano, metopreno, fenoxicarbe e piriproxifeno; moduladores de canal de TRPV de órgão cordotonal tais como pimetrozina, pirifluquinazona e inibidores de crescimento de afidopiropenmite tais como clofentezina, diflovidazina, hexitiazox e etoxazol; inibidores de ATP sintase mitocondrial tal como propargita; desacopladores de fosforilação oxidativa por meio de ruptura do gradiente de próton tal como clorfenapir; bloqueadores de canal de receptor de acetilcolina nicotínicos (nACR) tais como os análogos de nereistoxina cartap; inibidores de biossíntese de quitina tais como as benzoilureias flufenoxurona, hexaflumurona, lufenurona, novalurona, noviflumurona e triflumurona, e buprofezina; disruptores de muda dipteran tal como ciromazina; agonistas de receptor de ecdisona tais como as diacil- hidrazinas metoxifenozida e tebufenozida; agonistas de receptor de octopamina tal como amitraz; inibidores de transporte de elétron de complexo III mitocondrial tal como hidrametilnona; inibidores de transporte de elétron de complexo I mitocondrial tal como piridabeno; bloqueadores de canal de sódio dependente de voltagem tais como indoxacarbe e metaflumizona; inibidores de acetil CoA carboxilase tais como os ácidos tetrônicos e tetrâmicos espirodiclofeno, espiromesifeno, espiropidiona, AC-118, e espirotetramate; inibidores de transporte de elétron de complexo II mitocondrial tais como as β-cetonitrilas cienopirafeno e ciflumetofeno; moduladores de receptor de rianidina tais como as diaminas antranílicas clorantraniliprol, ciantraniliprol, tetraniliprol, cihalodiamida, e ciclaniliprol, diamidas tais como flubendiamida, e ligantes de receptor de rianodina tal como rianodina; moduladores de órgão cordotonal tais como flonicamida; compostos em que o sítio alvo responsável pela atividade biológica é desconhecido ou não caracterizado tal como acinonapir, azadiractina, benzpirimoxano, bifenazato, flometoquina, fluhexafona, oxazossulfila, piridalila, e disruptores microbianos ticlopirazoflor de membranas de intestino de inseto tal como Bacillus turingensis e as delta-endotoxinas produzem e Bacillus esphaericus; e agentes biológicos incluindo nucleo polihedro viruses (NPV) e outros vírus inseticidas geneticamente modificados ou de ocorrrência natural.
[00258] Outros exemplos de compostos ou agentes biologicamente ativos com os quais os compostos desta invenção podem ser formulados são: fungicidas tais como acibenzolar-S-metila, aldimorf, ametoctradina, aminopirifeno, amisulbrom, anilazina, azaconazol, azoxistrobina, benalaxil (incluindo benalaxil-M), benodanila, benomila, bentiavalicarbe (incluindo bentiavalicarbe-isopropila), benzovindiflupir, betoxazina, binapacrila, bifenila, bitertanol, bixafeno, blasticidina-S, boscalida, bromuconazol, bupirimato, butiobato, carboxina, carpropamida, captafol, captan, carbendazim, cloronabe, clorotalonil, clozolinato, hidróxido de cobre, oxicloreto de cobre, sulfato de cobre, coumoxistrobina, ciazofamida, ciflufenamida, cimoxanil, ciproconazol, ciprodinil, diclobentiazóx, diclofluanida, diclocimet, diclomezina, dicloran, dietofencarbe, difenoconazol, diflumetorim, dimetirimol, dimetomorf, dimoxistrobina, diniconazol (incluindo diniconazol-M), dinocape, dipimetitrona, ditianona, ditiolanos, dodemorf, dodina, econazol, etaconazol, edifenfós, enoxastrobina (também conhecida como enestroburina), epoxiconazol, etaboxam, etirimol, etridiazol, famoxadona, fenamidona, fenaminstrobina, fenarimol, fenbuconazol, fenfuram, fenhexamida, fenoxanila, fenpiclonila, fenpicoxamida, fenpropidina, fenpropimorf, fenpirazamina, acetato de fentina, hidróxido de fentina, ferbam, ferimzona, flometoquina, florilpicoxamida, fluazinam, fludioxonil, flufenoxistrobina, fluindapir, flumorf, fluopicolida, fluopimomida, fluopiram, fluoxastrobina, fluquinconazol, flusilazol, flusulfamida, flutianil, flutolanil, flutriafol, fluxapiroxad, folpet, ftalida (também conhecida como ftalida), fuberidazol, furalaxila, furametpir, hexaconazol, himexazol, guazatina, imazalil, imibenconazol, albesilato de iminoctadina, triacetato de iminoctadina, inpirfluxam, iodicarbe, ipconazol, ipfentrifluconazol, ipflufenoquina, isofetamida, isoflucipram, iprobenfós, iprodiona, iprovalicarbe, isoprotiolana, isopirazam, isotianil, casugamicina, cresoxim-metila, mancozeb, mandipropamida, mandestrobina, maneb, mapanipirina, mefentrifluconazol, mepronil, meptildinocape, metalaxil (incluindo metalaxil-M/mefenoxam), metconazol, metassulfocarbe, metiram, metominostrobina, metrafenona, metiltetraprol, miclobutanil, naftitina, neo-asozina (metanoarsonato férrico), nuarimol, octilinona, ofurace, orisastrobina, oxadixila, oxatiapiprolina, ácido oxolínico, oxpoconazol, oxicarboxina, oxitetraciclina, penconazol, pencicuron, penflufeno, pentiopirad, perfurazoato, ácido fosfórico (incluindo sais dos mesmos, por exemplo, fosetil-alumina), picarbutratox, picoxistrobina, piperalina, polioxina, probenazol, procloraz, procimidona, propamocarbe, propiconazol, propinebe, proquinazida, protiocarbe, protioconazol, pidiflumetofeno, piraclostrobina, pirametostrobina, piraoxistrobina, pirapropoína, piraziflumida, pirazofos, piribencarbe, piributacarbe, pirifenox, piriofenona, perisoxazol, piridaclometila, pirimetanil, pirifenox, pirrolnitrina, piroquilona, quinconazol, quinmetionato, quinofumelina, quinoxifeno, quintozeno, esiltiofam, sedaxano, simeconazol, espiroxamina, estreptomicina, enxofre, tebuconazol, tebufloquina, tecloftalam, tecloftalam, tecnazeno, terbinafina, tetraconazol, tiabendazol, tifluzamida, tiofanato, tiofanato-metila, tiram, tiadinil, tolclofos-metila, tolprocarbe, tolifluanida, triadimefon, triadimenol, triarimol, triazóxido, sulfato de cobre tribásico, triclopiricarbe, tridemorf, trifloxistrobina, triflumizol, trimoprhamida triciclazol, triforina, triticonazol, uniconazol, validamicina, valifenalato (também conhecido como valifenal), vinclozolina, zinebe, ziram e zoxamida; nematocidas tais como fluopiram, espirotetramato, tiodicarbe, fostiazato, abamectina, iprodiona, fluensulfona, dissulfeto de dimetila, tioxazafeno, 1,3- dicloropropeno (1,3-D), metam (sódio e potássio), dazomet, cloropicrina, fenamifos, etoprofós, cadusafós, terbufós, imiciafos, oxamila, carbofurano, tioxazafeno, Bacillus firmus e Pasteuria nishizawae; bactericidas tal como estreptomicina; acaricidas tais como amitraz, cinometionat, clorobenzilato, cihexatina, dicofol, dienoclor, etoxazol, fenazaquina, óxido de fenbutatina, fenpropatrina, fenpiroximato, hexitiazóx, propargita, piridabeno e tebufenpirada.
[00259] Em certos casos, as combinações de um composto desta invenção com outros compostos ou agentes biologicamente ativos (particularmente, controle peste de invertebrados), (isto é, ingrediente ativos), podem resultar em um um efeito maior do que de um aditivo (isto é, sinérgico). A redução da quantidade de ingredientes ativos liberada no ambiente, ao mesmo tempo em que assegurando o controle de peste eficaz é sempre desejável. Quando o sinergismo de ingredientes ativos de controle de peste de invertebrados ocorre em taxas de aplicação que dão níveis agronomicamente satisfatórios de controle de peste de invertebrados, tais combinações podem ser vantajosas para reduzir o custo de produção de colheita e diminuir a carga ambiental.
[00260] Os compostos desta invenção e composições dos mesmos podem ser aplicados a plantas geneticamente tranformadas para expressar proteínas tóxicas a pestes de invertebrados (tais como delta- endotoxinas de Bacillus thuringiensis). Tal aplicação pode fornecer um espectro mais amplo de proteção de planta e ser vantajosa para o gerenciamento da resistência. O efeito dos compostos de controle de peste de invertebrados exogenamente aplicados desta invenção pode ser sinérgico com as proteínas de toxinas expressas.
[00261] As referências gerais para estes protetores agrícolas (isto é, agentes inseticidas, fungicidas, nematocidas, acaricidas, herbicidas e biológicos) incluem The Pesticide Manual, 13a Edição, C. D. S. Tomlin, Edição, British Crop Protection Council, Farnham, Surrey, U.K., 2003 e The BioPesticide Manual, 2a Edição, L. G. Copping, Edição, British Crop Protection Council, Farnham, Surrey, U.K., 2001.
[00262] Os compostos desta invenção podem ser combinados ou formulados com polinucleitídeos incluindo, porém não limitados a, DNA, RNA, e/ou nucleotídeos quimicamente modificados que influenciam a quantidade de um alvo particular por meio de desregulação, interferência, supressão ou silenciamento da transcrição geneticamente derivada que rende um efeito inseticida.
[00263] Para as modalidades onde um ou mais destes vários parceiros de mistura são usados, a relação de pesodestes vários parceiros de mistura (no total) para o composto de Fórmula Um/Fórmula Dois é tipicamente entre cerca de 1:3000 e de cerca de 3000:1. São de se observar as relações de peso entre cerca de 1:300 e de cerca de 300:1 (por exemplo ratios entre cerca de 1:30 e de cerca de 30:1). Alguém versado na técnica pode facilmente determinar, através de experimentação simples, as quantidades biologicamente eficazes de ingrediente ativos necessárias para o espectro desejado de atividade biológica. Será evidente que a inclusão destes componentes adicionais pode expandir o espectro de pestes de invertebrados controladas além do espectro controlado pelo composto de Fórmula Um/Fórmula Dois apenas.
[00264] A Tabela C lista as combinações específicas de um composto de Fórmula Um/Fórmula Dois com outros agentes de controle de peste de invertebrados ilustrativos das misturas, composições e métodos da presente invenção. A primeira coluna da Tabela C lista os agentes de controle de peste de invertebrados específicos (por exemplo, "Abamectina" na primeira linha). A segunda coluna da Tabela C lista o modo de ação (se conhecido) ou classe química dos agentes de controle de peste de invertebrados. A terceira coluna da Tabela C lista a(s) modalidade(s) de faixas de relações de peso para as taxas em que o agente de controle de peste de invertebrados pode ser aplicado em relação a um composto de Fórmula Um/Fórmula Dois (por exemplo,"50:1 a 1:50" de abamectina em relação a um composto de Fórmula Um/Fórmula Dois por peso).
[00265] Desse modo, por exemplo, a primeira linha da Tabela C especificamente descreve a combinação de um composto de Fórmula Um/Fórmula Dois com abamectina pode ser aplicada em uma relação de peso entre 50:1 e 1:50. As linhas restantes da Tabela C devem ser interpretadas similarmente. Em observação adicional, a Tabela C lista as combinações específicas de um composto de Fórmula Um/Fórmula Dois com outros agentes de controle de peste de invertebrados ilustrativos das misturas, composições e métodos da presente invenção e inclui modalidades adicionais de faixas de relação de peso para taxas de aplicação.
SEÇÃO DE TABELA
[00266] Moléculas (compostos) de acordo com a Fórmula Um e/ou Fórmula Dois como descrito na Tabela 1 e Tabela 2, aqui são testadas para determinar sua eficácia contra pestes, e geralmente mostram atividades nas categorias A e/ou B.
Claims (1)
1. Molécula caracterizada pelo fato de que apresenta uma estrutura selecionada do grupo consistindo em:
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JP7042829B2 (ja) | 2022-03-28 |
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