JP7042829B2 - Molecules with certain pest control usefulness and related intermediates, compositions and methods - Google Patents

Description

Cross-reference to related applications This application is a US provisional application No. 62 / 437,323 filed on December 21, 2016 and No. 62 / 464,429 filed on February 28, 2017. Claiming the benefits of the specification and the priority from them, those applications are by citation, the entire description of which is the content of the invention.

Fields of Disclosure This disclosure describes molecules with pest control usefulness against pests of the phylum Linear, Pseudomorphic and Pseudomonas aeruginosa, methods for producing such molecules and intermediates used in such methods. With respect to methods of making such molecules, compositions containing such molecules and methods of using such molecules against such pests. These molecules may be used, for example, as nematodes, acaricides, insectides, acaricides and mollusc repellents.

Background of Disclosure "Most of the most dangerous human diseases are transmitted by insect vectors" (Non-Patent Document 1). Historically, disease-borne diseases such as malaria, dengue, yellow fever, pesto and syllami-mediated rash typhoid (vector-born disorders) have been more than all other combined causes throughout the 1600s and early 1900s. He was responsible for many human illnesses and deaths (Non-Patent Document 2). Currently, pathogen-borne diseases are responsible for approximately 17% of global parasitic and infectious diseases. It has been estimated that about 250 million people worldwide suffer from malaria each year and about 800,000 die-85% of these deaths are children under the age of five. An additional 250,000 to 500,000 cases of hemorrhagic dengue occur each year (Non-Patent Document 3). Pathogen control plays an important role in the prevention and control of infectious diseases. However, pesticide resistance, including resistance to multiple pesticides, has emerged in all insect species that are the major pathogens of human disease (Non-Patent Document 1).

Each year, insects, phytopathogens and weeds destroy more than 40% of all possible food production. This loss occurs regardless of the application of pest control agents and the use of a variety of non-chemical controls such as crop rotation and biological controls. If any of these foods can be saved, they can be used to feed more than 3 billion malnourished people worldwide (Non-Patent Document 4).

Plant-parasitic nematodes are among the most prevalent pests and are often one of the most insidious and expensive. It has been estimated that the losses that can be attributed to nematodes range from about 9% in developed countries to about 15% in developing countries. However, in the United States, a survey of 35 states on various crops showed up to 25% nematode-derived loss (Non-Patent Document 5).

Abalones (slugs and snails) are less economically important pests than insects or nematodes, but in some areas abalone significantly reduce yields and have a significant impact on the quality of harvested products. It is also noted that it can transmit diseases of humans, animals and plants. Only a few dozen species of abalone are serious regional pests, while some are important pests on a global scale. In particular, abdominal crops include cultivated crops, pastoral crops and fiber crops; vegetables; bush fruits and tree fruits; herbs; and a variety of agriculture and horticulture such as ornamental plants. Affects crops (Non-Patent Document 6).

Termites cause damage to all types of private and public structures as well as agricultural and forest resources. In 2003, termites were estimated to cause more than US $ 20 billion in damages worldwide each year (Non-Patent Document 7).

Therefore, new pest control agents are needed for many reasons, including those mentioned above.

Rivero, A. et al. , Insect Control of Vector-Bone Diseases: When is Insect Response a Problem? Public Library of Science Pathogens, 6 (8) (2010) Gubler D. , Resurgent Vector-Borne Diseases as a Global Health Problem, Emerging Infectious Diseases, Vol. 4, No. 3, July-September (1988) Matthews, G.M. , Integrated Vector Management: Controlling vector of malaria and other insect vector brain disorders (2011) Basical, D.I. , Pest Control in World Agriculture, Agricultural Sciences-Vol. II (2009) Nicol, J. et al. et al. , Current Nematodes Threats to World Agriculture, Molecular and Molecular Genetics of Plant-Nematode Interactions (Eds. Jones, J. et al.), 2, Pattern. Speaker, B.I. , Molluscides, Encyclopedia of Pest Management (2002) Su, N. Y. , Overview of the global distribution and control of the Formosan subterranean termite, Sociobiology 2003, 41, 177-192

Definitions The examples given in the definitions are generally non-exhaustive and should not be considered limiting the molecules disclosed in this document. It is understood that the substituent should comply with the chemical bond rules and steric compatibility constraints associated with the particular molecule to which it is attached.

"Alkenyl" means an acyclic unsaturated (at least one carbon-carbon double bond) branched or non-branched substituent consisting of carbon and hydrogen, such as vinyl, allyl, butenyl, pentenyl and hexenyl. do.

"Alkenyloxy" means an alkenyl that further comprises only a carbon-oxygen single bond, such as allyloxy, butenyloxy, pentenyloxy, hexenyloxy.

"Alkoxy" means an alkyl that further comprises only a carbon-oxygen single bond, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy and tert-butoxy.

"Alkyl" means acyclic saturated, branched or non-branched substituents consisting of carbon and hydrogen, such as methyl, ethyl, propyl, isopropyl, butyl and tert-butyl.

"Alkynyl" means an acyclic unsaturated (at least one carbon-carbon triple bond) consisting of carbon and hydrogen, branched or non-branched substituents such as ethynyl, propargyl, butynyl and pentynyl.

"Alkynyloxy" means an alkynyl that further comprises only a carbon-oxygen single bond, such as pentynyloxy, hexynyloxy, heptynyloxy and octynyloxy.

"Aryl" means a cyclic aromatic substituent consisting of hydrogen and carbon, such as phenyl, naphthyl and biphenyl.

"Cycloalkenyl" is a monocyclic or polycyclic, unsaturated (at least one carbon-carbon double bond) substituent consisting of carbon and hydrogen, such as cyclobutenyl, cyclopentenyl, cyclohexenyl, norbornenyl, bicyclo [2.2]. .2] Means octenyl, tetrahydronaphthyl, hexahydronaphthyl and octahydronaphthyl.

"Cycloalkenyloxy" means cycloalkenyl that further comprises only a carbon-oxygen single bond, such as cyclobutenyloxy, cyclopentenyloxy, norbornenyloxy and bicyclo [2.2.2] octenyloxy.

"Cycloalkyl" means a monocyclic or polycyclic, saturated substituent consisting of carbon and hydrogen, such as cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, bicyclo [2.2.2] octyl and decahydronaphthyl.

"Cycloalkoxy" means cycloalkyls further comprising only a carbon-oxygen single bond, such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, norbornyloxy and bicyclo [2.2.2] octyloxy.

"Halo" means fluoro, chloro, bromo and iodine.

"Haloalkoxy" is an alkoxy further comprising only one to the maximum possible number of identical or different halos, such as fluoromethoxy, trifluoromethoxy, 2,2-difluoropropoxy, chloromethoxy, trichloromethoxy, 1,1,2. , 2-Tetrafluoroethoxy and pentafluoroethoxy.

"Haloalkyl" is an alkyl that further comprises from one to the maximum possible number of identical or different halos, such as fluoromethyl, trifluoromethyl, 2,2-difluoropropyl, chloromethyl, trichloromethyl and 1,1,2,2. -Meaning tetrafluoroethyl.

"Heterocyclyl" means a cyclic substituent that may be fully saturated, partially unsaturated or completely unsaturated, where the cyclic structure is at least one carbon and at least one. It contains a heteroatom, wherein the heteroatom is nitrogen, sulfur or oxygen. Examples of aromatic heterocyclyls include benzofuranyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, benzothienyl, benzothiazolyl, cinnolinyl, furanyl, indazolyl, indrill, imidazolyl, isoindrill, isoquinolinyl, isothiazolyl, isooxazolyl, oxadiazolyl, Includes, but is not limited to, oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl, triazinyl and triazolyl. Examples of fully saturated heterocyclyls include, but are not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl, tetrahydrofuranyl and tetrahydropyranyl. Examples of partially unsaturated heterocyclyls include 1,2,3,4-tetrahydro-quinolinyl, 4,5-dihydro-oxazolyl, 4,5-dihydro-1H-pyrazolyl, 4,5-dihydro-isooxazolyl and 2,3-Dihydro- [1,3,4] -oxadiazolyl is included, but not limited to these.

Detailed Description of Disclosure This document describes molecules and N-oxides having the following formulas (“Formula 1” and / or “Formula 2”), agriculturally acceptable acid additions, salt derivatives, solvates, esters. Disclosed derivatives, polymorphs, isotopes, split steric isomers and / or tautomers,

During the ceremony:
(A) Ar ¹ is selected from (1) furanyl, phenyl, pyridadinyl, pyridyl, pyrimidinyl or thienyl or (2) substituted furanyl, substituted phenyl, substituted pyridadinyl, substituted pyridyl, substituted pyrimidinyl or substituted thienyl.
Here, the substituted furanyl, the substituted phenyl, the substituted pyridadinyl, the substituted pyridyl, the substituted pyrimidinyl and the substituted thienyl are H, F, Cl, Br, I, CN, NO ₂ , (C ₁ − C ₈ ) alkyl, (C ₁ −. C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) halo alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) alkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C1 _- C8) alkyl, C ₍ O) O- (C1 _- C8) alkyl, C ₍ O)-(C3 _- C8) cycloalkyl, C ₍ O) ) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl -O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl- It has one or more substituents independently selected from C (O) O- (C1 _- C ₈ ) alkyl, phenyl and phenoxy.
Here, each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl and phenoxy substituents are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ) alkyl, (C ₁ ). -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) haloalkoxy, (C ₂ -C ₈ ) alkoxy, (C ₂ -C ₈ ) ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C) ₁ -C ₈ ) haloalkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O -(C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) haloalkyl, C (O)-(C ₃ -C ₈ ) ) Cycloalkyl, C ₍ O) O- ₍ C3 _- C8) cycloalkyl, C ₍ O)-( _{C2 -} C8) alkoxy, C (O) O- (C2-C8) alkoxy, ( C1 _- C8) Alkoxy-O- (C1 _- C8) Alkoxy, ₍ C1 _- C8) Alkoxy-S ₍ O) _n- (C1 _- C8) Alkoxy, _{C (} O)-(C) It may be substituted with one or more substituents independently selected from the group consisting of ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl and phenoxy;
(B) Het is a 5- or 6-membered saturated or unsaturated heterocyclic ring containing one or more heteroatoms independently selected from nitrogen, sulfur or oxygen, where Ar ¹ and Ar. ² are not orthos to each other (but in the case of meta or para, they are 1,3 in the case of 5-membered rings and they are 1,3 or 1,4 in the case of 6-membered rings. And here the heterocyclic ring is also H, F, Cl, Br, I, CN, NO ₂ , oxo, (C1 _- C8) alkyl, ₍ C3 _- C8) cycloalkyl, ₍ C ₁ -C ₈ ) alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) ) Alkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) Alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) Alkyne, C (O) O- (C ₁ ) -C ₈ ) alkyl, C (O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl , C (O) O- (C2 _- C8) alkenyl, ₍ C1 _- C8) alkyl _- O- (C1 _- C8) alkyl, ₍ C1 _- C8) alkyl _- S (O) _n -Selected independently from the group consisting of (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl and phenoxy. May be substituted with one or more substituents
Here, each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl and phenoxy substituents are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ) alkyl, (C ₁ ). -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) haloalkoxy, (C ₂ -C ₈ ) alkoxy, (C ₂ -C ₈ ) ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C) ₁ -C ₈ ) Haloalkyl, C (O) -NR ^x R ^y ,
(C ₁ -C ₈ ) Alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) Alkyl, C (O) O- (C ₁ -C ₈ ) Alkyl, C (O)-(C) ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) haloalkyl, C (O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) Cycloalkyl, C (O)- ₍ C2 _- C8) alkenyl, C (O) O- (C2 _- C8) alkenyl, ₍ C1 _- C8) alkyl _- O- ₍ C1 _- C8) Alkyl, (C ₁ -C ₈ ) Alkyl-S (O) _n- (C ₁ -C ₈ ) Alkyl, C (O)-(C ₁ -C ₈ ) Alkyl-C (O) O- (C _1- ) C ₈ ) May be substituted with one or more substituents independently selected from the group consisting of alkyl, phenyl and phenoxy;
(C) Ar ² is selected from (1) furanyl, phenyl, pyridadinyl, pyridyl, pyrimidinyl or thienyl or (2) substituted furanyl, substituted phenyl, substituted pyridadinyl, substituted pyridyl, substituted pyrimidinyl or substituted thienyl, and here with Het. L are not ortho to each other (but in the case of meta or para, they are 1,3 in the case of 5-membered rings and they are 1,3 or 1,4 in the case of 6-membered rings. There is);
Here, the substituted furanyl, the substituted phenyl, the substituted pyridadinyl, the substituted pyridyl, the substituted pyrimidinyl and the substituted thienyl are H, F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ -C ₈ ) alkyl. , (C ₁ -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) halo alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) alkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) ) Alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C ₃ -C ₈ ) cyclo Alkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ ) -C ₈ ) Alkyl-O- (C ₁ -C ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-S (O) _n- (C ₁ -C ₈ ) Alkyl, C (O)-(C _1- ) C ₈ ) Alkyl-C (O) O- (C1-C ₈ ) It has _one or more substituents independently selected from alkyl, phenyl and phenoxy.
Here, each alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl, phenyl and phenoxy substituents are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ). Alkyne, (C1 _- C8) haloalkyl, ₍ C3 _- C8) cycloalkyl, ₍ C1 _- C8) alkoxy, (C1 _- C8) haloalkoxy, _{( C2 -} C8) alkoxy, (C2 _- C8) alkoxy, (C2-C8) C ₂ -C ₈ ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) Alkyl, S (O) _n- (C ₁ -C ₈ ) Haloalkyl, OSO _2- (C ₁ -C ₈ ) Alkoxy, OSO _2- (C ₁ -C ₈ ) haloalkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) haloalkyl, C (O)-( C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkoxy, C (O) O- (C ₂ -C) ₈ ) Alkoxy, (C ₁ -C ₈ ) Alkoxy-O- (C ₁ -C ₈ ) Alkoxy, (C ₁ -C ₈ ) Alkoxy-S (O) _n- (C ₁ -C ₈ ) Alkoxy, C ( O)-(C ₁ -C ₈ ) Alkoxy-C (O) O- (C ₁ -C ₈ ) Substituent with one or more substituents independently selected from the group consisting of alkyl, phenyl and phenoxy. May;
(D) L is selected from ( ₁ ) saturated or unsaturated, substituted linear (C1- _C4 ) hydrocarbyl linkers and (2) saturated or unsaturated, substituted cyclic ₍ C3 _- C8) hydrocarbyl group linkers. Linker
Here, each of the linkers links Ar ² to ^NY , and here the substituted linear (C ₁ -C ₄ ) hydrocarbyl linker and the substituted cyclic (C ₃ -C ₈ ) hydrocarbyl linker are R ⁸ ,. It has one or more substituents independently selected from R ⁹ , R ¹⁰ , R ¹¹ and R ¹² , where each R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and ^{R 12} are -NR AC ( O) ^-RB , -N
RAC (O) O ^- RB, -C ( ^O ) -OH or -C (O) O ^- RB selected from
Where ^RA is H or (C ₁ -C ₈ ) alkyl and RB is ( ^C ₁ -C ₈ ) alkyl or (C ₁ -C ₈ ) alkyl substituted with at least one phenyl. ;
(E) R ¹ is H, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n -(C ₁ -C ₈ ) alkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-OC (O)-(C ₁ -C ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-S (O) _n- (C ₁ -C ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-OC (O) O- (C ₁ -C ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-C (O) O- (C ₁ -C ₈ ) Alkyl, C (O) Alkyl, (C ₁ -C ₈ ) Alkyl-C (O)-(C ₁ -C ₈ ) ) Alkyl, (C ₁ -C ₈ ) alkyl phenyl, (C ₁ -C ₈ ) alkyl-O-phenyl selected from the group.
Here, each alkyl, cycloalkyl, alkenyl and alkynyl are optionally H, F, Cl, Br, I, CN, NO ₂ , oxo, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C3 _- C8) cycloalkyl, (C1 _- C8) alkoxy, ₍ C1 _- C8) haloalkoxy, _{( C2 -} C8) alkenyl, ₍ C2 _- C8) alkynyl, S ₍ O) ) _N- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) halo alkyl , C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C) ₈ ) Alkyl, C (O)-(C1 _- C8) haloalkyl, C ₍ O) O- (C1 _- C8) haloalkyl, C ₍ O)-(C3 _- C8) cycloalkyl, C ₍ O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) Alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl -C (O) O- (C ₁ -C ₈ ) may be substituted with one or more substituents independently selected from the group consisting of alkyl, phenyl and phenoxy;
(F) Q and Q ¹ are independently selected from the group consisting of O and S;
(G) R ² is (J), H, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, C (O)-(C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C) ₁ -C ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne phenyl, (C ₁ -C ₈ ) Alkyne-O-Phenyl, C (O)-(Het-1), (Het-1), (C ₁ ) -C ₈ ) Alkyne- (Het _{- 1} ), (C1-C ₈ ) Alkyne-OC (O)-(C1-C ₈ ) Alkyne, (C1 _- C ₈ ) Alkyne-OC (O) O- (C ₁ -C ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne-OC (O) -NR ^x R ^y , (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ ) -C ₈ ) Alkyne- (Het- ₁ ), (C1-C ₈ ) Alkyne-C (O)-(Het- ₁ ), (C1-C ₈ ) Alkyne-C (O) -N (R ^x ) ) (C ₁ -C ₈ ) Alkyne (NR ^x R ^y ) -C (O) OH, (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne- NR ^x R ^y , (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne-N (R ^x ) -C (O) O- (C ₁ -C) ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne (N (R ^x ) -C (O) O- (C ₁ -C ₈ ) ) Alkyl) -C (O) OH, (C ₁ -C ₈ ) Alkyl-C (O)-(Het-1) -C (O) O- (C ₁ -C ₈ ) Alkyne, (C ₁ -C 8) ₈ ) Alkyne-OC (O) O- (C1 _- C8) alkyl, ₍ C1 _- C8) alkyl _- OC (O)- ₍ C1 _- C8) alkyl, ₍ C1 _- C8) alkyl -OC (O)-(C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkyl-OC (O)-(Het-1), (C ₁ -C ₈ ) alkyl-OC (O)- (C ₁ -C ₈ ) Alkyne-N (R ^x ) -C (O) O- (C ₁ -C ₈ ) Alkyne, (C _1- Group consisting of C ₈ ) alkyl-NR ^x R ^y , (C1 _- C ₈ ) alkyl-S (O) _n- (Het- ₁ ) and (C1-C ₈ ) alkyl-O- (Het-1) Selected from
Here each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and (Het)
-1) is optionally H, F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₃ -C). ₈ ) Cycloalkyl, (C1-C8) alkoxy, _{( C2 -} C8) alkenyl, ₍ C2 _- C8) alkynyl, S ₍ O) _{n- (} C1 _- C8) alkyl, S (O) ) _N- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) haloalkyl, C (O) H, C (O) OH, C ( O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C ₈ ) alkyl , C (O)-(C1 _- C8) haloalkyl, C ₍ O) O- (C1 _- C8) haloalkyl, C ₍ O)-(C3 _- C8) cycloalkyl, C ₍ O) O -(C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O -(C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl-C ( O) From the group consisting of O- (C ₁ -C ₈ ) alkyl, phenyl, phenoxy, Si ((C ₁ -C ₈ ) alkyl) ₃ , S (O) _n -NR ^x R ^y and (Het-1). It may be substituted with one or more independently selected substituents;
(H) R ³ is (C ₃ -C ₈ ) cycloalkyl, phenyl, (C ₁ -C ₈ ) alkyl phenyl, (C ₁ -C ₈ ) alkyl-O-phenyl, (C ₂ -C ₈ ) alkenyl- Selected from the group consisting of O-phenyl, (Het- ₁ ), (C1 _- C8) alkyl- (Het- ₁ ) and (C1 _- C8) alkyl-O- (Het-1).
Here, each alkyl, cycloalkyl, alkenyl, phenyl and (Het-1) are optionally H, F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) halo alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ ) -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO ₂ -(C ₁ -C ₈ ) haloalkyl, C (O) H, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) Alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) halo alkyl, C ( O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₁ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- ( C ₂ -C ₈ ) alkenyl, O- (C ₁ -C ₈ ) alkyl, S- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, One or more independently selected from the group consisting of C (O)-(C ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl, phenoxy and (Het-1). May be substituted with a substituent of;
(I) R ⁴ is (J), H, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, C (O)-(C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C) ₁ -C ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne phenyl, (C ₁ -C ₈ ) Alkyne-O-Phenyl, C (O)-(Het-1), (Het-1), (C ₁ ) -C ₈ ) Alkyne- (Het _{- 1} ), (C1-C ₈ ) Alkyne-OC (O)-(C1-C ₈ ) Alkyne, (C1 _- C ₈ ) Alkyne-OC (O) O- (C ₁ -C ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne-OC (O) -NR ^x R ^y , (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ ) -C ₈ ) Alkyne- (Het- ₁ ), (C1-C ₈ ) Alkyne-C (O)-(Het- ₁ ), (C1-C ₈ ) Alkyne-C (O) -N (R ^x ) ) (C ₁ -C ₈ ) Alkyne (NR ^x R ^y ) -C (O) OH, (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne- NR ^x R ^y , (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne-N (R ^x ) -C (O) O- (C ₁ -C) ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne (N (R ^x ) -C (O) O- (C ₁ -C ₈ ) ) Alkyl) -C (O) OH, (C ₁ -C ₈ ) Alkyl-C (O)-(Het-1) -C (O) O- (C ₁ -C ₈ ) Alkyne, (C ₁ -C 8) ₈ ) Alkyne-OC (O) O- (C1 _- C8) alkyl, ₍ C1 _- C8) alkyl _- OC (O)- ₍ C1 _- C8) alkyl, ₍ C1 _- C8) alkyl -OC (O)-(C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkyl-OC (O)-(Het-1), (C ₁ -C ₈ ) alkyl-OC (O)- (C ₁ -C ₈ )
Alkyl-N (R ^x ) -C (O) O- (C ₁ -C ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-NR ^x R ^y , (C ₁ -C ₈ ) Alkyl-S (O) Selected from the group consisting of _n- (Het- ₁ ) and (C1 _- C8) alkyl-O- (Het-1).
Here, each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and (Het-1) are optionally H, F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ -C ₈ ). Alkyl, (C1 _- C8) haloalkyl, ₍ C3 _- C8) cycloalkyl, (C1 _- C8) alkoxy, _{( C2 -} C8) alkenyl, ₍ C2 _- C8) alkynyl, S ₍ O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) Haloalkyl, C (O) H, C (O) OH, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) Alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) Alkyl, C (O) O- (C1 _- C8) alkyl, C ₍ O)-(C1 _- C8) haloalkyl, C ₍ O) O- (C1 _- C8) haloalkyl, C ₍ O) -(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ ) -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl, phenoxy, Si ((C ₁ -C ₈ ) alkyl) ₃ , S (O) It may be substituted with one or more substituents independently selected from the group consisting of _n -NR ^x R ^y and (Het-1);
(J) R ² and R ⁴ may be combined with C ^X (Q ¹ ) ( ^NX ) to form 4- to 7-membered saturated or unsaturated heterocyclic rings, which are further nitrogen, It may contain one or more heteroatoms selected from the group consisting of sulfur and oxygen, where each heterocyclic ring is optionally independently selected from the group consisting of R ⁵ , R ⁶ and R ⁷ . It may be substituted with one or more substituents,
Here, R ⁵ , R ⁶ and R ⁷ are independently H, F, Cl, Br, I, CN, OH, NO ₂ , NR ^x R ^y , oxo, tioxo, (C ₁ -C ₈ ) alkyl, respectively. (C ₁ -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) halo alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ ) -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO ₂ -(C ₁ -C ₈ ) haloalkyl, C (O) H, C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)- (C1 _- C8) haloalkyl, C ₍ O) O- (C1 _- C8) haloalkyl, C ₍ O)-(C3 _- C8) cycloalkyl, C ₍ O) O- (C3 _- C) ₈ ) Cycloalkyl, C (O)- ₍ C2 _- C8) alkenyl, C (O) O- ₍ C2 _- C8) alkenyl, (C1 _- C8) Alkyl _- O- (C1 _- C) ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-S (O) _n- (C ₁ -C ₈ ) Alkyl, C (O)-(C ₁ -C ₈ ) Alkyl-C (O) O- (C) ₁ -C ₈ ) Selected from the group consisting of alkyl, phenyl and (Het-1);
(K) R ^x and R ^y are independently H, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₂ -C ₈ ). Alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) alkyl, C (O) H, C (O)-( C1 _- C8) alkyl, C ₍ O) O- (C1 _- C8) alkyl, C ₍ O)-(C3 _- C8) cycloalkyl, C ₍ O) O- ₍ C3 _- C8) ) Cycloalkyl, C (O)- ₍ C2 _- C8) alkenyl, C (O) O- (C2 _- C8) alkenyl, ₍ C1 _- C8) alkyl _- O- ₍ C1 _- C8) ) Alkyl, (C ₁ -C ₈ ) Alkyl-S (O) _n- (C ₁ -C ₈ ) Alkyl, C (O)-(C ₁ -C ₈ ) Alkyl-C (O) O- (C ₁ ) Selected from the group consisting of -C ₈ ) alkyl, phenyl and (C ₁ -C ₈ ) alkyl phenyl.
Here, each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl and alkylphenyl are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ) alkyl, (C _1- ). C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) haloalkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) Alkoxyyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ ) -C ₈ ) Haloalkyl, C (O) H, C (O)
-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C) ₈ ) Haloalkyl, C (O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- ( Independent from the group consisting of C1 _- C8) alkyl, C ₍ O)-(C1 _- C8) alkyl-C ₍ O) O- ₍ C1 _- C8) alkyl, phenyl and (Het-1) May be substituted with one or more substituents selected;
(L) (Het-1) is a 5- or 6-membered saturated or unsaturated heterocyclic ring containing one or more heteroatoms independently selected from nitrogen, sulfur or oxygen.
Here, the heterocyclic ring is optionally H, F, Cl, Br, I, CN, NO ₂ , oxo, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ ). -C ₈ ) alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) alkyl , C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C) ₈ ) Alkyl, C (O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- ( Independently selected from the group consisting of C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl and phenoxy 1 May be substituted with more than one substituent,
Here, each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl and phenoxy substituents are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ) alkyl, (C ₁ ). -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) haloalkoxy, (C ₂ -C ₈ ) alkoxy, (C ₂ -C ₈ ) ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C) ₁ -C ₈ ) haloalkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O -(C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) haloalkyl, C (O)-(C ₃ -C ₈ ) ) Cycloalkyl, C ₍ O) O- ₍ C3 _- C8) cycloalkyl, C ₍ O)-( _{C2 -} C8) alkoxy, C (O) O- (C2-C8) alkoxy, ( C1 _- C8) Alkoxy-O- (C1 _- C8) Alkoxy, ₍ C1 _- C8) Alkoxy-S ₍ O) _n- (C1 _- C8) Alkoxy, _{C (} O)-(C) It may be substituted with one or more substituents independently selected from the group consisting of ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl and phenoxy;
(M) n is 0, 1 or 2, respectively.

For the avoidance of doubt, the designations ^NX and ^NY refer to the usual nitrogen atoms at specific positions set forth in Equations 1 and 2. Similarly, the C ^X designation refers to a normal carbon atom at a particular position as set forth in Equations 1 and 2.

In one embodiment, Ar ¹ is a substituted phenyl. This embodiment may be used in combination with other embodiments of Het, Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or L.

In another embodiment, Ar ¹ is a substituted phenyl having one or more substituents selected from C ₁ -C ₆ haloalkyl and C ₁ -C ₆ haloalkoxy. This embodiment may be used in combination with other embodiments of Het, Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or L.

In another embodiment, Ar ¹ is a substituted phenyl having one or more substituents selected from CF ₃ , OCF ₃ and OC ₂ F ₅ . This aspect is Het, Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q,
May be used in combination with Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other aspects of L.

In another embodiment, Het is benzofuranyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, benzothienyl, benzothiazolyl, cinnolinyl, furanyl, indazolyl, indolyl, imidazolyl, isoindolyl, isoquinolinyl, isothiazolyl, isooxazolyl, oxadiazolyl, Oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl, pyridadinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl, triazinyl, triazolyl, piperazinyl, piperidinyl Pyranyl, 1,2,3,4-tetrahydro-quinolinyl, 4,5-dihydro-oxazolyl, 4,5-dihydro-1H-pyrazolyl, 4,5-dihydro-isooxazolyl and 2,3-dihydro- [1, 3,4] -Selected from oxadiazolyl.

In another embodiment, Het is triazolyl. This embodiment may be used in combination with Ar ¹ , Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L. ..

In another embodiment, Het is 1,2,4-triazolyl. This embodiment may be used in combination with Ar ¹ , Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L. ..

In another embodiment, Het is oxadiazolyl. This embodiment may be used in combination with Ar ¹ , Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L. ..

In another embodiment, Het is 1,3,4-oxadiazolyl. This embodiment may be used in combination with Ar ¹ , Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L. ..

In another embodiment, Het is pyrazolyl. This embodiment may be used in combination with Ar ¹ , Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L. ..

In another embodiment, Ar ² is phenyl. This embodiment may be used in combination with Ar ¹ , Het, R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, Ar ² is a substituted phenyl. This embodiment may be used in combination with Ar ¹ , Het, R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, Ar ² is a substituted phenyl with one or more substituents selected from C ₁ -C ₆ alkyl. This embodiment may be used in combination with Ar ¹ , Het, R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, Ar ² is a substituted phenyl having one or more substituents, wherein the substituent is CH ₃ . This aspect is Ar ¹ , Het, R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ , R ²
And R ⁴ hydrocarbyl links and / or may be used in combination with other aspects of L.

In another embodiment, R ¹ is H. This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ² , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ² is (J), H, (C ₁ -C ₆ ) alkyl, (C ₁ -C ₆ ) alkyl-OC (O)-(C ₁ -C ₆ ) alkyl, (C 1-C 6) alkyl. ₁ -C ₆ ) Alkyl-OC (O) -N (R ^x R ^y ) or (C ₁ -C ₆ Alkyl) -S- (Het-1). This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ¹ , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ² is (J), H, CH ₃ , (C1 _- C ₆ ) alkyl, CH ₂ OC (O) CH (CH ₃ ) ₂ , CH ₂ OC (O) N (H) ( C (O) OCH ₂ Ph) or CH ₂ S (3,4,5-trimethoxy-2-tetrahydropyran). This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ¹ , R ³ , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ³ is substituted phenyl. This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ¹ , R ² , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ³ is a substituted phenyl, where the substituted phenyl is F, Cl, (C ₁ -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl, (C ₁ -C ₆ ) alkoxy. And has one or more substituents selected from phenyl. This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ¹ , R ² , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ³ is a substituted phenyl, wherein the substituted phenyl is from F, CH ₃ , 2-CH (CH ₃ ) ₂ , CH (CH ₃ ) (C ₂ H ₅ ), OCH ₃ and phenyl. It has one or more substituents of choice. This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ¹ , R ² , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ³ is a substituted phenyl, where the substituted phenyl has more than one substituent and at least one pair of the substituents is not ortho to each other. This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ¹ , R ² , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ³ is (C1 _- C ₆ ) alkylphenyl. This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ¹ , R ² , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ³ is (Het-1). This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ¹ , R ² , R ⁴ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ⁴ is H. This embodiment may be used in combination with Ar ¹ , Het, Ar ² , R ¹ , R ² , R ³ , Q, Q ¹ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, Q is O. This embodiment may be used in combination with Ar ¹ , Het, Ar ² , Q ¹ , R ¹ , R ² , R ³ , R ⁴ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L. ..

In another embodiment, Q ¹ is O. This embodiment may be used in combination with Ar ¹ , Het, Ar ² , Q, R ¹ , R ² , R ³ , R ⁴ , R ² and R ⁴ hydrocarbyl links and / or other embodiments of L.

In another embodiment, R ² and R ⁴ are hydrocarbyl links, where the hydrocarbyl link is substituted with oxo or (C1 _- C ₆ ) alkyl. This embodiment may be used in combination with other aspects of Ar ¹ , Het, Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ and / or L.

In another embodiment, R ² and R ⁴ are hydrocarbyl links, where the hydrocarbyl links are CH ₂ C (O), C (C (OH) (CH ₃ ) ₂ ) C (O), C (cyclopropyl). ) C (O), C (CH ₃ ) ₂ C (O), CFHC (O), CBrHC (O), CH (CH ₃ ) C (O), CH ₂ CH ₂ , CH ₂ C (OH) (CH) ₃ ), CH ₂ CH ₂ CH ₂ , CH ₂ CH ₂ C (O), CH ₂ CH (CH ₃ ) CH ₂ , N (CH ₃ ) C (O), N (CH ₂ CH ₃ ) C (O) , CH = C (CH ₃ ) or CH ₂ CH (CH ₃ ). This embodiment may be used in combination with other aspects of Ar ¹ , Het, Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ and / or L.

In another embodiment, L is CH ₂ , CH ₂ CH ₂ , CH ₂ CH (CH ₃ ), CH ₂ C (CH ₃ ) ₂ , CH ₂ CH (CH ₂ CH ₃ ), CH = CH, CH (CH ₃ ). ) CH ₂ , C (CH ₃ ) ₂ CH ₂ , CHBrCH ₂ , CH ₂ C (cyclopropyl), CH (CH ₂ CH ₃ ) CH ₂ , C (CH ₃ ) = CH, CH ₂ CH ₂ CH ₂ , CH (CH ₃ ) CH (CH ₃ ), CH ₂ CH ₂ CH ₂ CH ₂ , C≡CCH ₂ CH ₂ , cycloprolopill or cyclohexyl. This embodiment may be used in combination with other embodiments of Ar ¹ , Het, Ar ² , R ¹ , R ² , R ³ , R ⁴ , Q, Q ¹ and / or R ² and R ⁴ hydrocarbyl links. ..

Many of the molecules of formulas 1 and 2 may be represented in two or more tautomeric forms, such as when R ¹ , R ² or R ⁴ is H. All alternative tautomers are included within this formula 1 and this formula 2 and inferences are made as to whether the molecule exists as the tautomer form in which it is depicted. Should not be.

Preparation of Triaryl-Intermediate The molecules of formulas 1 and 2 are formed by forming the triaryl intermediate, Ar ¹ -Het-Ar ² , and then linking it to a suitable intermediate to form the desired compound. Can be manufactured. A variety of triaryl intermediates can be used for the preparation of the molecules of formulas 1 and 2, provided that such triaryl intermediates have suitable functional groups to which the rest of the desired functional groups can be attached. It is contained on Ar ² . Suitable functional groups include amino, isocyanate, carboxyl or halogen (preferably bromo or iodine). These triaryl intermediates are described in Clause et al. , International Publication No. 2009102736 (the entire disclosure of which is hereby incorporated by reference) can be produced by the methods previously described in the chemical literature.

Triaryl aldehydes used as precursors in the production of the molecules of formulas 1 and 2 are described in Clause et al. , U.S. Pat. No. 2012/2026888A1 can be manufactured according to the method described in the specification. Some of the above methods require the use of halo-aryl intermediates, Ar ¹ -Het-Ph-Br, which are novel intermediates. These may be manufactured as described in Scheme 1 below. 3- (4-Bromophenyl) -1,2,4-triazole (1-2) is prepared from 4-bromobenzamide (1-1) under the conditions previously described (step a, Clause). et al., International Publication No. 2009102736 (Pamphlet). This triazole is then subjected to aryl halide 1-3 (R =) such as 4-trifluoromethoxyphenylbromobenzene in a polar aprotic solvent such as N, N-dimethylformamide in the presence of cesium carbonate or potassium phosphate. It can be coupled to (C1 _- C6) _haloalkoxy ). This reaction is like copper salts like copper (I) iodide and 8-hydroxyquinoline, both present at temperatures ranging from about 80 ° C to about 140 ° C and both at about 0.05 to about 0.25 equivalents. It is catalyzed by a suitable chelating agent to form 1-aryl-3- (4-bromophenyl) triazole 1-4 (step b).

Preparation of 1-Atomic Linkage Intermediate Molecules of Formula 1 and Formula 2 in which L is a 1-carbon linker can be prepared from the acid or amine intermediates described in Scheme 2 and Scheme 3, respectively. The acid precursor 2-5 (Ar ¹ -Het-Ar ² -L-CO ₂ H) which is unsubstituted or mono- or 2-substituted with R ⁸ can be produced as shown in Scheme 2. can. Boronic acid ester 2-2 (step a) can be prepared from halophenyl ester 2-1 using Miyaura conditions. Using a palladium catalyst and a phosphine ligand at a temperature of about 50 ° C to about 120 ° C in a suitable solvent system such as dioxane / water in the presence of a base such as sodium bicarbonate, potassium phosphate or cesium fluoride. Coupling of the boronate ester with the bromo-heterocycle 2-3 (step b) can be performed to form the triaryl ester intermediate 2-4. Among the palladium catalysts, tetrakis (triphenylphosphine) palladium (0) is preferable, but other well-known palladium catalysts may be used. The ester may be saponified by using a strong base such as sodium hydroxide or lithium hydroxide in methanol or ethanol with or without tetrahydrofuran / water to give the desired carboxylic acid 2-5 (step). c).

The amine precursor 3-5 (Ar ¹ -Het-Ar ² -L-NH ₂ ) which is unsubstituted or mono- or 2-substituted with R ⁸ can be produced as shown in Scheme 3. Protecting halobenzylamine 3-1 with benzyl chloroformate at a temperature of about -10 ° C to about 10 ° C in an aprotic solvent such as dichloromethane in the presence of a base such as triethylamine, N-carboxy Benzyl (Cbz) -protected benzylamine 3-2 may be given (step a). Alternatively, in step a, other N-protecting groups such as tert-butoxycarbonyl (BOC) or 9-fluorenylmethyloxycarbonyl (Fmoc) are used with conditions similar to those described above for Cbz. May be. The Cbz-protected boronic acid ester 3-3 can be prepared using the Miyaura condition (step b). Using a palladium catalyst and a phosphine ligand at a temperature of about 50 ° C to about 120 ° C in a suitable solvent system such as dioxane / water in the presence of a base such as sodium bicarbonate, potassium phosphate or cesium fluoride. Coupling of the boronate ester with the bromo-heterocycle 2-3 can be performed to form the N-protected aminoalkylphenyl intermediate 3-4 (step c). Under acidic conditions, the Cbz group is removed with a strong acid such as hydrogen bromide, followed by neutralization with a base such as sodium bicarbonate or sodium hydroxide, free amine precursor 3-5 ( Ar ¹ -Het-Ar ² -L-NH ₂ , step d) can be given. Similar methods can be applied to compounds with L longer than 1-carbon.

Production of Ethyl Linked Intermediate The production of compounds in which L is a 2-atomic group is described in Schemes 4-6. Like ethyl diethylphosphonoacetate at a temperature of about -78 ° C to about 20 ° C in an aprotonic solvent such as tetrahydrofuran or diethyl ether in the presence of a suitable base such as sodium hydride or n-butyl lithium. Reagents or Wittig reagents such as ethyl 2- (triphenylphosphoraniliden) propanoate or α-substituted acetates such as ethyl 2-fluoroacetate or ethyl 2-cyanoacetate aldehyde 4-1 (R ⁹ = H). Acrylic ester 4-2 (step a) that is unsubstituted or mono-substituted with R ⁹ and / or R ¹⁰ using the condensation of (described in US Pat. No. 2012/0202688A1). Can be manufactured. Saponification of the resulting ester may be carried out in methanol or ethanol with or without tetrahydrofuran / water using a strong base such as sodium hydroxide to give vinylcarboxylic acid 4-3 (step b). .. In some cases partial condensation of the aldehyde 4-1 (R ⁹ = H) results in the isolation of the alcohol intermediate 4-4 (step c), especially if R ¹⁰ is electron-withdrawing. There is. Substitution of this alcohol using a nucleophile such as Deoxo-Fluor® (step d) followed by saponification as described above (step e) was further substituted with R ¹¹ and highly substituted ethyl carboxylic acid. Acids 4-5 can be produced, where R ¹¹ is defined similarly to R ⁸ above. If saturated linkage is preferred, use sulfur ylides such as those produced in situ from trimethylsulfonium iodide in the presence of inorganic bases such as sodium hydride in polar aprotic solvents such as dimethyl sulfoxide or tetrahydrofuran. , Acrylic acid ester 4-2 can be converted to the corresponding cyclopropane 4-6 which is unsubstituted or mono- or 2-substituted with R ¹² (step f). Similarly, hydrogen gas and palladium catalysts can be used to reduce the acrylic acid ester 4-2 to the parent alkane 4-8 (step h). Both cyclopropane and alkane esters can be saponified under the basic conditions described above to produce free carboxylic acids 4-7 (step g) and 4-9 (step i), respectively.

Wittig reagents such as ethyl diethylphosphonoacetate or ethyl 2- (triphenylphosphoraniliden) propanoate or such as ethyl 2-fluoroacetate or ethyl 2-cyanoacetate in a similar manner and under similar conditions as above. Condensation of the ketone 4-1 (R ⁹ = alkyl) (described in US Pat. No. 2014,107,504A1) using an α-substituted alkyl ester comprises the α-alkyl acrylate ester 4-2 or alcohol 4-2. May be given. Subsequent treatments of 4-2 or 4-2 as described above for R ⁹ = H will result in the corresponding unsaturated (4-3) or saturated (4-5, 4-7, 4-9) carboxylic acid. May lead.

Alternatively, a compound in which L is a 2-carbon linker may be prepared as shown in Scheme 5. First, Molander et al. Org. Let. Bromide 5-1 at a temperature of about 80 ° C to about 120 ° C in the presence of a palladium catalyst such as palladium (II) acetate and a base such as cesium carbonate, using the conditions described in 2007, 9, pp203-206. Coupling (Ar ¹ -Het-Ar ² -Br, step a) with (2-((tert-butoxycarbonyl) amino) ethyl) potassium trifluororoborate gives the corresponding 2- (tert-butoxycarbonyl). Amino) Produces the formation of ethyl derivative 5-2. Further treatment of this material in an aprotic solvent such as dichloromethane or dioxane at a temperature of about 0 ° C to about 50 ° C with about 1 to about 5 equivalents of an acid such as trifluoroacetic acid (TFA) or hydrogen chloride Cleavage of tert-butoxycarbonyl group and salt of amine 5-3 (Ar ¹ -Het-Ar ² -L-NH ₃ ⁺ A-, where A ^- is CF ₃ CO ₂ ⁼ or ^{Cl- ,} step b) Produces the generation of.

L is a 2-carbon atom and is 1- or 2-replaced with R ⁹ , where R ⁹ is defined as above; and is unsubstituted or 1-substituted with R ¹⁰ . Here, R ¹⁰ can produce the aminoalkyl precursor 6-5 (Ar ¹ -Het-Ar ² -L-NH ₂ ) as defined above as shown in Scheme 6. Unsubstituted halophenylcarbinol 6-1 (R ⁹ and R ¹⁰ are H) in which X can be selected from Cl, Br or I are commercially available. The one- or two-substituted carbinol 6-1 in R ⁹ is from the corresponding halophenyl acetate 6-1 (step a), Shin et al. Bioorg. Med. Chem. Let. Using a method similar to the method described by 2008, 18, pp4424-4427 and subsequent metal hydrides such as lithium aluminum hydride in an ethereal solvent such as tetrahydrofuran or diethyl ether at temperatures below about 0 ° C. Can be manufactured by reduction. Both 6-1 and 6-11 were reduced to the corresponding aldehydes using metal hydrides such as diisobutylaluminum hydride, and further Brimble et al. Org. Let. It may be further mono-substituted with R ¹⁰ via treatment with Grignard reagents in a manner similar to the method described by 2012, 14, pp5820-5823 (step b or step c). Carbinol 6-1 can be treated with phthalimide under MeOH conditions to produce N-phthalimide intermediate 6-2 (step d). Halides can be converted to boronic acid esters under Miyaura conditions to form boronate ester 6-3 (step e). A palladium catalyst such as tetrakis (triphenylphosphine) palladium (0) at a temperature of about 50 ° C to about 120 ° C in the presence of a base such as sodium bicarbonate in a suitable solvent system such as dioxane / water. Can be used to couple the boronate ester to the bromo-heterocycle 2-3 to give the N-phthalimide intermediate 6-4 (step f). Deprotection with hydrazine and methanol or other suitable solvent can give amine 6-5 (step g).

Alternatively, compounds in which L is a 2-atomic linker may be prepared as shown in Scheme 6a. Methyl in an aprotic solvent such as tetrahydrofuran or dichloromethane at a temperature of about -78 ° C to about 40 ° C in the presence of a base such as sodium hydride or 1,8-diazabicycloundece-7-ene. Methylenetriphenylphosphoran, which can be produced from triphenylphosphonium iodide, may be used to olefinate aldehyde 4-1 (R ⁹ = H, step a). Hydroboration of 6-2a with a reagent such as 9-borabicyclo (3.3.1) nonane (9-BBN) in an aprotic solvent such as tetrahydrofuran followed by an oxidizing agent such as hydrogen peroxide. The oxidation used can produce ethyl alcohol 6-3a (step b). Carbinol 6-3a can be treated with phthalimide under MeOH conditions to produce the N-phthalimide intermediate 6-5a with R ¹⁰ = H (step c). Deprotection with hydrazine and methanol or other suitable solvent can give amine 6-6a (step f). In addition, 6-3a may be further mono-substituted with R ¹⁰ via oxidation to the corresponding aldehyde under Swern conditions and subsequent addition of the Grignard reagent as described above (Scheme 6), where R ¹⁰ Is defined as described above (step d). Carbinol 6-4a can be further treated with phthalimide under MeOH conditions to produce the N-phthalimide intermediate 6-5a (step e). Deprotection with hydrazine and methanol or other suitable solvent can give amine 6-6a (step f).

Scheme 6b outlines another pathway for the construction of analogs in which the linker L is a 2-atomic linker. Copper-catalyzed arylation of 2,4-pentane-2,4-dione using 5-1 (J. Am. Chem. Soc. 2010, 132, 8273) may provide substituted acetone intermediate 6-1b. (Step a). Reductive amination (step b) using any of the various conditions that one of ordinary skill in the art is accustomed to may produce amine 6-2b. If the linker contains a chiral center, as in the case of Intermediate 6-2b, either by using a chiral column or by fractional crystallization of salts made from chiral acids such as (+)-and (-)-tartaric acid. These intermediates may be separated into their pure isomers.

Construction of analogs in which the ethyl linking group is part of the 6-membered ring may also be carried out starting from bromide 5-1. The coupling of 5-1 and 2-cyclohexe-1-enyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane under standard Suzuki coupling conditions (Scheme 6b, step c) It can lead to Alken 6-3b. Epoxidation with standard reagents such as meta-chloroperoxybenzoic acid (step d) followed by acid-catalyzed rearrangement with indium trichloride (J. Org. Chem. 1998, 63, 8212) is a ketone 6-5b. May be generated. Reductive amination and conversion to the target molecule can be performed using the above conditions.

Preparation of Propyl Linked Intermediate The preparation of compounds in which L is a 3-atomic group is described in Schemes 7 and 8. L is a 3-carbon atom and is 1- or 2-replaced with R ⁹ , where R ⁹ is defined as above; and is unsubstituted or 1-substituted with R ¹⁰ . Here, R ¹⁰ can produce the aminoalkyl precursor 7-5 (Ar ¹ -Het-Ar ² -L-NH ₂ ) as defined above as shown in Scheme 7. Halophenylcarbinol 7-1 with X being Br and R ⁹ and R ¹⁰ being H is commercially available. The one- or two-substituted carbinol 7-1 in R ⁹ is from the corresponding halophenyl acetate 7-1 (step a), Shin et al. Bioorg. Med. Chem. Let. Produced by a method similar to the method described by 2008, 18, pp4424-4427, followed by reduction with a metal hydride such as lithium aluminum hydride in an ethereal solvent such as tetrahydrofuran at temperatures below about 0 ° C. Can be done. Both 7-1 and 7-11 were reduced to the corresponding aldehydes using metal hydrides such as diisobutylaluminum hydride to Brimble et al. Org. Let. It may be further mono-substituted with R ¹⁰ via treatment with Grignard reagents such as methylmagnesium bromide in a manner similar to the method described by 2012, 14, pp5820-5823 (step b or Step c). Carbinol 7-1 can be treated with phthalimide under MeOH conditions to produce N-phthalimide intermediate 7-2 (step d).

The halide can be converted under Miyaura conditions to form the boronate ester 7-3 (step e). Boronate using a palladium catalyst, such as tetrakis (triphenylphosphine) palladium (0), at a temperature of about 50 ° C to about 120 ° C in the presence of a base, such as sodium bicarbonate, in a suitable solvent system, such as dioxane / water. Coupling of the ester with the bromo-heterocycle 2-3 can be carried out to give the N-phthalimide intermediate 7-4 (step f). Deprotection with hydrazine and methanol or other suitable solvent can give amine 7-5 (step g).

Alternatively, compounds in which L is a 3-atomic linker may be prepared as shown in Scheme 8. Bromide 5-1 (Ar ¹ -Het-Ar ² -Br) at about 50 ° C. in the presence of a palladium catalyst such as bistriphenylphosphine palladium (II) dichloride, bases such as copper (I) iodide and triethylamine. It is unsubstituted or mono-substituted with R ¹⁰ at a temperature of ~ 120 ° C., where R ¹⁰ is coupled and corresponds to a suitable alkynyl alcohol 8-1 as defined above. The alkynyl alcohol derivative 8-2 can be produced (step a). The resulting carbinol 8-2 is treated with phthalimide under Mitsunobu conditions to produce the N-phthalimide intermediate 8-3 (step b), which is then used with hydrazine and methanol or other suitable solvent as amine 8- It can be converted to 7 (step e). Carbinol 8-2 can be reduced under atmospheric pressure hydrogen with a transition metal catalyst such as palladium to give an unsubstituted alkenyl at R ¹⁰ or a fully saturated alkyl carbinol 8-4. Further, carbinol 8-2 can be treated with a metal hydride such as lithium aluminum hydride to give (E) -alkenylcarbinol 8-4. Similarly, carbinol 8-2 is protected with a group such as tert-butyldiphenylsilyl (TBDPS) and treated with a hydrometallation reagent such as Schwartz's reagent, followed by elemental iodine or N-. Quenching may be done with an electrophile such as bromosuccinimide (NBS). Alternatively, it is further used in transition metal-catalyzed reactions such as Suzuki or Negishi coupling and is mono- or 2-substituted with R ⁹ , where R ⁹ is carbinol as defined above. In order to produce 8-4 (step c), carbinol 8-2 may be treated with a metal exchange reaction reagent such as pinacol diboron. Following deprotection, the resulting carbinol 8-4 can be treated with phthalimide under MeOH conditions to produce the N-phthalimide intermediate 8-5 (step d), which corresponds to the amine 8- Can be converted to 6.

Preparation of Butyl Linked Intermediate Compounds in which L is a 4-atomic linker may be prepared as shown in Scheme 9. Bromide 5-1 (Ar ¹ -Het-Ar ² -Br) at about 50 ° C. in the presence of a palladium catalyst such as bistriphenylphosphine palladium (II) dichloride, bases such as copper (I) iodide and triethylamine. At a temperature of ~ about 120 ° C., R ¹⁰ is unsubstituted or mono-substituted, where R ¹⁰ is defined as above and is 1- or 2--substituted with R ⁹ . R ⁹ can be coupled with a suitable alkynyl alcohol 9-1 as defined above to produce the corresponding alkynyl alcohol derivative 9-2 (step a). The resulting carbinol 9-2 is treated with phthalimide under Mitsunobu conditions to produce N-phthalimide intermediate 9-3 (step b), which is then used with hydrazine and methanol or other suitable solvent as amine 9-. It can be converted to 7 (step e). Carbinol 9-2 can be reduced under atmospheric pressure hydrogen with a transition metal catalyst such as palladium to give an unsubstituted alkenyl at R ¹³ or a fully saturated alkyl carbinol 9-4 (step). c). Further, carbinol 9-2 can be treated with a metal hydride such as lithium aluminum hydride to give (E) -alkenylcarbinol 9-4 (step c). Similarly, carbinol 9-2 is protected with a group such as tert-butyldiphenylsilyl (TBDPS) and treated with a hydrometalation reagent such as Schwartz's reagent, followed by an element of iodine or an electrophile such as NBS. Quenching may be performed using electronic reagents. Alternatively, it is further used in transition metal-catalyzed reactions such as Suzuki or Negishi coupling, where it is mono- or 2-substituted with R ¹³ , where R ¹³ is defined as R ⁸ above. In order to produce the carbinol 9-4 (step c), the carbinol 9-2 may be treated with a metal exchange reaction reagent such as pinacol diboron.

Following deprotection, the resulting carbinol 9-4 can be treated with phthalimide under Mitsunobu conditions to produce the N-phthalimide intermediate 9-5 (step d), which can be hydrazine and methanol or the like. Can be converted to amine 9-6 using a suitable solvent of (step e).

Production of N-arylthiazolidinone thiourea N-arylthiazolidinone thiourea (eg 10-4) by reacting thiazolidinone imine (eg 10-3) with triarylisothiocyanate (eg 10-2). Can be manufactured. As shown in Scheme 10, triarylisothiocyanates can be made from known fluoroamine intermediates (US Pat. No. 9,029,560).
From the specification of B2, for example, 10-1).

Triarylethyl isothiocyanate compound 11-3 can be prepared from triarylethylamine salt compound 11-2 using carbon disulfide in the presence of triethylamine and tosyl chloride in tetrahydrofuran (THF). As shown in Scheme 11, the amine salt 11-1 is after deprotection from the triarylbromid compound using TFA in Suzuki coupling with BOC-protected tert-ethylamine potassium fluoroborate and in dichloromethane. Occurs.

As shown in schemes 12a and 12b, intermediates 12-1 and 12-2 are synthesized and then used to produce the carbamate and ester N-arylthiazolidinone urea (or thiourea) 12-3 and 12-4. Can be done.

Benzaldehyde 12a-1 and 2-((tert-butoxycarbonyl) amino) -2- (at room temperature in the presence of a base such as 1,8-diazabicyclo [5.4.0] undeceth-7-ene (DBU)) Horner-Wadsworth of Wittig olefination between phosphonate esters such as dimethoxyphosphoryl) methyl acetate (12a-2)
Important intermediate 12a-4 can be produced via Emmons modification. Reduction of alkenes via hydrogenation on transition metal catalysts such as palladium carbon can give saturated intermediate 12a-4. The acid 12-1 can be obtained by saponifying the ester on 12a-4 with a base such as lithium hydroxide at room temperature to 50 ° C. in a mixture of polar solvents such as tetrahydrofuran, methanol and water. .. Reduction of 12a-4 with a strong acid such as hydrochloric acid in an aprotic solvent such as dichloromethane at room temperature can give the amine salt 12-2. Carbamate 12-3 is derived from acid 12-1 with diphenylphosphoryl azide and 2-imino-3- (2) at room temperature to about 60 ° C. in an aprotic solvent such as toluene in the presence of a base such as triethylamine. It can be produced by treatment with -isopropyl-5-methylphenyl) thiazolidine-4-one. Ester 12-4 is from the amine salt 12-2 in the presence of a base such as sodium bicarbonate in a two-phase solvent mixture such as dichloromethane-water at 0 ° C., triphosgene and 2-imino-3- (2-imino-3- (2-). It can be produced by treatment with isopropyl-5-methylphenyl) thiazolidine-4-one.

Examples These examples are for illustrative purposes only and should not be considered limiting this disclosure to the embodiments disclosed in these examples.

Starting materials, reagents and solvents from commercial sources were used without further purification. Anhydrous solvent was purchased from Aldrich as Sure / Seal ^TM and used as received. Thomas Hoover Unimelt Capillary Melting Point Device or Stanford
Obtain a melting point on the OptiMelt Automated Melting Point System from the Research Systems and do not modify it. Examples using "room temperature" were performed in a climate controlled laboratory using temperatures in the range of about 20 ° C to about 24 ° C. Molecules are given their known names, named according to the naming program within Symyx Draw, ChemDraw or ACD Name Pro. If such a program cannot name a molecule, the molecule is named using the usual naming convention. Unless otherwise stated, ^{1 1} H NMR spectral data is data in ppm (δ) and is recorded at 300, 400 or 600 MHz and ¹³ C NMR spectral data is data in ppm (δ) and is 75, 100 or Recorded at 150 MHz.

Example 1: (Z) -2-((tert-butoxycarbonyl) amino) -3-(4- (1- (4- (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3) -Il) Phenyl) Manufacture of methyl acrylate

4- (1- (4- (Trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) benzaldehyde (0.5 gram (g), 1.500 mmol (mmol)), 2 -((Tert-Butyloxycarbonyl) amino) -2- (dimethoxyphosphoryl) methyl acetate (0.491 g, 1.650 mmol) and 1,8-diazabicyclo [5.4.0] undeceth-7-en (DBU; 0.237 milliliters (mL), 1.575 mmol) are stirred together in dichloromethane (3 mL) at room temperature for 16 hours. The crude reaction mixture is adsorbed directly on a silica gel precolumn and purified on a 12 g silica gel column using a 0-50% ethyl acetate gradient in hexanes. The title compound is isolated as an off-white solid (0.550 g, 73%).

Example 2: 2-((tert-butoxycarbonyl) amino) -3-(4- (1- (4- (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) ) Manufacture of methyl propanoate

(Z) -2-((tert-butoxycarbonyl) amino) -3-(4- (1- (4- (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) ) Methyl acrylate (620 mg, 1.229 mmol) is dissolved in ethanol-ethyl acetate (1: 1,50 mL) at room temperature in a Parr pressure bottle. Palladium carbon (5%, 50% water by dry basis; 52.3 mg, 0.012 mmol) is added. Exhaust the bottle, fill it with nitrogen (2x), then do the final exhaust and add hydrogen gas up to 37 pounds per square inch (psi). Shake the mixture at room temperature for 16 hours. The reaction mixture is filtered and the filtrate is concentrated. The residue is dried under high vacuum at 50 ° C. for 2 hours. The title compound is isolated as a white solid (0.617 g, 98%).

Example 3: 1-methoxy-1-oxo-3- (4- (1- (4- (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) propane-2 -Manufacturing of aminium chloride

2-((tert-Butyloxycarbonyl) amino) -3-(4- (1- (4- (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) methyl propanoate Dissolve (100 mg, 0.197 mmol) in dichloromethane (3 mL). Add 4M hydrogen chloride (0.494 mL, 1.976 mmol) in dioxane. The reaction mixture is stirred at room temperature for 3.5 hours. The solvent is evaporated under a stream of nitrogen to give the title compound as a white solid (0.087 g, 100%).

Example 4: 2-((tert-butoxycarbonyl) amino) -3-(4- (1- (4- (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) ) Manufacture of propanoic acid

2-((tert-Butyloxycarbonyl) amino) -3-(4- (1- (4- (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) methyl propanoate (110 mg, 0.217 mmol) is stirred at room temperature in methanol (2 mL) and water (1 mL) to form a slurry. Lithium hydroxide hydrate (10.02 mg, 0.239 mmol) is added and the reaction is stirred at room temperature for 2 hours. Continue stirring for 2 hours while warming to 45 ° C. Tetrahydrofuran (3 mL) is added and stirring is continued at room temperature for 16 hours. The reaction mixture is diluted with water and ethyl acetate. The aqueous layer is acidified with a 1N aqueous hydrochloric acid solution. Separate layers. The organic layer is dried, filtered and concentrated. The title compound is isolated as a pale yellow solid (0.080 g, 75%).

Example 5: (Z) -2- (3- (3- (2-isopropyl-5-methylphenyl) -4-oxothiazolidine-2-iriden) ureido) -3- (4- (1- (4- (4- (4- (4-) Production of (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) methyl propanoate

1-Methoxy-1-oxo-3-(4- (1- (4- (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) propane-2 at 0 ° C. -Aminium chloride (87 mg, 0.196 mmol) is added in dichloromethane (10 mL) and water (5 mL) with sodium bicarbonate (165 mg, 1.965 mmol) and stirred for 15 minutes. Triphosgene (38.5 mg, 0.130 mmol) is added and the mixture is stirred for 45 minutes. The mixture is passed through a water retention cartridge and the organic phase is 2-imimino-3- (2-isopropyl-5-methylphenyl) thiazolidine-4-one (53.7 mg, 0.) in dichloromethane (5 mL). 216 mmol) and triethylamine (137 μL, 0.982 mmol) are added dropwise directly into the stirred solution. The reaction mixture is stirred at room temperature for 2 hours. The crude reaction mixture is adsorbed on silica gel. Purification by silica gel chromatography (12 g silica gel column) eluting with a 0-50% ethyl acetate gradient in hexanes gives the title compound as a yellow oil, which solidifies into solid foam when evaporated for extended periods of time (12 g silica gel column). 0.068 g, 51%).

Example 6: (Z)-(1- (3- (3- (2-isopropyl-5-methylphenyl) -4-oxothiazolidine-2-iriden) ureido) -2- (4- (1- (4) -Production of tert-butyl (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) ethyl) carbamic acid

2-((tert-Butoxycarbonyl) amino) -3-(4- (1- (4- (trifluoromethoxy) phenyl) -1H-1,2,4-triazole-3-yl) phenyl) propanoic acid ( 80 mg, 0.162 mmol) and 2-imino-3- (2-isopropyl-5-methylphenyl) thiazolidine-4-one (40.3 mg, 0.162 mmol) together in toluene (5 mL) at room temperature. Stir. Triethylamine (0.136 mL, 0.976 mmol) and diphenylphosphoryl azide (67.1 mg, 0.244 mmol) are added in that order. After 1 hour, an additional 2-imimino-3- (2-isopropyl-5-methylphenyl) thiazolidine-4-one (40.3 mg, 0.162 mmol) was added and the reaction was warmed to 50 ° C. for 90 minutes. Then, the mixture is stirred at room temperature for 16 hours. The crude reaction mixture is adsorbed on silica gel. Purification by silica gel chromatography (4 g silica gel column) eluting with a 0-50% ethyl acetate gradient in hexanes gives the title compound as a pale yellow solid (0.060 g, 50%).

Using the methods disclosed herein, the molecules listed below are provided as examples (Table 1).

Using the methods disclosed herein, the molecules listed below are also provided as examples (Table 2).

Example A: Bioassay for beet armyworm (Spodoptera exigua) (“BAW”) and cabbage looper (Trichoplussia ni) (“CL”) bioassay effective beet armyworm reduces its population. Has few parasites, diseases or predators. BAW is widespread in many weeds, trees, grasses, beans and crops. In various places, it is of economic concern with respect to asparagus, cotton, corn, soybeans, tobacco, alfalfa, sugar beet, pepper, tomatoes, potatoes, onions, peas, sunflowers and citrus fruits, among other plants. The cabbage looper is a member of the noctuidae, a family of moths. It is found all over the world. It is cabbage, cauliflower, broccoli, Brussels sprouts, tomatoes, cucumbers, potatoes, kale, cubs, mustards, peppers, eggplants, watermelons, melons, pumpkins, melons, melons, green beans, collars, lettuce, spinach, celery, parsley, beets. , Attacks pea, alfalfa, soybeans and cotton. This species is very destructive to plants because of its greedy leaf consumption. However, in the case of cabbage, they not only feed on the wrapper leaves, but may also dig into the developing head. Larvae consume three times their body weight in plant materials daily. The feeding site is marked by a large deposit of sticky, moist fecal material.

After all, control of these pests is important because of the above factors. In addition, molecules that suppress these pests (BAW and CL), known as chewing pests, are useful in controlling other pests that chew on plants.

Certain molecules disclosed in this document were tested against BAW and CL using the methods described in the Examples below. In reporting the results, we used the "BAW and CL Evaluation Table" (see Table Section).

Bioassay for BAW A bioassay for BAW was performed using the 128-well food assay. Prefilled (in each of the 8 wells) with 1 mL of artificial food to which 50 μg / cm ² of the test compound (dissolved in 50 μL of 90:10 acetone-water mixture) was applied and then dried. 1-5 second instar BAW larvae were placed in each well (3 mL) of the food tray. The trays were covered with a clear adhesive cover and kept at 25 ° C., 14:10 light-dark for 5-7 days. Percentage mortality was recorded for larvae in each well; then activity in 8 wells was averaged. The results are shown in the table entitled "Table ABC: Biological Results" (see Table section).

Bioassay for cabbage looper (CL) A bioassay for CL was performed using the 128-well food tray assay. Prefilled (in each of the 8 wells) with 1 mL of artificial food to which 50 μg / cm ² of the test compound (dissolved in 50 μL of 90:10 acetone-water mixture) was applied and then dried. 1-5 second instar CL larvae were placed in each well (3 mL) of the food tray. The trays were covered with a clear adhesive cover and kept at 25 ° C., 14:10 light-dark for 5-7 days. Percentage mortality was recorded for larvae in each well; then activity in 8 wells was averaged. The results are shown in the table entitled "Table ABC: Biological Results" (see Table section).

Example B: Bioassay for Myzus persicae (“GPA”) (Myzus persicae) GPA is the most influential aphid pest of the peach tree, reducing growth and swelling leaves. And kill various tissues. It is a pathogenic carrier for carrying plant viruses such as potato virus Y and potato leaf roll virus to members of the Solanaceae family of solanaceous / potatoes, and to many other food crops with various mosaic viruses. It is also dangerous because it works as a living organism. GPA attacks other plants such as broccoli, burdock, cabbage, carrots, cauliflower, radish, eggplant, sardine, lettuce, macadamia, papaya, pepper, sweet potato, tomato, creson and zucchini. GPA also attacks many ornamental crops such as carnations, chrysanthemums, white kale (flowering white cabbage), poinsettia and roses. GPA developed resistance to many pest control agents. After all, control of this pest is important because of the above factors. In addition, molecules that suppress this pest (GPA), known as sucking pests, are useful in controlling other pests that suck on plants.

Certain molecules disclosed in this document were tested against GPA using the methods described in the Examples below. In reporting the results, we used the "GPA Evaluation Table" (see the section on the table).

Cabbage seedlings grown in 3-inch pots and having 2-3 small (3-5 cm) true leaves were used as the test substrate. The day before the chemical application, 20-50 GPAs (wingless adult and larval stages) were laid on the seedlings. Four pots with individual seedlings were used for each treatment. The test compound (2 mg) was dissolved in 2 mL of acetone / methanol (1: 1) solvent to form a 1000 ppm stock solution of the test compound. The stock solution was diluted 5-fold with 0.025% Tween 20 in water to give a solution in 200 ppm test compound. A handheld aspirator sprayer was used to spray the solution until it ran down on both sides of the cabbage leaves. The reference plant (solvent test) was sprayed with a diluent containing only 20% by volume acetone / methanol (1: 1) solvent. The treated plants were kept in a retention room at about 25 ° C. and ambient relative humidity (RH) for 3 days prior to scoring. Evaluation was performed by counting the number of surviving aphids per plant under a microscope. Percentage suppression measured by the use of Abbott's modified formula (WS Abbott, "A Method of Computing the Effects of an insecticide" J. Econ. Entomol. 18 (1925), pp. 265-267). did.

Modified% suppression = 100 * (XY) / X
During the ceremony
X = Number of viable aphids on the solvent test plant, and
Y = number of surviving aphids on the treated plant.

The results are shown in the table entitled "Table ABC: Biological Results" (see Table section).

Example C: Bioassay for Aedes aegypti "YFM" (Aedes aegypti) YFM prefers to feed on humans during the day and is most often found in or near human settlements. YFM is a pathogen-borne organism for transmitting several diseases. It is a mosquito that can spread dengue and yellow fever viruses. Yellow fever is the second most dangerous car-borne illness after malaria. Yellow fever is an acute viral hemorrhagic disease, and up to 50% of untreated severely affected people will die of yellow fever. Every year, 200,000 cases of yellow fever are estimated worldwide, causing 30,000 deaths. Dengue fever is an unpleasant viral illness; because of the intense pain it can cause, it is sometimes referred to as "dengue fever" or "Break-heart fever". Dengue kills about 20,000 people each year. After all, control of this pest is important because of the above factors. In addition, molecules that suppress this pest (YFM), known as sucking pests, are useful in controlling other pests that afflict humans and animals.

Certain molecules described in this document were tested against YFM using the methods described in the sections below. In reporting the results, the “YFM evaluation table” was used (see the section on the table).

A master plate (equivalent to a 4000 ppm solution) containing 400 μg of molecules dissolved in 100 μL of dimethyl sulfoxide (DMSO) is used. The master plate of the assembled molecule contains 15 μL per well. To this plate, add 135 μL of 90:10 water / acetone mixture to each well. A robot (Biomek® NXP Laboratory) to distribute 15 μL of automations from a master plate to an empty 96-well shallow plate (“daughter” plate). Automation Workstation) is programmed. Six reps (“daughter” plates) are made per master. Immediately after the "daughter" plate made, the YFM larvae spread.

The day before the plate should be processed, mosquito eggs are placed in Millipore water containing liver powder (4 g in 400 mL) to initiate hatching. After making "daughter" plates using a robot, they are infested with 220 μL of liver powder / mosquito larvae mixture (about 1 day old larvae). After infesting the plate with mosquito larvae, cover the plate with a non-evaporative lid to reduce desiccation. Keep the plate at room temperature for 3 days before scoring. After 3 days, observe each well and score based on mortality.

Agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, polymorphs, isotopes and radionuclides The molecules of formulas 1 and / or formula 2 are prepared to be agriculturally acceptable acid addition salts. May occur. As a non-restrictive example, amine functional groups are hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, benzoic acid, citric acid, malonic acid, salicylic acid, malic acid, fumaric acid, oxalic acid, succinic acid, tartrate acid, lactic acid. , Gluconic acid, ascorbic acid, maleic acid, asparagic acid, benzenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, hydroxymethanesulfonic acid and hydroxyethanesulfonic acid can form salts. As a further non-limiting example, acid functional groups can form salts containing those derived from alkalis or alkaline earth metals as well as those derived from ammonia and amines. Examples of preferred cations include sodium, potassium and magnesium.

Molecules of formula 1 and / or formula 2 may be prepared as salt derivatives. As a non-restrictive example, salt derivatives can be made by contacting the free base with a sufficient amount of the desired acid to give the salt. The free base may be regenerated by treating the salt with a suitable dilute base aqueous solution such as dilute sodium hydroxide, potassium carbonate, ammonia and sodium bicarbonate aqueous solution. Pest control agents such as, for example, 2,4-D are often made more water soluble by converting them to their dimethylamine salts.

Molecules of formula 1 and / or formula 2 may be prepared into a stable complex with the solvent, which remains intact after removal of the non-complexed solvent. These complexes are often referred to as "solvates". However, it is particularly desirable to form a stable hydrate with water as a solvent.

Molecules of formula 1 and / or formula 2 may be ester derivatives. These ester derivatives can then be applied in the same manner as the molecules disclosed herein.

Molecules of formula 1 and / or formula 2 may be made as various polymorphs of crystals. Polymorphism is important in the development of pesticides because different crystalline polymorphs or structures of the same molecule can have very different physical properties and biological performance.

Molecules of formula 1 and / or formula 2 may be made with various isotopes. Of particular importance are molecules that have ² H (also known as juterium) instead of ¹ H.

Molecules of formula 1 and / or formula 2 may be made using various radionuclides. Of particular importance are molecules with ¹⁴ C.

Stereoisomers The molecules of formula 1 and / or formula 2 may exist as one or more stereoisomers. Thus, certain molecules can be produced as a racemic mixture. It will be appreciated by those skilled in the art that one stereoisomer may be more active than the other stereoisomer. The individual character isomers may be obtained by known selective synthesis methods, by conventional synthetic methods using divided starting materials, or by conventional division methods. A molecule disclosed herein can exist as more than one isomer. Various isomers include geometric isomers, diastereomers and enantiomers. Thus, the molecules disclosed herein include geometric isomers, racemic mixtures, individual stereoisomers and optically active mixtures. It will be appreciated by those skilled in the art that one isomer may be more active than the other. The structures disclosed in the present disclosure are depicted in only one geometric form for clarity, but are intended to show all geometric forms of the molecule.

Combination In another embodiment, one of the molecules of formula 1 and / or formula 2 having the same, similar or different mode of action as the mode of action of the molecule of formula 1 and / or formula 2 (“MoA”), respectively. It may be used in combination with the above compounds (in a composite mixture, or as a simultaneous or sequential application). The mode of action includes, for example: acetylcholineresterase (AChE) inhibitor; GABAergic chlorine channel antagonist; sodium channel modulator; nicotinic acetylcholine (nAChR) agonist; nicotinic acetylcholine receptor (nAChR) allosteric activator; chlorine channel activity. Agents; Immature hormone analogs; Various (miscellaneous) non-specific (multi-site) inhibitors; Selective wing-feeding blockers; Tick growth inhibitors; Insect mesenteric microbial disruptors; Mitochondria ATP synthase inhibitor; oxidative phosphorylation deconjugation mediated by disruption of proton gradient; nicotinic acetylcholine receptor (nAChR) channel blocker; chitin biosynthesis inhibitor type 0; chitin biosynthesis inhibitor type 1 Dehulling disruptors, dipterans; ecdison receptor agonists; octopamine receptor agonists; mitochondrial complex III electron transfer inhibitors; mitochondrial complex I electron transfer inhibitors; voltage-dependent sodium channel blockers; acetyl CoA carboxylase inhibition Agents; mitochondrial complex IV electron transfer inhibitors; mitochondrial complex II electron transfer inhibitors; and lyanodin receptor modulators.

In another embodiment, the molecules of formula 1 and / or formula 2 are acaricidal, algae-killing, bird-killing, bacterial-killing, bactericidal / antifungal, herbicidal, insecticidal, mollusc-killing, nematode-killing. It may be used in combination with one or more molecules that are worm-killing, nematode-killing and / or virus-killing (such as in compositional mixtures or for simultaneous or sequential application).

In another embodiment, the molecules of formula 1 and / or formula 2 are used as feeding inhibitors, bird repellents, chemical fertility agents, herbicides antidotes, insect attractants, insect repellents, mammalian repellents, mating disruptors, plants. It may be used in combination with one or more molecules that are activators, plant growth regulators and / or synergists (such as in compositional mixtures or for simultaneous or sequential application).

In another embodiment, molecules of formula 1 and / or formula 2 may be used in combination with one or more of the following compounds (in a composition mixture, or for simultaneous or sequential application)-(3-ethoxypropyl). ) Mercury bromide, 1,2-dichloropropane, 1,3-dichloropropene, 1-methylcyclopropene, 1-naphthol, 2- (octylthio) ethanol, 2,3,5-tri-iodobenzoic acid, 2,3 , 6-TBA, 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium, 2,3,6-TBA-sodium, 2,4 5-T, 2,4,5-T-2-butoxypropyl, 2,4,5-T-2-ethylhexyl, 2,4,5-T-3-butoxypropyl, 2,4,5-TB, 2,4,5-T-butmethyl, 2,4,5-T-butothyl, 2,4,5-T-butyl, 2,4,5-T-isobutyl, 2,4,5-T-isooctyl, 2,4,5-T-isopropyl, 2,4,5-T-methyl, 2,4,5-T-pentyl, 2,4,5-T-sodium, 2,4,5-T-triethylammonium , 2,4,5-T-trolamine, 2,4-D, 2,4-D-2-butoxypropyl, 2,4-D-2-ethylhexyl, 2,4-D-3-butoxypropyl, 2, , 4-D-ammonium, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-potassium, 2,4- DB-sodium, 2,4-D-butothyl, 2,4-D-butyl, 2,4-D-diethylammonium, 2,4-D-dimethylammonium, 2,4-D-diolamin, 2,4- D-Dodecylammonium, 2,4-DEB, 2,4-DEP, 2,4-D-ethyl, 2,4-D-heptylammonium, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2, , 4-D-pentyl, 2,4-D-potassium, 2,4-D-propyl, 2,4-D-sodium, 2,4-D-tefuryl, 2,4-D-tetradecylammonium, 2, , 4-D-triethylammonium, 2,4-D-tris (2-hydroxypropyl) ammonium, 2,4-D-trolamine, 2iP, 2-methoxyethi Lumermer chloride, 2-phenylphenol, 3,4-DA, 3,4-DB, 3,4-DP, 4-aminopyridine, 4-CPA, 4-CPA-diolamin, 4-CPA-potassium, 4- CPA-sodium, 4-CPB, 4-CPP, 4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate, 8-phenylmercuryoxyquinoline, abamictin, absicic acid, ACC, acifluorfen, acequinocyl , Acetamiprid, acetion, acetochlor, acetophos, acetoprole, acibenzoral, acibenzoral S-methyl, acifluorfen Acifluorfen sodium, acronifen, acrep, acrinathrin, allethrin, acrylonitrile, acynonapyr, acipetax, acipetax copper, acipetax copper, acipetax. (Alachlor), alanycarb, albendazole, aldiccarb, aldimorph, aldoxycarb, aldollin, allethrin, allethrin, allethrin ), Allosamidin, alloxydim, alloxydim sodium, allyl alcohol, allyxycarb, allorac, alpha-cypermethrin, alpha-endosulfan (alpha-end) acifluorfen (alpha-end) , Ametridione, allethrin, amibuzin, amicarbazone, amicartiazo Amicarthzol, amidithion, amidoflumet, amidosulfuron, aminocarb, aminocyclopyracrol potassium, aminocyclopyracrolmethyl, aminocyclopyraclormethyl, aminocyclopyraclorb. aminopyrlide), aminopyralide potassium, aminopyralidetris (2-hydroxypropyl) ammonium, aminopyriphen, amiprophos-methyl, amiprophos, amisulblom, amiton ), Amiton oxalate, amitraz, amitrol, ammonium sulfamate, α-naphthalene ammonium acetate, amobam, ampropylfos, anabasine, anabasin sulfate, ann. Simidol, anilazine, anilophos, anisuron, anthraquinone, antu, aphorate, aramite, arsenic trioxide, asomate, asomate. ), Ashlum, Ashram Potassium, Ashram Sodium, Athidathion, Atraton, Atrazine, aureofungin, aureofungin, aviglycine, aviglycine, aviglycine, azinphos Azadiractin, azaphenidin, azamethiphos, azimsulfuron, azinphos-ethyl, azinphos-ethyl, aziphosmethyl, aziprotoline (aziprotoline) , Azotoate, a Zoxystrobin, bachmedesh, barban, barium hexafluorosilicate, ammonium polysulfide, barthrin, BCPC, beflubutamid, beflubutamid, benaluxyl, benalaxyl Zoline dimethylammonium, venazoline ethyl, benazoline potassium, bencarbazone, benzlothiaz, benziocarb, benflularin, benfuralin, benfuralben, benfuracrab, benfuracrab, benfuracrab) ), Benoxacor, benoxafos, benquinox, bensulfuron, benzylfuronmethyl, bensulide, bensultap, benzyltap, bentalon , Benchivalib, benzivalib isopropyl, benzazole, bentlanil, benzadox, benzadoxammonium, benzalconium chloride, benzamacryl, benzamaclyl Benzamorph, benzfendizone, benzipram, benzobicyclon, benzophenap, benzophenylap, benzofluor, benzofluor, benzofluor, benzofluor, benzofluor, benzofluor, benzofluor Ximate, benzoylprop, benzoylprop ethyl, benzpyrimoxan, benzthiazuron, benzyl benzoate, benzylladene, velveline erberine), velverinclolide, beta-cyfluthrin, beta-cypermethrin, betaxazin, bicyclopyrone, bifenthrin, bifenazetebi. , Bifjunzhi, bilanafos, sodium biranafos, binapacryl, bingqingxiao, bioallethrin, bioallethrin, bioetanomethrin Bioresmethrin), biphenyl, bisazir, bismerthiazol, bispyribac, bispyribac sodium, bistrifluron, bitertanol, bithirtanol, bithirtanol, bithinol S (blastidin-S), borax, Bordeaux mixture, boric acid, boscalid, brassinolde, brassinolide ethyl, brevicomin, brodifacom, brodefalate Brofranylide, brofluthrinate, bromacil, bromacil lithium, bromacil sodium, alpha-bromadiolone, bromadiolone, bromethrin, bromethrin, bromethrin, bromethrin Phos (bromfenvinphos), bromoacetamide, bromobonil, bromobutide, bromocyclen, bromo-DDT, bromophenoxym, bromophos Ethyl, bromoxynil, bromoxynil, bromoxynil, bromoxynil, bromoxynil, butyl, bromoxynil, octanoate, bromoxynil, bromoxynil, bromoxynil, bromoxynil.
Xinyl potassium, brompyrazon, bromconazole, bronopol, bucarcollate, bufencarb, bufencarb, buminaphos, buminafose, buminafose, bupilimate, bupilimate Burgundy mixture, busulfan, butacarb, butachlor, butafenacil, butamiphos, butatiofos, butatiofos, butathiophos, butathiophos (Buthiobate), butiuron, butocarboxim, butonate, butopyronoxyl, butoxycarboxim, butocarboxim (butoxycarboxim), butocarboxim (butocarboxim), butocarboxim (butocarboxim) Butocarboxim, cacodylic acid, cadusafos, cafenstrol, calcium arsenate, calcium chlorate, calcium cyanamide, calcium polysulfide, carbinphos, cambendichol, camfochlor, camphorch. , Captafol, captan, carbamorph, carbanolate, carbaryl, carbasmulam, carbendadim, carbendazim, carbendazim, carbendazim, carbendazim ), Carbofuran, carbon disulfide, carbon tetrachloride, carbophenothion, carbosulfan, carboxazole, cal Carboxide, carboxin, carfentrazone, carfentrazone ethyl, carpropamide, cartap, cartap hydrochloride, carvacrol, carcarbone , Cellocidin, CEPC, ceralure, Cheshunt mixture, chinomethionat, chytosan, clobenthiazone, clobenhiazone, chromothene, chromothene. Chlordane, chlorammonium, chloramben-diolamine, chlorambenmethyl, chlorambenmethylammonium, chloramben sodium, chloramine phosphorus, chloramphenicol ), Chloraniforman, Chloranil, Chloranocryl, Chlorantraniliprole, Chlorazifop, Chlorazifop, Chlordane, Chlordane, Chlordane, Chlordane, Chlordane, Chlordane, Chlordane, Chlordane, Chlordane, Chlordane, Chlordane Chlorbenzuron, chlorbicclen, chlorbromuron, chlorbufam, chlordane, chlordane, chlordecon (chlordecone), chlordecon (chlordecone), chlordecon (chlordecone) (Chlorempenthrin), chlorethoxyphos, chloreturon, chlorfenac, chlorphenac ammonium, chlorphenac sodium, chlorfenapyr, chlorphenazole (chl) orphenazole), chlorphenethol, chlorphenprop, chlorphenson, chlorphensulfide, chlorphenvinphos, chlorfluenzal chlorfluaz. (Chlorflurazole), chlorfluren, chlorflulenmethyl, chlorflurenol, chlorflurenolmethyl, chloridazon, chlorimuron, chlorpyrifosethyl, chlormephos (chlormephos) , Chlormecourt chloride, chlornidine, chlornitrofen, chlornitrofenzilate, chlorodinitronaphthalene, chloroform, chloromebuform, chloromebuform, chloromethiuro, chloromethylon , Chlorophacinone sodium, chloropicrin, chloropon, chloroprallythrin, chloropropyllate, chlorothalonil, chlorotollon, chloroxuron, chloroxuron, chloroxuron. , Chlorphonium, chlorphonium chloride, chlorphoxim, chlorpyrifos, chlorprocarb, chlorpropham, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos. Chlorsulfuron, chlorthal, chlortaldimethyl, chlortalmonomethyl, chlor Thiamide (chlorthiamid), chlorthiophos, chromolinenate, cholinechloride, chromafenozide, cinerin I (cinerin I), cinerin II, cinerin, cinelin cinthin ), Ciobutide, cisanilide, cismethrin, clacyfos, cletodim, climbazole, climbazole, climbazole, cliocalcinac ), Clofencet, Clofenset potassium, Clofenthezine, Clofibric acid, Clohop, Clohopisobutyl, chromazone, clomeprop, cloprop, Coppergydim, copperlide, clopyralidmethyl, clopyralid-olamine, clopyralid potassium, clopyralidtris (2-hydroxypropyl) ammonium, cloquintoset, cloquintocet. cloquintocet-mexyl), chloranthlum, chloranthlum methyl, closantel, clothianidin, clotrimazole, clolixhonac, cloxyphonac, cloxyphonac, cloxyphonac , Copperonate, copper acetate, copper acetohydrate, copper arsenate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper silicate, copper sulfate, chromium acid Copper zinc, coumaclor, coumapuryl, coumapos, coumat Nitrile, coumitote, coumoxystrobin, CPMC, CPMF, CPPC, credazine, cresol, crimidine, crotamiton, crotamichoc (Cryolite), que-lure, cufraneb, cumyllon, cuprobam, cuprobum oxide, curcumenol, cyanamide, cyanatrin, cyanatrin, cyanatrin. Cyanophos, cyanophos, cyanophoate, cyanthraniliprole, cyazofamid, cyhalothrin, cyhalothrin, cyhalothrin, cyhalothrin, cyhalothrin, cyhalothrin, cyhalothrin, cyhalothrin. Cyclaniliprole, cyclothrin, cyclolate, cycloheximide, cycloplaterate, cycloprothrin, cyclopylothrin, cyclopyroxy, cyclopyrone, cyclopyranyl ), Cycloxydim, cyclulon, cyenopyraphen, cyflufenamide, cyflumethofen, cyfluthrin, cyhalothrin, cyhalothrin, cyhalothrin ), Cyhexatin, cymidazole, simazole hydrochloride, cymoxanil, cyometrilinil, cypendazol, cyperme Cypermethrin, cyperquat, cypercoat chloride, cyphenothrin, cyprazine, cyprazole, cyprococo
sodium, cyprodinil, cyprofuram, cypromid, cyprosulfamide, cyromazine, cylomazine, diazinon, diazinon, diazinon, diazinon, diazinon Dalapon-magnesium, Dalapon-sodium, daminozide, dayoutong, dazomet, sodium dazomet, DBCP, d-camphor, DCIP, DCPTA, DDT, decacarb. (Decafentin), decarbofuran, dehydroacetic acid, delachor, deltamethrin, demephion, demephion-O, demefion-S, demeton-dimethon-dimethon-dimethon -O-Methyl, Dimeton-S, Dimeton-S-Methyl, Dimeton-S-Methyl Sulfone, Desmedipham, desmethrin, d-fansilquebingjuzhi, Diazinon (Diafenthiuron), dialifos, di-allate, diamidafos, diatomaceous soil, diazinon, dibutyl phthalate, dibutyl succinate, dicamba didimethylba, dicamba dimethylba. , Dicambadiolamin, dicambaisopropylammonium, dicambamethyl, dicambaolamine, dicambapotassium, dicambasodium, dicambatrolamin, dicapton, dichlobenil, dichlobentiazox, dichlobentiazion, dichlobentiazion Fluandid, dichlone, dichloralrea, dichlorbenzuron, dichlov Dichlorvolurenol, dichlorflurenolmethyl, dichlormate, dichlormid, dichlorloven, dichlorprop, dichlorprop 2-ethylhexyl, dichlorvos. , Dichlorprop dimethylammonium, dichlorprop ethylammonium, dichlorprop isooctyl, dichlorpropmethyl, dichlorprop P, dichlorprop P2-ethylhexyl, dichlorprop P dimethylammonium, dichlorprop potassium, dichlor Prop P Potassium, Dichlorprop P Sodium, Dichlorprop Sodium, Dichlorvos, Dichlorvos, Dichlozoline, Diclobutrazol, Diclocymet, Dichlorvos, Dichlorvos, Dichlorvos, Dichlorvos, Dichlorvos, Dichlorvos, Dichlorvos, Dichlorvos ), Dichromedin sodium, dichloran, dichloromezotiaz, dichlorvoslam, dicofol, dicomulal, dichloryl, dichlorvosyl, dichlorvosyl, dichlorvos Dichloromethane, dieldrin, dienochlor, diethamquat, dietaccourt dichlorvos, dietatyl, dietatyl, dietatylethyl, dietofencarbide (dietofencarbo) (Difenacom), diphenoconazole, diphenopenten, diphenopentenethyl, diphenoxuron, difenzoquot, difenzocoat, diphenzocoat methylsulfate (difenzocoat) alone), diflovidazin, diflubenzuron, diflufenican, diflufenzopyr, diflufenzopyr sodium, diflumethyl sodium, diflumetrim , Dimethif, dimefluthrin, dimefox, dimefuron, dimepiperate, dimethachlone, dimethachlone, dimethoate, dimethoate, dimethoate , Dimethenamide, dimethenamide P, dimethipin, dimethirimol, dimethoate, dimethomorph, dimethomorph, dimethylphoslate, dimethyl, dimethyl, dimethyl dimethylvinphos, dimethilan, dimexano, dimidazon, dimoxystrobin, dinex, dinexzinezinezinezinezinezinezinezine (dinex-dinezine) , Diniconazole M, dinitramine, dinobuton, dinocup, dinocup-4, dinocup-6, dinocton, dinophenate, dinopenton, dinopenton, dinopenton, dinopenton ), Dinoseb, dimethoate acetate, dinosebammonium, dinosebdiolamin, dinoseb sodium, dinosebtrolamin, dinosulfon, dinotefuran, dinotefuran. , Dinoterbuacetate, dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion, dioxathion, diphacinone, diphacinone, diphacinone , Diphenylamine, dipropalin, dipropetrin, dipymethitrone, dipyrythione, diquat, diquat dibromid, disulfoton disulfoton disulfoton disulfoton disulfoton dispiron ), Disulfos, ditalimphos, dithianon, dithiclofos, dithioether, dithiopyr, diuron, d-limonene, DMPA, DNO. DNOC potassium, DNOC sodium, dodemorph, dodemorph acetate, dodemorph benzoate, dodicin, dodicin hydrochloride, dodicin sodium, dodine, dofenapyn, dominicalu Doramectin, drazoxolon, DSMA, dufluin, EBEP, EBP, ecdysterone, edifenphos, edifenphos, edifenphos, edifenphos, egrinazine, aroma methine , EMPC, empenthrin, endosulfan, endtal, endtal diammonene salt, endtal dipotassium salt, endtal disodium salt, endrin, endrin, enestrobulin (Endroburin), enoxastrobin (enoxastrob) in), EPN, epocholeone, epophenonan, epoxyconazole, eprinomethylin, epronaz, epronaz, epronazole, epsilonmethylthrone ), EPTC, erbon, ergocalciferol, erlujixiancaoan, esdeupalleutrine, esfenvalerate, esphenvalerate, esprocarb (Etaconazole), etaphos, etem, ethaboxam, ethachlor, ethalfluralin, ethamethulfuron, ethametsulfuron, ethametsulfuron, ethametsulfuron. Ethylphon, ethidimuron, ethiophencarb, ethiolate, ethiolate, ethion, ethiozin, ethiprole, ethylethyl, ethylome, ethylome ), Ethhohexdiol, ethoprophos, ethoxyphen, ethoxyphenethyl, ethoxyxyquin, ethoxysulfuron, ethoxysulfuron, ethoxysulfuron, ethychlozate, ethychlozate, ethychlozate. DDD, ethylene, ethylene dibromid, ethylene dichloride, ethylene oxide, ethylicin, ethyl mercury 2,3-dihydroxypropyl mercaptide, ethyl mercury acetate, ethyl mercury bromide, ethyl mercury chloride, ethyl mercury phosphate, ethinophen (Etofenprox), etnipromid, etobizandid, etofenprox, etoxazole, etridiazole, etrim
Ethylphos, eugenol, EXD, famoxadone, famphur, fenamidone, fenaminosulf, fenaminosulf, phenaminestrobin, fenaminstrobi Fenalimol, fenasulam, fenazaflor, fenazaquin, fenbuconazole, fenbutatin oxide, fenbutatin fox, fenclolazole, fenclolazole fenchlorphos, fenchlorim, fenethacarb, fenfluthrin, fenfluram, fenhexamide, fentotropan, fentropan, phenitropan, fentothione Fenobucarb, fenoprop, phenoprop 3-butoxypropyl, phenoprop-butometyl, phenoprop butothyl, phenoprop butyl, phenoprop isooctyl, phenoprop methyl, phenoprop potassium. Fenothiocarb, fenoxacrim, fenoxanil, fenoxaprop, phenoxaprop ethyl, phenoxaprop P, phenoxaprop P ethyl, fenoxasulfone fenoxycarb, fenpiclonil, fenpicoxamide, fenpiritrin, fenpropatrin, fenpropidin, fenpropidin, fenpropimorph (fenpropimorph) npyrazamine, fenpyroximate, fenquinotrione, fenridazon, fenridazone potassium, fenridazonepropyl, fenson, fensulfotion, fensulphothion, fenthulphothion fenthiaprop, fenthiaprop ethyl, fenthion, fenthion ethyl, fenthin, fentin acetate, fentin chloride, fentin hydroxydo, fentrazamide, fentrifanil, fenuron. ), Fenulon TCA, fenvalerate, ferbam, ferrimzone, ferrous sulfate, fipronil, franprop, franpropisopropyl, franprop M, franpropmethyl, furan. Prop M isopropyl, Franprop M methyl, Frazasulfuron, flocumafen, flometokuin, flonicamide, florasulam, florpyruxifene, florpyraux. Fluoripicoxamide, fluacrypyrim, fluazindolizine, fluazihop, fluazihopbutyl, fluazihopmethyl, fluazihop P, fluazihop P butyl, fluazinum (fluaz) fluazuron, flubendiamide, flubenzimine, flucarbazone, sodium flucarbazone, flucetosulfuron, fluculoluron, fluchloron ucyluloxuron, flucytrinate, fludioxonil, fluenetyl, fluenselfone, flufenacet, flufenacet, flufenenolim, flufenerim, flufenerim, flufenerim Fluphenoxystrobin, flufenprox, flufenpyr, flufenpyrethyl, flufluore, fluhexaphon, fluhexaphon, fluindapyl, flumelylflume, ), Flumetralin, flumethsulum, flumezin, fulmicrolac, fulmicrolacpentyl, flumioxazine, fulmipropin, flumophilon, flumophilon, flumophilon. Fluoroidide, fluopylam, fluorbenside, fluoridamide, fluoroacetamide, fluorodiphen, fluoroglycofen, fluorofluorifloimide, fluoromylophilin, fluoromylophilin ), Fluoronitrofen, fluopimomide, fluothiuron, fluotrimazole, fluoxastrobin, fluoxastrobin, fluoxastrobin, fluupoflo) Panate, flupropanate sodium, fluoridifurone, flupyrimi n), flupyrsulfuron, flupyrsulfuron methyl, flupyrusulfon methyl sodium, fluquinconazole, flurazole, flurenol, flurenolbutyl, flurenolmethyl, fluridone. , Flurochloridone, fluroxypyr, fluroxypyrbutmethyl, fluroxypyr-meptyl, flurprimidol, flursulfamide, flulusulfamide, flulusulfamide, flulusulfamide ), Flusulfamide, fluthiaset, fluthiaset methyl, flutianil, flutranil, flutriafol, fluvalinate, fluxamethamide (fluxamide) fluxyroxad, fluxofenim, holpet, homesaphen, homesaphen sodium, phonofos, foramsulfuron, forrumfuronate, formolformor Formethanate Hydrochloride, Formothion, Formparanat, Formparanate Hydrochloride, Fosamine, Hosamineammonium, Josetyl, Josetyl Aluminum, Fosmethylan, Hosmethylan , Fostiazate, fostietan, frontalin, fuberidazole, fukaojining, fukaomi, funaihecauring , Furalane, furalaxyl, furamethrin, furametpyr, furathiocarb, furcarbanil, flucarbanil, flucarbanil, fluconazole, furconazole ), Fulmecyclox, furophanate, furyloxyphen, gamma-cyhalothrin, gamma HCH, genit, diberelephosphate, gibberlin ), Glufosinate, Glufosinate Ammonium, Glufosinate P, Glufosinate P Ammonium Salt, Glufosinate P Sodium Salt, Glyodin, Glyoxime, Glyphosate, Glyphosate, Glyphosate Diammonium Salt, Glufosinate Ammonium salt, glyphosate ammonium salt, glyphosate potassium salt, glyphosate sesquisodium salt, glyphosate-trimethium salt, glyphosine, gossypurre, gossypurre, glufosinate, glufosinate, glufosinate, glufosinate , Glufosinate, halacrinate, halauxifen, harauxifenmethyl, halfenprox, halophenozide, halosafen, halosulfuron Haloxydine, Haloxyhop, Haloxyhop-etothyl, Haloxyhopmethyl, Haloxyhop P, HaloxyhopP Etotyl, Haloxyhop P Methyl, Haloxyhop Sodium, HCH, Hemel, Hem. Hempa, HEOD, heptachlor, heptafluthrin, heptenophos, heptopargil, herbimycin, hete
Heterophos, hexachloroacetone, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron, hexaflurate, hexafluure, hexamulle, hexamidh. Hexazinone, hexylthiophos, hexithiazox, HHDN, holosulf, huancaiwo, huancaiwo, huangkaoling, huangcaoling Lugaphen (hydrargaphen), slaked lime, hydrogen cyanide, hydroprene, hymexazol, hyquincarb, IAA, IBA, icaridin, imazaryl, imazaryl, imazaryl, imazaryl, imazaryl , Imazametabensmethyl, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapill isopropylammonium, imazaquin, imazakinammonium Imazakin sodium, imazetapyr, imazetapyrammonium, imazosulfuron, imibenconazole, imiciaphos, imicyafos, iminoctadine iminoctadine iminoctadine iminoctadine iminoctadine Iminoctadine Trialvesylate, imiprothrin, inabenfide, indanofan, indaziflam, indoxacarb, inezin ), Impylfluxam, iodobonil, iodocarb, iodomethane, iodosulfuron, iodosulfuronmethyl, iodosulfronmethyl sodium, iofenphosulfuron Sodium, ioxynil, ioxynil octanoate, ioxynil lithium, ioxynil sodium, ipazine, ipconazole, ipfencarbazone, ipfentrifluconazole, ipfentrium Ipflufenoquin, iprobenphos, iprodione, iprovalicarb, iprymidam, ipsdio, ipsodienol, ipsodienol, ipsodienol Isobenzan, isocarbamide, isocarbophos, ioxynil, isodrin, isofenphos, isofenphosmethyl, isofetamide, isofetamide, isofetamide. isolan), isomethiozin, isonoruron, isoporinate, isoprocarb, isoproporin, isoprothiolane, isoprothiolane, isoprothurane, isoprothurone, isoprothurone. (Isothioate), isotianil, isouron, isovaledione, isoxaben, isoxachlortole, isoxadifen, isofen. Sadiphenethyl, isoxaflutole, isoxapyribop, isoxathion, ivermectin, izopamfos, japonilus, japonilure, japonilure, japonilure, japonilure ), Jasmorin II, Jasmonic acid, Jiahuangchongzong, Jiajizengxiaolin, Jiaxiangjunzhi, Jiekaowan ), Juvenile Hormone I, Juvenile Hormone II, Juvenile Hormone III, Kadethrin, kappa-bifenthrin, kappa-tefluthrin, kasugamycin, kaletazin Zanpotassium, kasugamycin, kasugamycin hydrochloride, kejunlin, kelevan, ketospiradox, ketospiradox potassium, kinetin, kinoprene, kinoprene (Kusugamycin), lactophen, lambdasihalothrin, lancotrione, latilure, lead arsenate, lenacil, lepifectin, leptophos, lindene, lind. (Lineatin), linuron, lilimfos, littlere, loople, lfenuron, lvdingjunzi, lvxiankaolin, lvxiancaolin, lvxiancaolin, lvxiancaolin , Malathion, hydrazide maleate, malo Noben, maltodextrin, MAMA, mancopper, mancozeb, mandestrobin, mandipropamide, mandipropamid, manneb (manneb) ), MCPA, MCPA2-ethylhexyl, MCPA butothyl, MCPA butyl, MCPA dimethylammonium, MCPA diolamine, MCPA ethyl, MCPA isobutyl, MCPA isooctyl, MCPA isopropyl, MCPA methyl, MCPA olamine, MCPA potassium, MCPA sodium, MCPA thioethyl, MCPA trolamine. , MCPB, MCPB ethyl, MCPB methyl, MCPB sodium, mebenil, mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop 2-ethylhexyl, mecoprop ammonium Lamine, mecoprop-ethadyl, mecoprop-ethadyl, mecoprop isooctyl, mecoprop methyl, mecoprop P, mecoprop P-2-ethylhexyl, mecoprop P dimethylammonium, mecoprop P isobutyl, mecoprop potassium, mecoprop P potassium, mecoprop Sodium, mecoproptrolamin, medimeform, medinotherb, medinotherb acetate, medulre, mefenacet, mefenpyr, mefenpil diethyl, mefentrifluconazole (mefentrifluconazole) Mefluidide, mefluidodiolamine, mefluidide potassium, megatomic acid, menazon, mepanipyrim, meperfluthrin, meperfluthrin, mephenate (mephenate) mepiquat), mepicort chloride, mepicort pentabolate, mepronil ), Meptyldinocap, mercuric chloride, mercury oxide, mercuric chloride, merphos, mesoprazine, mesosulfuron, mesosulfuronmethyl, mesotrione, mesulphene. ), Mesulfenfos, metcamifen, metaflumizone, methalaxyl, methalaxyl M, metaldehyde, methamyl, methamyl, methamyl, methamyl, methamyl, methamifen, methamifen Bam potassium, carbam sodium, metazachlor, metazosulfuron, metazoxolon, metconazole, metepa, metepa, meteflazonz ), Metalpropalin, methamidophos, methasulfocarb, methazole, methophiloxam, methylomethion, methidathion, methiobation, methiobencalb. Ruflon (methiopyrisulfuron), methiotepa (methiotepa), methiozolin (methiozolin), methiuron (methiuron), methocrotophos (methocrotophos), methoprene (methomethone), methoprene (methomethone), methoprene (methomethone) ), Methothrin, methoxychlor, methoxyphenozide, methoxyphenone, methylaphorate (methy). l aphorate), methyl bromide, methyl eugenol, methyl iodide, methyl isothiocyanate, methylacetophos, methylchloroform, methyldymron, methylene chloride, methylmercury ben
Ester, Methylmercuric dicyandiamide, Methylmercuric pentachlorophenoxide, Methylneodecanamide, Metiram, Metobenzuron, Metbromuron, Metoflutrmelon ), Metominostrobin, Metoslum, Metoxadiazone, Metoxuron, Metraphenone, Metribuzin, metribuzin, metorufuron, methsulfon Methyltetraprole, mevinphos, mexacarbate, mieshan, milbemectin, milbemycin oxime, milbemycin oxime, milbemycin oxime, milbemycin oxime, milbemycin oxime, milbemycin oxime , Moguchun, molinate, molosultap, momfluorothrin, monalide, monisouron, monochloroacetic acid, monochromonuron ), Monosulfone ester, monuron, monun TCA, morphamquat, morphamcoat dichloride, moroxydine, moroxydin hydrochloride, morphectin, morzectin, morzid. ), MSMA, muscalure, microbutanil, myclozolin, N- (ethylmercury) -p-toluenesulfonanilide, nabum, naphthalofos (n). aftalofos, nared, naphthalene, naphthalene acetoamide, naphthalic anhydrate, naphthoxyacetic acid, naproanilide, napropamide (napropanylide), napropamide (napropamamide), napropamide ), Nebulon, niclosamide, niclosamide oramine, nicosulfuron, nicotine, nifluridide, nipyraclofen, nipyraclofen, nitempiram Nitrapylin, nitrilacarb, nitrofen, nitrofluorfen, nitrostyrene, nitrotal isopropyl, norbormide, norflurazon, nornicotine, nornicotine, nornicotine. (Novaluron), noviflumuron, nuarimol, OCH, octachlorodipropyl ether, octylinone, offrace, omethoate, olbencarb, orbencarb Chlorobenzene, orthosulfamuron, oryctalure, orysastrobin, oryzalin, ostol, ostramone, oxabetrinyl, oxabetrinyl, oxabetrinyl Oxadixyl, oxamate, oxamyl, oxapyrazon, oxapyrazon-dimoramine, oxapyrazon natamycin Mu, oxasulfuron, oxathiapiprolin, oxadichromefone, oxazosulfyl, oxine-copper, oxine-copper, oxolinic acid, oxopona Kispoconazole fumarate, oxycarboxin, oxydemethon-methyl, oxydeprofos, oxydisulfoton, oxyfluorfen, oxyfluorphen, oxyfluorphen Oxytetracycline, oxytetracycline hydrochloride, paclobutrazol, paichongding, para-dichlorobenzene, paraflulon, paraquat, paraquat, paraquat, parathion, paraquat ), Parathion Methyl, parinol, pebulate, pefurazoate, pelargonic acid, penconazole, pencycuron, pendimethalin, penfluphen, penfluphen, penflufen. Penoxslum, pentachlorophenol, pentachlorophenyllaurate, pentanochlor, penthiopyrad, pentomethrin, pentoxazone, perfluidone, perfluidone , Phenamacril, phenazine oxide, phenisopham, phencapton, phenmedifam, phenmedifamethyl, phenobenzlone nobenzuron, phenothrin, phenproxide, phenthoate, phenylmercurirea, phenylmercury acetate, phenylmercury chloride, phenylmercury derivative of pyrocatechol, phenylmercury nitrate, phenylmercury salicylate. , Phorate, phosacetim, phosalone, phosdiphen, phospholan, phospholanmethyl, phosglycin, phosmet, phosnitro, phosn Phosphin, phosphocarb, phosphorus, phostin, phoxim, phoximmethyl, phthalide, picarbutrazox, picloram, picloram, picloram, 2-ethylhexyl, picrolam Piclorum Methyl, Picrolam Oramine, Picrolum Potassium, Picrolam Triethylammonium, Picrolam Tris (2-hydroxypropyl) Ammonium, Picolinafen, Picoxystrobin, Pindone, Pindon Sodium, Pinoxaden (Pinoxaden), piperalin, piperalin, piperonyl butoxide, piperonyl cyclonene, piperophos, piproctanyl, piproctanyl, piproctanyl, piproctanyl, piproctanyl, piproctanyl, piproctanyl, piproctanyl, piproctanyl. ), Pyrimioxyphos, pirimiphos-ethyl, plymiphosmethyl, pliphenate, polycarbamate, polyoxynes, polyoxyphosphoris, polyoxylam, polyoxylam , Kariu Muazid, potassium cyanate, potassium diberephosphate, potassium naphthenate, potassium polysulfide, potassium thiocyanate, α-potassium sodium acetate, pp'-DDT, prallethrin, precosene I, precosene II, precosene III, Potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium, potassium. ), Prodiamine, prophenofos, profluazol, profluluralin, profluthrin, prophoxydim, propazine, progazine, propazine ), Prohexadione calcium salt, prohydrojasmon, promacyl, promecarb, prometon, promethrin, propazine, propazine (propazine), propazine (propazine) , Propazine dihydrochloride, propamocarb, propamocarb hydrochloride, propanil, propaphos, propaquizahop, propaquizahop, propargitin, propargite (Propetamphos), profam, propiconazole, propineb, propisochlor, propoxur, propoxycarbazone, propoxycarbazone, propoxycarbazone. Propyl isome, propyrisulfuron, propyzamide, proquinazid, prosuller, prosulfurin
falin), prosulfocarb, prosulfuron, prothidathion, prothiocarb, prothiocarb hydrochloride, prothioconazole, prothioconazole, prothiochoso Triphenbute, Proxan, Proxan sodium, prynachlor, pyrandon, pyreflumetofen, pyreblumide, pyrebroid, pyrethrincyl, pyrethrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin Pyraclovos, pyraclonil, pyraclostrobin, pyraflufen, pyraflufenethyl, pyrafluprole, pyramato, pyramethrin strobin pyramethrovin (Pyraoxystrobin), pyrapropone, pyrasulfotor, pyraziflumid, pyrazolynate, pyrazophos, pyrazophos, pyrazosulfuron , Pyrethrin, pyrethrin I, pyrethrin II, pyrethrins, pyribambenz-isopropyl, pyribambenz-isopropyl, pyribambenzpropyl, pyribencarbibri , Pyrethrin, pyridaben, pyridachromethyl, pyridafol, pyrridalyl, pyridary Dafenthion, pyrididate, pyridinitrile, pyrifenox, pyrifluquinazon, pyriftalid, pyriftalid, pyrimisulfan, pyrimisulfan Backmethyl, pyrimisulfan, pyrimisulfan, pyrimisulfan, pyrimite, pyrinuron, pyriophenone, pyriprole, pyripropol, pyripropanol, pyripropol Pyrisoxazole, pyrithiobac, pyrithiobac sodium, pyroran, pyroquilon, pyroxasulfone, pyroxysulfan, pyroxysulfan, pyroxysulfan, pyroxycyclol ), Quinacetol, quinacetol sulphate, quinalphos, quinalphosmethyl, quinazamid, quinclorac, quinconazolle, quinconazole, quinnoclamene Quinofumulin, quinonamid, quinothion, quinoxyfen, quintiophos, quintozone, quintozone, quintozene, quizalof, quizalofop, quizalofop, quizalofop, quizalofop. (Quwenzhi), queuingding, rabenzazole, rafoxande, rebemide, rescalure, Resmethrin, rhodethanil, rhodojaponin-III, rivavirin, rimsulfuron, rotenone, rotenone, lyana, lyana, ryana Simazine, salicylanilide, sanguinarine, santonin, schladan, sililiroside, sebutylazine, sebutylazine, sebuthylasene, sebuthylasene, sebuthylasem semiamitraz, semiamitratuchloride, sesamex, sesamolin, setoxydim, shungjia ancaolin, siduron, sylla sylla sylla sylla sylla sylla sylla sylla sylla ), Silica, sylthiofam, simazine, simeconazole, simetton, simetrin, sintofen, SMA, esmetholachlor (S-sodium) Sodium azide, sodium chlorate, sodium fluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodium orthophenylphenoxide, sodium pentachlorophenoxide, sodium polysulfide, sodium thiocyanate, sodium α-naphthalene acetate, sofamid ( sophamide, spinetram, spinosad, spirodiclophen, spiromethifen, spiropidion, spirotetramate, spirotetramin, spirotetramat Streptomycin, streptomycin sesquisulfate, strychnin, sulcatol, sulcofuron, sulcofuron sodium, sulcotrione, sulfurate, sulfurate, sulfurate, sulfurate. sulfiram, sulfluramid, sulfomethuron, sulfomethuronmethyl, sulfosulfuron, sulfotep, sulfoxafluoro, sulfoxide, sulfoxide, sulfoxide. T TCA etazil, TCA magnesium, TCA sodium, TDE, tebuconazole, tebufenozide, tebufenpyrado, tebufloquin, tebufloquin, tebupirimphos (tebuti) , Technazene, tecolam, teflubenzuron, tefluthrin, tefluthrine, tembotrione, tembotrione, temefos, temefos, temefos. ), Teralethrin, terbacil, terbucarb, terbuchlor, terbufos, terbumethon, terbutyrazin azine), terbutrin, tetcyclasis, tetrachloroethane, tetrachlorvinphos, tetraconazole, tetradiphon, tetrafluthrin, tetrafluthrone, tetrafluthrone, tetrafluthrone (Tetradiflutrin), tetramine, tetranactin, tetraniliprole, tetrasul, tallium sulfate, tenylchlor, thiamethoxam thiamethoxam, thiamethoxam All (thiadimluor), thiamethoxam (thiamethoxam), thiapronil (thiapronil), thiazafluron, thiazopyr, thiclophos, thiclophos, thiciophen Thiencarbazonemethyl, thifensulfuron, thifencelfuronmethyl, thifluzamide, thiobencarb, thiocarboxime, thiochlorfym Hydrochloride, thiocyclum oxalate, thiodiazole-copper, thiodicarb, thiofanox, thiofluoxymate, thiohempa, thiohempa, thiohempa thiomethon, thionazine, thiophanate, thiophanatemethyl, thioquinox, thiosemic arbaside), thiosultap, thiosultap diammonium, thiosultap disodium, thiosultap monosodium, thiotepa, thiram, thuringii
ensin), tiadinil, thiafenacil, thiaojiean, thiocarbazil, thiochlorim, tioxazaphen, tioxaziate, tioxytimid, tioxymidi , Tolfempyrad, tolprocarb, tolpyrate, tolylfluand, tolylmercury acetate, topramethrin, topramethrin, topramethrin, topramethrin tralomethrin, tralopylil, transfluthrin, transpermethrin, tretamine, triacontanol, triadimephon, triadimephon, triadimephon, triadimephon Tri-allate, triamiphos, triapenthenol, triarathene, triarimol, triasulfuron, triazylfuron, triazamate, triazithel. triaziflam, triazophos, triazoxide, tribenuron, trivenuronmethyl, tribufos, tributyltin oxide, trichlorthrin oxide, tricylmyl, tricylphone, tricambithrin ), Trichlormethaphos-3, trichloronat, triclopyr, trichloropyrbuti Le, triclopyrethyl, triclopyricarb, triclopyrtriethylammonium, tricyclazole, tridemorph, tridiphane, trietazine, triphenzine, trifenmorph Trifloxystrobin, trifloxysulfuron, trifluxylfuron sodium salt, trifludimoxazine, triflumezopyrim, triflumezophilum, triflumyl, triflumyl, triflumyl, triflum, triflum Trifluralin, triflusulfuron, triflusulfuron methyl, trihop, trihopmethyl, triphopsime, trifoliane, trihydroxytriazine, triptolidetrimerdre. Trimethuron, trinexapac, trinexapac ethyl, triprene, tripropindan, triptolide, tritac, triticonazole triptolide, trunc-call, tyclopyrazoflor, uniconazole, uniconazole P, urbacide, uredepa, uredepa, valeridepa, valerate val Validate, validamycin, vamidothion, vangard, vaniliprole, vernolate, vinclozolin, warfarin, warfarin Walfarin sodium, xiaochongliulin, xinjunan, xiwojunan, XMC, xylachlor, xylenols, xylylzing, xylyzylzylzylzylzylzyl (Zeatin), zengxiaoan, zetasipermetrin, zinc naphthenate, zinc phosphate, zinc thiazole, zineb, ziram, zolaprofos, zoxamide, zomif. Zuomihuanglong, α-chlorohydrin, α-ecdysone, α-multistriatin and α-naphthalene acetate. For more information http: // www. alanwood. net / pesticides / indexes. html. Check out "Compendium of Pesticide Common Names" in. See also "The Pesticide Manual" 15th Edition, edited by CDS Tomlin, copyrighted or earlier or more recent editions by the British Crop Production Council in 2009.

In another embodiment, the molecules of Formula 1 and / or Formula 2 may be used in combination with one or more biopesticides (such as in a composition mixture or for simultaneous or sequential application). The term "biopesticides" is used for microbial biological pest control controls that are applied in a manner similar to chemical pest control agents. These are usually bacterial, but there are also examples of fungal and fungal suppressants, including the genus Trichoderma spp. And Ampelomyces quisqualis (suppressant for powdery mildew). Bacillus subtilis is used for the control of plant pathogens. Weeds and rodents have also been suppressed using microbial agents. One well-known example of an insecticide is Bacillus thuringiensis, a bacterial disease of the order Lepidoptera, Coleoptera and Diptera. It appears to be more environmentally friendly than synthetic pest control agents as it has little effect on other organisms. Biological insecticides include: insect pathogenic fungi and molds (eg Metarhizium anisopriae); insect pathogenic nematodes (eg Steinernema).
Feltier); and products based on insect pathogenic viruses such as codling moth (Cydia pomonella) granulovirus.

Other examples of entomopathogenic organisms include, but are not limited to, bacroviruses, bacteria and other prokaryotes, fungi / molds, protozoa and microsporidia. Organism-derived pesticides include rotenone, veratridine and microbial toxins, insect-resistant or resistant plant species; and recombinant DNA to produce pesticides or convey insect resistance to genetically modified organisms. Includes, but is not limited to, organisms modified by law. In one embodiment, the molecules of formula 1 and / or formula 2 may be used with one or more biopesticides in the area of seed treatment and soil improvement. The Manual of
Biocontrol Agents provides an overview of available biological pesticide (and other biologically based inhibitory) products. Copping L. G. (Ed.) (2004). The Manual of Biocontrol Agents (formally Biopesticide Manual) 3rd Edition. British Crop Production Council (BCPC), Farnham, Surrey UK.

In another embodiment, the above possible combinations may be used in various weight ratios. For example, in a two-component mixture, the weight ratio of the molecules of Formula 1 and / or Formula 2 can be from about 100: 1 to about 1: 100; in another example, the weight ratio is about 50: 1. Can be from about 1:50; in another example, the weight ratio can be from about 20: 1 to about 1:20; in another example, the weight ratio can be from about 10: 1 to about 1: 20. Can be 10; in another example the weight ratio can be from about 5: 1 to 1: 5; in another example the weight ratio can be from about 3: 1 to about 1: 3. Yes; and in the last example, the weight ratio can be about 1: 1. However, a weight ratio of less than about 10: 1 to about 1:10 is preferred. It may also be preferred to use a 3 or 4 component mixture comprising one or more molecules of formula 1 and / or formula 2 and one or more other compounds from the possible combinations described above.

Preparations Pest control agents are rarely suitable for application in their pure form. Pest control agents can be used in the required concentrations and in suitable forms, usually with the addition of other substances, to allow for ease of application, handling, transportation, storage and maximum pest control activity. is necessary. Thus, pest control agents can be, for example, baits, concentrated emulsions, dusts, emulsifiable concentrates, fumigants, gels, granules, microcapsules, seed treatments. Seed treatments, suspension concentrations, suspo emulsions, tablets, water soluble liquids, water-dispersible granules or dry flowers, wettable powders and polar fluids. Prepare in trace solutions (ultra low volume solutions). For further information on the type of the preparation, see "Catalogue of Pesticide Formation Type and International Coding System" by ^CropLife International (2, 5th Edition).

Most often, pest control agents are applied as aqueous suspensions or emulsions prepared from concentrated preparations of such pest control agents. Such water-soluble, water-suspendable or emulsifiable preparations are solids commonly known as wettable powders or water-dispersible granules or liquids commonly known as emulsifiable concentrates or aqueous suspending agents. .. Wettable powders that may be compressed to form water-dispersible granules include a close mixture of pest control agents, carriers and surfactants. The concentration of the pest control agent is usually about 10% by weight to about 90% by weight. The carrier is usually selected from attapargit clay, montmorillonite clay, diatomaceous earth or purified silicate. Effective surfactants that make up about 0.5% to about 10% of wettable powders are nonionics such as sulfonated lignin, condensed naphthalene sulfonate, naphthalene sulfonate, alkylbenzene sulfonate, alkyl sulfate and ethylene oxide adducts of alkyl phenol. Found in sex surfactants.

The emulsifiable concentrate of the pest control agent is as simple as about 50-about 500 grams per liter of liquid dissolved in a carrier which is a mixture of a water-miscible solvent or a water-immiscible organic solvent and an emulsifier. Contains high concentrations of pest control agents. Useful organic solvents include aromatic compounds, especially xylene and petroleum distillates, especially high boiling point naphthalene and olefinic moieties of petroleum such as heavy aromatic naphtha. Terpenic solvents containing rosin derivatives, aliphatic ketones such as cyclohexanone and other organic solvents such as complex alcohols such as 2-ethoxyethanol may also be used. Suitable emulsifiers for emulsifiable concentrates are selected from conventional anionic and nonionic surfactants.

The aqueous suspending agent comprises a suspension of a water-insoluble pest control agent dispersed in an aqueous carrier at a concentration in the range of about 5% by weight to about 50% by weight. Suspensions are prepared by finely grinding the pest control agent and mixing it vigorously in a carrier containing water and a surfactant. Inorganic salts and components such as synthetic or natural rubber may be added to increase the density and viscosity of the aqueous carrier. It is often most effective to simultaneously grind and mix the pest control agent by preparing an aqueous mixture and homogenizing it in an instrument such as a sand mill, ball mill or piston homogenizer.

Pest control agents may also be applied as a granular composition, which is particularly useful for soil applications. The granular composition usually contains from about 0.5% to about 10% by weight of pest control agent dispersed in a carrier containing clay or a similar substance. Such compositions are usually obtained by dissolving the pest control agent in a suitable solvent and applying it to a pre-formed granular carrier with a suitable particle size in the range of about 0.5 to about 3 mm. Prepared. Such compositions may also be prepared by making doughs or pastes of carriers and compounds, crushing and drying to obtain the desired granular size.

The pest control agent containing the pest control agent is prepared by closely mixing the pest control agent in powder form with a suitable fine powdered agricultural carrier such as kaolin clay, crushed volcanic rock and the like. The fine powder can optionally contain from about 1% to about 10% pest control agent. They can be applied as a seed coat or as a foliar spray using a dust blower machine.

It is equally practical to apply pest control agents in the form of suitable organic solvents, solutions in petroleum such as spray oils commonly used in agricultural chemistry.

Pest control agents can also be applied in the form of aerosol compositions. In such compositions, the pest control agent is dissolved or dispersed in a carrier that is a pressure-generating propellant mixture. The aerosol composition is packed in a container from which the mixture is distributed via a spray valve.

Mixing the pest control agent with food and / or attractants forms a pest control agent bait. When pests eat food, they also consume pest control agents. The bait may take the form of granules, gels, fluid powders, liquids or solids. They can be used in pest habitats.

Fumigants are pest control agents that have a relatively high vapor pressure and can therefore exist as a gas at a concentration sufficient to kill pests in soil or confined spaces. The toxicity of fumigants is proportional to their concentration and exposure time. They are characterized by good diffusion for diffusion and act by penetrating the respiratory system of the pest or by being absorbed through the cuticle of the pest. Fumigants are applied under gas-impermeable sheets, in gas-sealed rooms or buildings, or in special indoor storage products for the control of pests.

Pest control agents can be microencapsulated by suspending pest control particles or droplets in various types of plastic polymers. Microcapsules of various dimensions, solubility, wall thickness and permeability can be formed by changing the chemistry of the polymer or by changing the factors in the treatment. These factors govern the rate at which the active ingredient in it is released, which in turn affects residual performance, rate of action and product odor.

An oil solution concentrate is prepared by dissolving the pest control agent in a solvent that will keep the pest control agent in solution. Pest control oils usually knock down pests faster than other preparations due to the dissolution of the pest control solvent itself and the waxy coating of the rind that improves the rate of absorption of the pest control. And kill. Other benefits of the oil include higher storage stability, better crevice penetration and better adhesion to greasy surfaces.

Another embodiment is an oil-in-water emulsion, where the emulsion contains oily droplets, each of which is given a layered liquid crystal coating and is dispersed in the aqueous phase, where each oily droplet is at least one species. Contains an agriculturally active compound of: (1) at least one nonionic lipophilic surfactant, (2) at least one nonionic hydrophilic surfactant and (3) at least one ion. Individually coated with a monolamellar or oligolamellar layer containing a sex surfactant, where the droplets have an average particle size of less than 800 nanometers. Further information regarding such embodiments is disclosed in US Patent Publication No. 2007/0027034A1 published February 1, 2007, with patent application No. 11 / 495,228. For ease of use, this embodiment is referred to as "OIWE".

For further information, D. Check out "Insect Pest Management" 2nd Edition, Copyright CAB International (2000) by Dent. In addition, for more detailed information, Arnold Mallis's "Handbook of Pest Control-The Behaver, Life History, and Control of Household Pests", 9th Edition, GEM. Please check the copyright in 2004.

Other Preparation Ingredients Such preparations may also contain other ingredients if the molecules generally disclosed in Formula 1 are used in the preparation. These ingredients include wetting agents, spreading agents, adhesives, penetrants, buffers, sequestrants, drift reducing agents, compatibilizers, defoamers, detergents and emulsifiers. Is not limited to these (this is a non-exhaustive and non-exclusive list). Some ingredients will be explained immediately.

Wetting agents, when added to a liquid, are substances that improve the spread or osmotic power of the liquid by reducing the interfacial tension between the liquid and the surface on which it is spread. Wetting agents have two main functions in pesticide preparations: to increase the rate of wetting of powders in water during processing and production to make concentrates for soluble or suspending concentrates; It is used to reduce the wetting time of the wettable powder while mixing the water with the product in the spray tank and to improve the penetration of water into the water-dispersible granules. Examples of wetting agents used in wettable powders, suspending concentrates and water-dispersible granule preparations are: sodium lauryl sulfate; sodium dioctyl sulfosuccinate; alkylphenol ethoxylates; and fatty alcohol ethoxylates.

A dispersant is a substance that adsorbs on the surface of a particle, helps maintain the state of dispersion of the particle, and prevents the reaggregation of the particle. Dispersants are added to the pesticide preparation to facilitate dispersion and suspension during production and to ensure particle redispersion in water in the spray tank. They are widely used in wettable powders, suspending concentrates and water-dispersible granules. Surfactants used as dispersants have the ability to strongly adsorb on the surface of the particles and provide a charge or steric barrier to the reaggregation of the particles. The most commonly used surfactants are anionic, nonionic or a mixture of the two types. The most common dispersant for wettable powder preparations is sodium lignosulfonate. For suspending concentrates, very good adsorption and stabilization can be obtained with polyelectrolytes such as sodium naphthalene sulfonate formaldehyde condensates. Tristyrylphenol ethoxylate phosphate esters are also used. Nonionic surfactants such as alkylarylethylene oxide condensates and EO-PO block copolymers may be combined with anionic surfactants as dispersants for suspension concentrates. In recent years, a new type of highly high molecular weight polymer surfactant has been developed as a dispersant. They have a very long hydrophobic "main chain" and a large number of ethylene oxide chains, forming the "teeth" of a "comb" type surfactant. These high molecular weight polymers can provide very good long-term stability to the suspension concentrate because the hydrophobic backbone has many fixation points on the particle surface. Examples of dispersants used in pesticide preparations are: sodium lignosulfonate; sodium sodium phthalene sulfonate formartehide condensate; tristyrylphenol ethoxylate phosphate ester; aliphatic alcohol ethoxylates; alkylethoxylate; EO-PO block Copolymers; and graft copolymers.

An emulsifier is a substance that stabilizes a suspension of a drop of one liquid phase in another liquid phase. In the absence of emulsifier, the two liquids separate into two immiscible liquid phases. The most commonly used emulsifier blends contain an oil-soluble calcium salt of an alkylphenol or fatty alcohol with 12 or more ethylene oxide units and dodecylbenzene sulfonic acid. Hydrophilic-lipophilic balance (“HLB”) values in the range 8-18 will usually give excellent stable emulsions. Emulsion stability may be improved by adding a small amount of EO-PO block copolymer surfactant.

The solubilizer is a surfactant that forms micelles in water at a concentration higher than the critical micelle concentration. The micelle can then dissolve or solubilize the water-insoluble material within the hydrophobic portion of the micelle. The types of surfactants commonly used for solubilization are nonionic surfactants, sorbitan monooleates, sorbitan monooleate ethoxylates and oleic acid methyl esters.

Surfactants can be used alone or in combination with other additives such as mineral oil or vegetable oil as an adjunct to the spray tank mixture to improve the biological performance of the pest control agent on the target. be. The type of surfactant used for bioenhancement generally depends on the nature and mode of action of the pest control agent. However, they are often nonionic surfactants such as: alkyl ethoxylates; linear aliphatic alcohol ethoxylates; aliphatic amine ethoxylates.

A carrier or diluent in an agricultural preparation is a material added to a pest control agent to provide a product of the required concentration. The carrier is usually a material with a high absorption capacity, while the diluent is usually a material with a low absorption capacity. Carriers and diluents are used in the preparation of fine powders, wettable powders, granules and water-dispersible granules.

Organic solvents are primarily used in the preparation of emulsifiable concentrates, oil-in-water emulsions, suspo emulsions and trace preparations as well as to a lesser extent granular preparations. A mixture of solvents may also be used. The first major group of solvents are aliphatic paraffin oils such as kerosene or purified paraffin. The second major group (and most common) comprises aromatic solvents such as xylene as well as higher molecular weight fractions of C9 and C10 aromatic solvents. Chlorinated hydrocarbons are useful as an auxiliary solvent to prevent the crystallization of pest control agents when emulsifying the preparation into water. Alcohol may be used as an auxiliary solvent to improve the dissolving power. Other solvents may include vegetable oils, seed oils and esters of vegetable oils and seed oils.

Thickeners or gelling agents are primarily used in the preparation of suspension concentrates, emulsions and suspo emulsions to alter the flow rheology and flow characteristics of liquids and to separate and precipitate dispersed particles or droplets. It is used to prevent the disease. Thickening, gelling and anti-sedimenting agents are generally included in two sectors: water-insoluble particles and water-soluble polymers. It is possible to prepare suspension concentrate preparations using clay and silica. Examples of these types of materials include, but are not limited to, montmorillonite, bentonite, magnesium aluminum silicate and attapulsite. For many years, water-soluble polysaccharides have been used as thickening-gelling agents. The most commonly used types of polysaccharides are natural extracts of seeds and seaweeds or synthetic derivatives of cellulose. Examples of these types of materials include, but are not limited to, guar gum; locust bean gum; carrageenan; alginate; methyl cellulose; sodium carboxymethyl cellulose (SCMC); hydroxyethyl cellulose (HEC). Other types of anti-sediment agents are based on modified starches, polyacrylates, polyvinyl alcohols and polyethylene oxides. Another excellent anti-sedimenting agent is xanthan gum.

Microorganisms can cause damage to the prepared product. Therefore, preservative agents are used to eliminate or reduce those effects. Examples of such agents are: propionic acid and its sodium salts; sorbic acid and its sodium or potassium salts; benzoic acid and its sodium salts; p-hydroxybenzoic acid sodium salts; p-hydroxybenzoate methyl; and 1, 2-Benzisothiazolin-3-one (BIT) is included, but is not limited to these.

The presence of surfactant often foams water-based preparations during preparation and mixing operations during application via a spray tank. Antifoaming agents are often added during the preparation phase or before filling the bottle to reduce the tendency to foam. There are generally two types of defoamers, namely silicone and non-silicone. Silicone is usually an aqueous emulsion of dimethylpolysiloxane, while non-silicone defoamers are water-insoluble oils or silica such as octanol and nonanol. In both cases, the function of the defoamer is to transfer the surfactant from the air-water interface.

"Green" agents (eg, auxiliaries, surfactants, solvents) can reduce the overall environmental footprint of crop protection preparations. Green agents are biodegradable and generally derive from natural and / or sustainable resources such as plant and animal resources. Specific examples are: vegetable oils, seed oils and esters thereof, as well as alkoxylated alkyl polyglucosides.

For further information, D. A. See copyright in 1998 by "Chemistry and Technology of Agrochemical Forums" edited by Knowles. A. S. Perry, I. Yamamoto, I. Ishayaya, and
R. See also copyright in 1998 by Springer-Verlag, "Insecticides in Agriculture and Environment-Retrospects and Projects" by Perry.

Pests Generally, pests of formula 1 and / or formula 2 are pests such as ants, aphids, beetles, blemishes, cockroaches, crickets, scissors, fleas, flies, butterflies, worms, termites, wading butterflies, mites. , Ga, nematodes, scales, cockroaches, termites, lizards, ticks, bees and fleas.

In another embodiment, the molecules of formula 1 and / or formula 2 may be used to control pests in the phylum C. elegans (Phyla Nematoda) and / or the phylum Arthropod (Phyla Arthropoda).

In another embodiment, the molecules of formula 1 and / or formula 2 are pests of the pests in the subphylum Chelicerata, the subphylum Subphyla Myriapoda and / or the subphylum Hexapoda. May be used for suppression.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to control pests in the arachnids (Arachnida), symphyla and / or insects (Insecta).

In another embodiment, the molecules of formula 1 and / or formula 2 may be used to control pests of the order Order Anopura. A non-exhaustive list of specific genera includes Haematopinus spp., Hoplopleura spp., Linognatus spp., Pediculus spp. And Polyplax spp. Is included, but not limited to these. A non-exhaustive list of certain species includes Haematopinus asini, Haematopinus suis, and Linognatus.
setosus, Linognatus ovils, Pediculus humanus capitis, Pediculus humanus pupitis, Pediculus humanus puss, pediculus humanus, pediculus, pediculus, pediculus, pediculus, pediculus, humanus

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests in the order Coleoptera. A non-exhaustive list of specific genera includes the genera Acanthoscellides spp., Agriotes spp., Anthonomus spp., Apion spp., Apogonia sp. ), Auracophora spp., Bruchus spp., Cerosterna spp., Cerotoma spp., Ceutorhinx spp. , Colaspis spp., Ctenicera spp., Curculio spp., Cyclocephala spp., Diablotica spp., Hypera spp.
spp. ), Ips spp., Lyctus spp., Megacelis spp., Meligethes spp., Otiorhinchus spp., Pantomorus spp. Phyllophaga spp., Phyllotretta spp., Rhizotrogus spp., Rynchites spp., Rynchites spp., Rynchossp. Includes, but is not limited to, the genus Sphenophorus spp., The genus Sitophilus spp. And the genus Tribolium spp. A non-exhaustive list of certain species includes Acanthoscelides obtectus, Agrilus planipennis, Anoplophora gravipennis, Anoplophora grablipennis, Anoplophora grablipennis, Anoplophora grablipennis. spretulus, Atmaria linearis, Boll weevil punctiventris, Bruchus pisolum, Carosobrus psilus
hemipterus), Kashida-Bittata (Cassida vittata), Serotoma-Tsurifurukata (Cerotoma trifurcata), Seutoruhinkusu-Ashimirisu (Ceutorhynchus assimilis), Seutoruhinkusu-Napi (Ceutorhynchus napi), Konoderusu-Sukararisu (Conoderus scalaris), Konoderusu-Suchigumosusu (Conoderus stigmosus) , Conoderus nenufar, Conoderus nichida, Criocelis asparagus, Cryptrestes ferrugineus (Cryptolestes turcicus), shea Lind good Putsu Luz Adosuperususu (Cylindrocpturus adspersus), Deporausu-Maruginatsusu (Deporaus marginatus), Derumesutesu-Rarudariusu (Dermestes lardarius), Derumesutesu-Makuratsusu (Dermestes maculatus), Epilachna-Baribesuchisu (Epilachna varivestis), Fausuchinusu - Kubae (Faustinus cubae), Hirobiusu Palace (Hylobius pales), Hipera-Posuchika (Hypera postica), Hipotenemusu-Hamupei (Hypothenemus hampei), Rashioderuma-Serikorune (Lasioderma serricorne), Leptinotarsa Desemurineata (Leptinotarsa decemlineata), Riogenisu-Fusukusu ( Liogenys fuscus, Liogenys sutralis, Lishorhoptrus oryzophilus, Maecolaspis jolibetis, Maecolaspis jolibeti, Mela
communis), Meligethes aeneus, Melolonta melolontha, Oberea brevis, Obelia linearis, Oberea linearis, Oryzaephilus mercator), Oryza Efiru vinegar Surinamenshisu (Oryzaephilus surinamensis), Ourema-Meranopusu (Oulema melanopus), Ourema oryzae (Oulema oryzae), Firofaga-Kuyabana (Phyllophaga cuyabana), Popiria-japonica (Popillia japonica), professional Sutefanusu-Tsurunkatsusu ( Prostephanus trancatus, Rhizopertha dominica, Sitona lineatus, Sitophilus granarius, Sitophilus oryzae
oryzae, Sitophilus zeamais, Stegobium paniceum, Tribium castaneum, Tribium confusedulum (Tribolium)
coder variables) and Zabrus tenebrioides are included, but not limited to these.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the order Earwig (Order Dermaptera).

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the order Cockroach (Order Blattaria). A non-exhaustive list of certain species includes Blattella germanica, Blatta orientalis, Parcoblatta pennsylvanica, Periplaneta pennsylvanica, Periplaneta araneta era. D (Periplaneta australasiae), Periplaneta brunnea, Periplaneta fuliginosa, Pycnosalus sulinapunisa, Pycnosalus, Pycnosalus, Pycnosalus.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to control pests of the Order Diptera. A non-exhaustive list of specific genera includes Aedes spp., Agromyza spp., Anastrepha spp., Anofeles spp., Batrocera spp. , Ceratis spp., Chrysops spp., Cochliomyia spp., Contalinia spp., Culex spp., Dacineura sp.
spp. ), Delia spp., Drosophila spp., Fannia spp., Hylemya spp., Liriomyza spp., Musca spp. Includes, but is not limited to, the genus Phorbia spp., The genus Tabanus spp. And the genus Tipula spp. A non-exhaustive list of certain species is Agromyza
frontella), Anasutsurefa-Susupensa (Anastrepha suspensa), Anasutsurefa-Rudensu (Anastrepha ludens), Anasutsurefa-Oburiga (Anastrepha obliga), Bakutsurosera-Kukurubitae (Bactrocera cucurbitae), Bakutsurosera-Dorusarisu (Bactrocera dorsalis), Bakutsurosera-Inbadensu (Bactricera invadens) , Bactrocera zonata, Ceratisis capitata, Dasineura bracicae, Delia platara (Delia platara), Faria plata, Faria gas terrorism Filth-tae steel Naris (Gasterophilus intestinalis), Gurashiria-Peruseae (Gracillia perseae), Haematobia-Iritansu (Haematobia irritans), Hipoderuma-Rineatsumu (Hypoderma lineatum), Ririomiza-Burashikae (Liriomyza brassicae), Merofagusu-Obinusu (Melophagus ovinus) , Musca autumnalis, Musca domestica, Oestrus ovis, Oscinella frit, Pegomira betae (Pe)
gomya betae), Pushira-Rosae (Psila rosae), Ragorechisu-Serashi (Rhagoletis cerasi), Ragorechisu pomonella (Rhagoletis pomonella), Ragorechisu-Mendakusu (Rhagoletis mendax), Shitojipuroshisu-Moserana (Sitodiplosis mosellana) and Sutomokushisu-Karushitsuransu (Stomoxys calcitrans ) Is included, but is not limited to these.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to control pests of the Order Hemiptera. A non-exhaustive list of specific genera includes the genus Aderges spp., The genus Aulacas spp., The genus Aphrophora spp., And the genus Aphis.
spp. ), Bemisia spp., Celoplastes spp., Chionaspis spp., Chrysomphalus spp., Coccus spp., Coccus spp. ), Lepidosaphes spp., Laginotomus spp., Lygus spp., Macrosiphum spp., Nephothetics spp. Philaenus spp., Phytocoris spp., Piezodolus spp., Planococcus spp., Psoidococcus sp. , Saisetia spp., Therioaphis spp., Toumeyella spp., Toxoptera spp., Trialeurodes sp. Genus (Unaspis spp.) Is included, but is not limited to these. A non-exhaustive list of certain species includes Acrosternum hirare, Acyrthosisphon pisum, Aleyrodes proletella, Alleulodes lysperus, Alexus・ Floccosus, Amrasca biguttura biguttura, Aoniziella aurantii, Aphis gosipiis Aulacorthum solani, Bemisia
argentifolii), Bemisia flux value (Bemisia tabaci), Burisusu-Reukoputerusu (Blissus leucopterus), Burakikorinera-aspartic (Brachycorynella asparagi), Bureben'nia Lech (Brevennia rehi), Burebikorine-Burashikae (Brevicoryne brassicae), Karokorisu-Norubegikusu (Calocoris norvegicus) , Seropurasutesu-Rubensu (Ceroplastes rubens), Shimekusu-Hemiputerusu (Cimex hemipterus), Shimekusu-Rekutsurariusu (Cimex lectularius), Daguberutsusu-Fashiatsusu (Dagbertus fasciatus), Jisheropusu-Furukatsusu (Dichelops furcatus), Jiurafisu-Nokushia (Diuraphis noxia), Jiaforina・ Diaphorina citri, Dysaphis plantaginea, Dysdercus sturellus, Edessa Meditabunda (Edess)
a meditabunda, Eriosoma langierum, Eurygaster maria, Eustius heros, Eussistus helus, Eussistus selbus
antonii), Heroperuchisu-Teibora (Helopeltis theivora), Iseria-Purukashi (Icerya purchasi), Ijiosukopusu-Nichizurusu (Idioscopus nitidulus), Lao del fax Sutsuriaterusu (Laodelphax striatellus), Reputokorisa-Oratoriusu (Leptocorisa oratorius), Reputokorisa-Barikorunisu (Leptocorisa varinis), Lygus hesperus, Maconellicoccus hirsutus, Macrosiphum euphorbiae, Macrosiphum euphorbiae, Macrosiphum granarium Tsusu (Macrosteles quadrilineatus), Mahanaruba-Furimubiorata (Mahanarva frimbiolata), Metoporofiumu-Jirozumu (Metopolophium dirhodum), Mikuchisu-Rongikorunisu (Mictis longicornis), Myzus persicae (Myzus persicae), Nefotetikusu-Shinkuchipesu (Nephotettix cinctipes), Neuro Corpus-Rongirosutsurisu (Neurocolpus longirostris), Nezara-Birizura (Nezara viridula), Niraparubata-Rugensu (Nilaparvata lugens), Paruratoria-Peruganjii (Parlatoria pergandii), Paruratoria-Jijifi (Parlatoria ziziphi), Peregurinusu-Maijisu (Peregrinus maidis), Firokusera-Bichiforiae (Phylloxera
vitifoliae), Fisokerumesu-Piseae (Physokermes piceae), Fitokorisu Cal folder Nix (Phytocoris californicus), Fitokorisu-Rerachibusu (Phytocoris relativus), Piezodorusu-Guirujinii (Piezodorus guildinii), Poeshirokapususu-Rineatsusu (Poecilocapsus lineatus), Pusarusu-Bashinikora (Psallus vaccinicola ), Puseudashisuta-Peruseae (Pseudacysta perseae), Puseudo Cox Burebipesu (Pseudococcus bravipes), Quadra spin Geo Tsusu-Perunishiosusu (Quadraspidiotus perniciosus), Roparoshifumu-Maijisu (Rhopalosiphum maidis), Roparoshifumu-Paji (Rhopalosiphum padi), Saisechia-Oreae ( San Jose oleae, Scaptocoris castanea, Pseudococcus graminum, Sitobion avenae, Sogatera fullsifera
furcifera), Trialeurodes vaporariorum, Trialeurodes abutiloneus, Unaspis yanonensis (Unaspis yanonensis not included) and Unaspis yanonensis (Unaspis yanonensis)

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the order Hymenoptera. A non-exhaustive list of specific genera includes the genera Acromylmex spp., Atta spp., Camponotus spp., Diprion spp., Formica spp. .), Monomorium genus (Mo
nomorium spp. ), Neodiprion spp., Pogonomyrmex spp., Polistes spp., Solenopsis spp., Vespula sp. Is included, but not limited to these. A non-exhaustive list of certain species includes Atalia rosae, Atta texana, Iridomyrmex humilis, Monomoriumumumum, Monomoriumumumumumumumum. pharaonis), Sorenopushisu - Invicta (Solenopsis invicta), Sorenopushisu-Geminata (Solenopsis geminata), Sorenopushisu-Moresuta (Solenopsis molesta), Sorenopushisu-Rikuteri (Solenopsis richtery), Sorenopushisu-Kishironi (Solenopsis xyloni) and Tapinoma-Seshire (Tapinoma sessile) Is included, but not limited to these.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress termite pests. A non-exhaustive list of specific genera includes the genera Coptotermes spp., Cornitermes spp., Cryptotermes spp., Heterotermes spp., Kalotermes sp. ), Incistermes spp., Macrotermes spp., Marginitermes spp., Microcellomes spp., Procermes spp., Procornes spp. Includes, but is not limited to, the genus Reticulitermes spp., The genus Schedorhinotermes spp. And the genus Zoothermopsis spp. A non-exhaustive list of certain species includes Copttermes curvignathus, Copttermes frenchi, Copttermes formosanus, Hetertermes aureus, Hetermes aureus (Hetermes). Microtermes obesi, Reticulitermes banyulensis, Reticulitermes glassei, Reticulitermes flavitemes flavipes, Reticulitermes flavipes Reticulitermes hesperus, Reticulitermes santonensis, Reticulitermes speratus, Reticulitermes speratus, Reticulitermes speratus, Reticulitermes stibialis and Reticulitermes stibialis I can't.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the order Lepidoptera. A non-exhaustive list of specific genera includes Agrotis spp. And Agrotis.
spp. ), Argyrotaneia spp., Cacoecia spp., Caloptilia spp., Chilo spp., Chrysodeixis.
spp. ), Colias spp., Crambus
spp. ) Diaphania spp., Diathraea spp., Airias spp., Ephestia spp., Epimecis spp., Feltia spp., Feltia spp. Genus (Gortyna spp.), Helicoverpa spp., Heliosis (Heliosis)
spp. ), Indarbella spp., Lithocollettis spp., Loxagrotis spp., Malakosoma spp., Malacosoma spp., Perizroma spr. The genus Pseudaletia spp., The genus Sesamia spp., The genus Spodoptera spp., The genus Synanthedon spp. And the genus Yponomeuta.
spp. ), Is included, but not limited to these. A non-exhaustive list of certain species includes Achaea janata, Adoxophyes orana, Agrotis ipsilon, Alabama algala seaa (Alabama argilacea). , Amieroshisu-Tsuranshitera (Amyelosis transitella), Anakamuputodesu-Defekutaria (Anacamptodes defectaria), Anarushia-Rineatera (Anarsia lineatella), Anomisu-Saburifera (Anomis sabulifera), anti-calcia-Gematarisu (Anticarsia gemmatalis), Aruchipusu-Arugirosupira (Archips argyrospila), Archips rosana, Argyrotaneia citrana, Autographa gamma, Bonagota cranaodes, Bonagota cranabols , Capua, Rechikurana (Capua reticulana), Karuposhina-Niponenshisu (Carposina niponensis), Kurumechia transformer Versa (Chlumetia transversa), Korisutoneura-Rosaseana (Choristoneura rosaceana), Kuna file potter's wheel Sith Mejinarisu (Cnaphalocrocis medinalis), Konopomorufa-Kuramerera (Conopomorpha Cramella, Cossus cossus, Cydia caryana, Cydia funebrana, Cydia molesta, Cydia molesta, Cydia niglikana, Cydia , Darna diducta, Diatraea saccharalis, Diatraea Guranjiosera (Diatraea grandiosella), Eariasu-Insurana (Earias insulana), Eariasu-Bitera (Earias vitella), Ekujitorofa Au Lancia-Num (Ecdytolopha aurantianum), Erasumoparupusu-Rigunoserusu (Elasmopalpus lignosellus), Ephestia-Kautera (Ephestia cautella), Ephestia · Erutera (Ephestia elutella), Ephestia-Kueniera (Ephestia kuehniella), Epinochia-Aporema (Epinotia aporema), Epifiasu-Posutsubitana (Epiphyas postvittana), Erionota-Surakusu (Erionota thrax), Eupoeshiria-Amubiguera (Eupoecilia ambiguella), Eukusoa-Aukushiriarisu (Euxoa auxiliaris), Graphorita molesta, Hezirepta indicata, Helicovelpa armiera, Helicovelpa armeira, Helicobelpa zea undalis), Kei Feria Rikoperushisera (Keiferia lycopersicella), Reushinodesu-Orubonarisu (Leucinodes orbonalis), Reukoputera-Kofeera (Leucoptera coffeella), Reukoputera-Mariforiera (Leucoptera malifoliella) ,, Robeshia-Botsurana (Lobesia botrana), Rokusagurochisu-Arubikosuta (Loxagrotis albicosta, Limantria discar, Lyonetia clerkela, Mahasena corbetti, Mamethura brushcae (Mamethra) plana), Michimuna-Yunipunkuta (Mythimna unipuncta), Neore Ushino Death Eregantarisu (Neoleucinodes elegantalis), Nimufura-Depunkutarisu (Nymphula depunctalis), Operofutera-Burumata (Operophthera brumata), Osutsurinia-Nubirarisu (Ostrinia nubilalis), Okushijia-Besuria ( Oxydia vesulia), Pandemisu-Serasana (Pandemis cerasana), Pandemisu-Heparana (Pandemis heparana), Papillio-Demodokusu (Papilio demodocus), Pekuchinofora-Goshipiera (Pectinophora gossypiella), Perizuroma-Saushia (Peridroma saucia), Perireukoputera-Kofeera (Perileucoptera coffeella ), Phthrimaea operculella, Phyllocnistis citralla, Pieris rapae, Pratipena skabra (Plathypena) ), Polychrosis viteana, Price endocalpa, Price oleae, Pseudaletia unipunta, Pseudaletia unipuncata, Pseudolia unipuncata ), Shirupofaga-Inserutsurasu (Scirpophaga incertulas), Sesamia-Inferensu (Sesamia inferens), Sesamia-Nonagurioidesu (Sesamia nonagrioides), settler-Nitensu (Setora nitens), Shitotsuroga-Serearera (Sitotroga cerealella), Suparuganoshisu-Pireriana (Sparganothis pilleri ana), Spodoptera exigua, Spodoptera frugiperda, Spodoptera eridania (Spodoptera)
eridania), Tecla basilides, Tineola bisselliella, Trichoplusia ni, Ivy Absolta (Tuta absolta) Is included, but not limited to these.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the order Mallophaga. A non-exhaustive list of specific genera includes the genera Anaticola spp., Bovicola spp., Chelopistes spp., Goniodes sp.
niodes spp. ), The genus Menacanthus spp., And the genus Trichodectes spp., But not limited to these. A non-exhaustive list of certain species includes Bovicola bovis, Bovicola caprae, Bovicola obis, Cellopistes meleagridisis dysgisides melea. , Goniodes gigas, Menacanthus stramineus, Menopon gallinae and Trichodectes canis, but not limited to Trichodectes canis.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the Orthoptera (Orthoptera). A non-exhaustive list of specific genera includes, but is not limited to, the genus Melanoplus spp. And the genus Pterophylla spp. A non-exhaustive list of specific species includes Anables simplex, Gryllotalpa africana, Gryllotalpa australis, Glylotalpa australis, Glylotalpa australalis, Glylotalpa australalis, Glylotalpa australalis, Glylotalpa australis , Locusta migratorya, Microcentrum retinerve, Cristocerca gregaria and Scuderia not limited to scuddia fur.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the order Flea (Order Siphonapptera). A non-exhaustive list of certain species includes Ceratophyllus gallinae, Ceratophyllus niger, Ctenocephalides canis and Ctenocefalides celis -Includes, but is not limited to, iritans.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the order Thrips (Order Thysanoptera). A non-exhaustive list of specific genera includes the genus Cariothrips spp., The genus Frankliniella spp., The genus Scirtotrips spp. And the genus Trips spp. Not limited. A non-exhaustive list of specific species includes Frankliniella fusca, Frankliniella occidentalis, Frankliniella shultzei, Frankliniella shultzei, Frankliniella shultzei. williamsi), Heriosuripusu-fly mole Hui Darisu (Heliothrips haemorrhoidalis), lipid Roman Sri TOPS-Kuruentatsusu (Rhipiphorothrips cruentatus), Shirutosuripusu-Shitsuri (Scirtothrips citri), Shirutosuripusu-Dorusarisu (Scirtothrips dorsalis) and Taeniosuripusu-Roparantenarisu (Taeniothrips rhopalantennalis), Trips hawaiensis, Trips niglopilos, Trips o
Orientalis), slips tabaci), but not limited to these.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of Thysanura. A non-exhaustive list of specific genera includes, but is not limited to, the genus Lepisma spp. And the genus Thermobia spp.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the order Mite (Order Acarina). A non-exhaustive list of specific genera includes Acarus spp., Acculops spp., Boophilus spp., Demodex spp., Dermacentor spp. ), Epitrimers spp., Eriophyes spp., Ixodes spp., Oligonychus spp., Panonychus spp., Panonychus spp. And the genus Tetranychus spp., But not limited to these. A non-exhaustive list of certain species includes Acarapis woodi, Acarus siro, Aceria mangiferae, Acrops licoperus psycles , Aculus schlechtendali, Ambryomma americanum, Brevipalpus obovatus, Brevipalpus foenic Pteronicinus (Dermatophagoides pteronysinus), Eotetranycus carpini, Notoezless cati (Notoedres cati), Oligonychus cous ulmi (Panonychus ulmi), Firokoputsuruta-Oreibora (Phyllocoptruta oleivora), poly file Gota Luso Nemusu-Ratsusu (Polyphagotarsonemus latus), Rhipicephalus-sanguineus (Rhipicephalus sanguineus), Sarukoputesu-Sukabiei (Sarcoptes scabiei), Tegorofusu-Peruseafurorae (Tegolophus perseaflorae), Tetsuranikusu -Includes, but is not limited to, Tetranychus ulticae and Varroa destrudor.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the Order Symphyla. A non-exhaustive list of specific species includes, but is not limited to, Scuitgerella immaculata.

In another embodiment, molecules of formula 1 and / or formula 2 may be used to suppress pests of the C. elegans (Phylum Nematoda). A non-exhaustive list of specific genera includes Aferenchoides spp., Boophilius spp., Criconemella spp., Ditylenchus spp., Heterodera spp.
rodora spp. ), Hirschmanniella spp., Hoploraimus spp., Meloidogyne spp., Pratylenchus spp., Pratylenchus spp., And Radfors sp. do not have. A non-exhaustive list of certain species includes Dirofilaria imitis, Heterodera zeae, Meloidogyne incognita, Meloidogena vicobina cavani ), Radopholus similis and Rotylenchurus reniformis, but not limited to these.

For additional information, see Arnold Mallis, "Handbook of Pest Control-The Behaver, Life History, and Control of Household Pests," 9th Edition, 2004, GI, 2004.

Application C. control of pests in the phylum C. elegans, arthropods and / or phylum Pseudomonas aeruginosa generally means reduction in pest populations, pest activity or both in the presence. this is:
(A) Will the pest population be repelled from where it is?
(B) Can occur when pests are incapacitated in or around the area; or (c) can occur when pests are extinct in or around the area. Of course, a combination of these results can occur. In general, the pest population, activity or both is preferably reduced by more than 50 percent, preferably greater than 90 percent, and most preferably greater than 98 percent. Generally the place is not in or above humans; after all, the place is generally a non-human place.

In another embodiment, the place where the molecule of formula 1 and / or formula 2 is applied may inhabit or become inhabited by pests of the phylum C. elegans, arthropods and / or mollusks. It can be anywhere there or may cross. For example, the place is:
(A) Places where crops, trees, fruits, grains, hooder species, grapes, turf and / or ornamental plants grow;
(B) Where livestock live;
(C) Inside or outside of the building (like where grain is stored);
(D) Building materials used in the building (such as impregnated wood); and (e) can be soil around the building.

Specific crop areas for the use of formulas 1 and / or formula 2 molecules include apples, corn, sunflowers, cotton, soybeans, canola, wheat, rice, great millet, corn, oats, potatoes, oranges, alfalfa, lettuce, etc. Includes areas where strawberry, tomato, corn, millet, pear, tobacco, almond, sugar beet, common bean and other valuable crops are growing or where their seeds will be planted. It is also advantageous to use ammonium sulphate with the molecules of formula 1 and / or formula 2 when growing various plants.

In another embodiment, the molecules of formula 1 and / or formula 2 are generally used in an amount of about 0.0001 grams per hectare to about 5000 grams per hectare to provide inhibition. In another embodiment, the molecules of formula 1 and / or formula 2 are preferably used in an amount of about 0.001 grams per hectare to about 500 grams per hectare. In another embodiment, it is more preferred to use the molecules of formula 1 and / or formula 2 in an amount of about 0.01 grams per hectare to about 50 grams per hectare.

Molecules of formula 1 and / or formula 2 can be used in mixtures or alone or other compounds to enhance plant vitality (eg, to grow better root systems, to withstand stressful growing conditions). May be applied simultaneously or sequentially with. Such other compounds are, for example, compounds that modify plant ethylene receptors, in particular 1-methylcyclopropene (also known as 1-MCP). In addition, such molecules may be used during periods of low pest activity, such as before growing plants begin to produce valuable agricultural products. Such periods include the initial planting period, when pest pressure is usually low.

Molecules of formula 1 and / or formula 2 can be applied to the leaves and fruiting portions of plants to control pests. The pest control agent will be consumed when the molecule comes into direct contact with the pesticide or when the pesticide eats a leaf, fruit mass containing the pest control agent or extruding the sap. Molecules of formula 1 and / or formula 2 can also be applied to soil, and when applied in this way, pests feeding on roots and stems can be suppressed. The roots can absorb the molecule and raise it into the leaf part of the plant to suppress masticatory and sap-eating pests on the ground.

In general, when bait is used, the bait is placed, for example, in the ground where termites can come into contact with and / or be attracted to the bait. The bait can also be applied, for example, to the surface of a building (horizontal plane, vertical plane or slope) where ants, termites, cockroaches and flies can come into contact with the bait and / or be attracted to the bait. The bait can contain molecules of formula 1 and / or formula 2.

Molecules of formula 1 and / or formula 2 can be encapsulated inside the capsule or placed on the surface of the capsule. Capsule sizes can range from nanometer size (diameter about 100-900 nanometers) to micrometer size (diameter about 10-900 microns).

Due to the unique ability of some pest eggs to resist certain pest control agents, repeated application of the molecules of Formula 1 and / or Formula 2 may be desirable for the control of emerging larvae. be.

Utilizing the systemic movement of pest control agents in plants, pests on one part of the plant are applied with molecules of formula 1 and / or formula 2 to different parts of the plant (eg, spraying on one area). Depending on), it may be suppressed. Leaf-eating insects (foliar-), for example by drip irrigation or furrow spraying, by treating the soil with pre-planting or post-planting soil dipping (drench), or by treating the plant seeds before planting. Suppression of irrigation insects) can be achieved.

Seed treatment can be applied to all types of seeds, including those that will germinate plants that have been genetically modified to express special traits. Typical examples are those that express proteins that are toxic to invertible pests such as Bacillus turingiensis or other insecticidal toxins, and herbicide resistance such as "Roundup Ready" seeds. Or those with an "stacked" heterologous gene that expresses insecticidal toxins, herbicide resistance, nutrition-enhancement, drought resistance or any other beneficial trait. Is done. In addition, such seed treatments using the molecules of Formula 1 and / or Formula 2 may further enhance the plant's ability to better tolerate stressful growing conditions. This gives rise to healthier and stronger plants, which can lead to higher yields at harvest. It is generally believed that about 1 gram to about 500 grams of Formula 1 and / or Formula 2 molecules per 100,000 seeds provide excellent benefits, and about 10 grams to about 100 grams per 100,000 seeds. The amount of grams is likely to give better benefits, and the amount of about 25 grams to about 75 grams per 100,000 seeds is likely to give even better benefits.

Plants genetically modified to express special traits such as Bacillus turingiensis or other herbicide toxins or those that develop herbicide resistance or either insecticidal toxins, herbicide resistance, nutritional enhancement or others It should be readily apparent that molecules of formula 1 and / or formula 2 may be used in or around those having "stacked" heterologous genes that express these beneficial traits. ..

Molecules of formula 1 and / or formula 2 may be used to control endoparasites and ectoparasites in the veterinary department or in the field of non-human animal rearing. Molecules of formula 1 and / or formula 2 can be administered orally in the form of tablets, capsules, beverages, granules, for example, in the form of soaking, spraying, bowling on, spotting on and spraying. It is applied by skin application, as well as by parenteral administration, for example in the form of injection.

Molecules of formula 1 and / or formula 2 may also be used advantageously in livestock breeding, such as cattle, sheep, pigs, chickens and geese. They may also be used advantageously in pets such as horses, dogs and cats. Certain pests to control are fleas and mites that are annoying to such animals. Suitable preparations are orally administered to animals with drinking water or feed. Suitable dosages and preparations are species dependent.

Molecules of formula 1 and / or formula 2 may also be used to control parasites, especially intestines, in the animals listed above.

Molecules of formula 1 and / or formula 2 may be used in therapeutic methods for human health care. Such methods include, but are not limited to, oral administration and dermal application in the form of tablets, capsules, beverages, granules, for example.

Pests around the world have moved to new environments (for such pests) and have since become new invasive species in such new environments. Molecules of formula 1 and / or formula 2 may also be used to suppress such new invasive species in such new environments.

Molecules of formula 1 and / or formula 2 are areas where plants such as crops are growing (eg, pre-planting, planting, pre-harvest) and have low levels of pests that can commercially damage such plants (eg, pre-planting, pre-harvesting, pre-harvesting). It may also be used in the region (even if it does not actually exist). The use of such molecules in such regions is to benefit the plants growing in said regions. Such benefits include improved plant health, increased plant yields (eg, increased biomass and / or increased content of valuable components), improved plant vitality (eg, improved plant growth and / or). More green leaves), improved plant quality (eg, improved content or composition of certain components) and may include, but are limited to, improved resistance of the plant to abiotic and / or biological stress. I can't.

Before commercial use or sale of pest control agents, such pest control agents are a lengthy evaluation process by various government authorities (local, regional, state, national and international). Go through. Huge data requirements are manifested by regulatory agencies and must be addressed through data generation and submission by product registrants or third parties on behalf of product registrants, often using computers connected to the World Wide Web. Must be. These government authorities then review such data and grant product registration approval to potential users or sellers once a safety decision is concluded. Subsequently, such users or sellers may use or sell such pest control agents in the area where product registration is accepted and supported.

Molecules according to formulas 1 and / or formula 2 can be tested to determine their efficacy against pests. Further mode of action studies can be performed to determine if the molecule has a different mode of action from other pest control agents. After that, such acquired data can be disseminated to a third party by means of the Internet or the like.

The headings in this document are for convenience only and should not be used to describe any part of this document.

Combinations In another embodiment of the invention, molecules of formula 1 / formula 2 may be used in combination with one or more active ingredients (in a composition mixture, or as simultaneous or sequential application).

In another aspect of the invention, one or more molecules of formula 1 / formula 2 having the same, similar, but more likely, different MoA to the MoA of the molecule of formula 1 / formula 2, respectively. May be used in combination with the active ingredient of (as in a compositional mixture or for simultaneous or sequential application).

In another embodiment, the molecule of formula 1 / formula 2 is mite-killing, algae-killing, bird-killing, bacterial-killing, bactericidal / mold-killing, herbicidal, insecticidal, mollusc-killing, nematode-killing. , May be used in combination with one or more molecules that are nematode and / or virus-killing (in compositional mixtures, or for simultaneous or sequential application).

In another embodiment, the molecule of formula 1 / formula 2 is used as a feeding inhibitor, avian repellent, a chemical fertility agent, a herbicide antidote, an insect attractant, an insect repellent, a mammal repellent, a mating disruptor, a plant activation. It may be used in combination with one or more molecules that are agents, plant growth regulators and / or synergists (such as in compositional mixtures or for simultaneous or sequential application).

In another embodiment, the molecules of Formula 1 / Formula 2 may be used in combination with one or more biopesticides (such as in a composition mixture or for simultaneous or sequential application).

In another embodiment, the combination of the molecule of Formula 1 / Formula 2 and the active ingredient may be used in various weight ratios in the pest control composition. For example, in a two-component mixture, the weight ratio of the molecule to the active ingredient of Formula 1 / Formula 2 and the weight ratio in Table A may be used. However, a weight ratio of less than about 10: 1 to about 1:10 is generally preferred. It may be preferable to use a mixture of 3, 4, 5, 6, 7 or more components comprising the molecule of formula 1 / formula 2 and two or more additional active ingredients.

The weight ratio of the molecule to the active ingredient of Formula 1 / Formula 2 may be expressed as X: Y, where X is the weight portion of the molecule of Formula 1 / Formula 2 and Y is the weight portion of the active ingredient. be. The numerical range of the weight part with respect to X is 0 <X < 100, and the weight part with respect to Y is 0 <Y < 100, and the graph is shown in Table B.
Shown in. As a non-restrictive example, the weight ratio of the molecular to active ingredient of Formula 1 / Formula 2 may be 20: 1.

The range of the weight ratio of the molecule to the active ingredient of the formula 1 / formula 2 may be expressed as X ₁ : Y ₂ to X ₂ : Y ₂ , where X and Y are defined as described above.

In one embodiment, the range of weight ratios may be X ₁ : Y ₁ to X ₂ : Y ₂ , where X ₁ > Y ₁ and X ₂ <Y ₂ . As a non-restrictive example, the range of the weight ratio of the molecule to the active ingredient of the formula 1 / formula 2 may be 3: 1 to 1: 3 including the end point.

In another embodiment, the range of weight ratios may be X ₁ : Y ₁ to X ₂ : Y ₂ , where X ₁ > Y ₁ and X ₂ > Y ₂ . As a non-restrictive example, the range of the weight ratio of the molecule to the active ingredient of the formula 1 / formula 2 may be 15: 1 to 3: 1 including the end point.

In another embodiment, the range of weight ratios may be X ₁ : Y ₁ to X ₂ : Y ₂ , where X ₁ <Y ₁ and X ₂ <Y ₂ . As a non-restrictive example, the range of the weight ratio of the molecule to the active ingredient of the formula 1 / formula 2 may be about 1: 3 to about 1:20 including the end points.

It is included that some weight ratios of the molecular to active ingredients of Formula 1 / Formula 2 shown in Tables A and B may be synergistic.

The compounds of the present invention may be useful in improving the vitality of crops. This method comprises formula 1 in an amount (ie, a biologically effective amount) sufficient to achieve the desired plant vitality effect on the crop (eg, leaves, flowers, fruits or roots) or the seed on which the crop grows. / Includes contact with the compound of formula 2. Typically, the compounds of formulas 1 and 2 are applied in the prepared compositions. The compounds of formulas 1 and 2 are often applied directly to the crop or its seeds, which allows the location of the crop, i.e. the environment of the crop, in particular the compounds of formulas 1 and 2 to move to the crop. It can also be applied to parts of the environment that are close enough to. Locations associated with this method most commonly include growth media (ie, media that nourish the plant), typically the soil in which the plant grows. Thus, the treatment of the crop to improve the vitality of the crop comprises contacting the crop, and then the seed on which the crop grows, or the location of the crop with a biologically effective amount of a compound of Formula 1 / Formula 2.

Increased crop vitality can result in one or more of the following effects observed: (a) Optimal crop growth as demonstrated by excellent seed germination, emergence and stand. (B) Rapid and vigorous leaf growth (eg measured by leaf area index), plant height, number of splits (eg for rice), root mass and crop plant mass (vegetative mass). ) Enhanced crop growth as indicated by the overall dry weight; (c) time to flowering, duration of flowering, number of flowers, total biomass accumulation (ie yield) and / or fruit or grain of the product Improved crop yield as indicated by fruit or grain marketability of production (ie, quality of crop); (d) withstand plant disease infections and the spread of mitotic, nematode or soft animal pests Or the enhanced ability of the crop to prevent them; as well as (e) the improved ability of the crop to withstand environmental stresses such as extreme temperature, suboptimal humidity or exposure to phytotoxic chemicals.

The compounds of the present invention enhance the vitality of treated plants compared to untreated plants by killing or otherwise preventing herbivorous inverteous pests in the plant's environment. Can be improved. Without suppression of such phytophagous invertebrate pests, pests reduce plant vitality by consuming plant tissues or sap or transmitting phytopathogens such as viruses. Even in the absence of phytophagous invertebrate pests, the compounds of the invention may improve plant vitality by altering plant metabolism. In general, crop vitality grows in a non-ideal environment, that is, an environment that includes one or more aspects that are detrimental to the plant's achievement of the full genetic potential of the plant in the ideal environment. In some cases, treatment of the plant with the compounds of the invention will be most significantly improved.

Of note is this method for improving crop vitality when the crop grows in an environment containing herbivorous invertebrate pests. Also noteworthy is this method for improving crop vitality when the crop grows in an environment free of herbivorous invertebrate pests. Also noteworthy is this method for improving crop vitality when the crop grows in an environment containing less than the ideal amount of water to support the growth of the crop. This method for improving the vitality of the crop when the crop is rice is noteworthy. Also noteworthy is this method for improving the vitality of crops when the crop is corn. Also noteworthy is this method for improving crop vitality when the crop is soybean.

Growth modifiers such as insecticides, bactericidal and fungicides, nematode pesticides, bacterial killers, acaricides, herbicides, herbicides detoxifiers, insect dehulling inhibitors and rooting stimulants. , Chemical fertility agents, information chemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or one or more other species including insecticidal bacteria, viruses or fungi / molds. It can also be mixed with biologically active compounds or agents to form multi-component pesticides that provide a much wider range of agricultural and non-agricultural utility. Thus, the present invention comprises at least one additional component and at least one addition selected from the group consisting of biologically effective amounts of compounds of Formula 1 / Formula 2, surfactants, solid diluents and liquid diluents. Also related to compositions containing biologically active compounds or agents. For the mixtures of the invention, other biologically active compounds or agents can be prepared with the compound, including compounds of formulas 1 and 2, to form premixes, or others. The biologically active compound or agent of is prepared separately from the compound containing the compounds of formula 1 / formula 2 and the two preparations are combined together prior to application (eg in a spray tank) or also. It can be applied continuously.

Examples of such biologically active compounds or agents for which the compounds of the invention can be prepared together are abamectin, acephate, acequinosyl, acetamipride, acrinathrin, asinonapill, afidopyropen ([(3S, 4R, 4aR,, 6S, 6aS, 12R, 12aS, 12bS) -3-[(Cyclopropylcarbonyl) oxy] -1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy- 4,6a, 12b-trimethyl-11-oxo-9- (3-pyridinyl) -2H, 11H-naphtho [2,1-b] pyrano [3,4-e] pyran-4-yl] methylcyclopropanecarboxy Rate), amide flumet, amitraz, avermectin, azadirachtin, azinephosmethyl, benfracarb, benzlutap, benzpyrimoxane, bifentrin, biphenazate, bistrifluron, borate, buprofezin, kazusaphos, carbaryl, carbofuran, cartap, (Carzol), chloranthraniliplol, chlorphenapir, chlorfluazuron, chlorpyriphos, chlorpyriphosmethyl, chromaphenodide, clofentedin, clothianidin, cyantranliprol (3-bromo-1- (3-chloro-2-pyridinyl)) -N- [4-cyano-2-methyl-6-[(methylamino) carbonyl] phenyl] -1H-pyrazole-5-carboxyamide), cyclaniliprol (3-bromo-N- [2-bromo-] 4-Chloro-6-[[(1-cyclopropylethyl) amino] carbonyl] phenyl] -1- (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxyamide), cycloprothrin, cycloxapride ( cycloxoprid) ((5S, 8R) -1-[(6-chloro-3-pyridinyl) methyl] -2,3,5,6,7,8-hexahydro-9-nitro-5,8-epoxy-1H- Imidazo [1,2-a] azepine), cypermethrin, cypermethrin, beta cypermethrin, cypermethrin, gamma cypermethrin, lambda cypermethrin, cypermethrin, alpha cypermethrin, zeta cypermethrin, siromadin, deltamethrin, diafenthirone. , Diazinone, Dieldrin, Diflubenzron, Dimefluthrin, Dimehypo, Dimet Ate, dinotefuran, diophenolan, emamectin, endosulfan, esphenvalerate, ethiprol, etofemprox, etoxazole, fenbutatin oxide, phenothiolthione, phenothiocarb, phenoxycarb, fenpropatrin, fenvalerate, fipronil, fromhetin (2-ethyl-3,7) -Dimethyl-6- [4- (trifluoromethoxy) phenoxy] -4-quinolinylmethyl carbonate), fronicamid, fluazindidine, flubenzamide, flucitrinate, fluphenerim, fluphenoxlon, fluphenoxystrobin ( Methyl (αE) -2-[[2-chloro-4- (trifluoromethyl) phenoxy] methyl] -α- (methoxymethylene) benzene acetate), fluene sulfone (5-chloro-2-[(3,4)) 4-Trifluoro-3-buten-1-yl) sulfonyl] thiazole), fluhexafone, fluphyllol (1- [2,6-dichloro-4- (trifluoromethyl) phenyl] -5-[(2-methyl) -2-Propen-1-yl) amino] -4-[(trifluoromethyl) sulfinyl] -1H-pyrazole-3-carbonitrile), flupyraziflon (4-[[(6-chloro-3-pyridinyl) methyl]] (2,2-Difluoroethyl) Amino] -2 (5H) -Flanon), flypyrimin, fluvalinate, taufluvalinate, honophos, formethanate, hostiazete, halophenozide, heptafluthrin ([2,3,5,) 6-Tetrafluoro-4- (methoxymethyl) phenyl] methyl 2,2-dimethyl-3-[(1Z) -3,3,3-trifluoro-1-propen-1-yl] cyclopropanecarboxylate), Hexaflumuron, hexithiazox, hydramethylnone, imidacloprid, indoxacarb, insecticidal soap, isofenphos, ruphenurone, malathion, meperfluthrin ([2,3,5,6-tetrafluoro-4- (methoxymethyl) phenyl] methyl ([2,3,5,6-tetrafluoro-4- (methoxymethyl) phenyl] methyl ( 1R, 3S) -3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropanecarboxylate), metaflumison, metaldehide, metamidophos, methidathione, methiocarb, mesomil, metoprene, methoxychlor, methoxyphenozide, metoflutrin, monochromotophos, Monofluorotrin (mon) offluorothrin) ([2,3,5,6-tetrafluoro-4- (methoxymethyl) phenyl] methyl 3- (2-cyano-1-propen-1-yl) -2,2-dimethylcyclopropanecarboxylate) , Nicotin, Nitempirum, Nitiazine, Novallon, Noviflumron, Oxamil, Oxazosulfyl, Palatin, Palatin Methyl, Permethrin, Holate, Hosalon, Hosmet, Phosphamiden, Pyrimicurve, Profenophos, Profluthrin, Propargit, Protrifenbut, Piflubumid (1, 3,5-trimethyl-N- (2-methyl-1-oxopropyl) -N- [3- (2-methylpropyl) -4- [2,2,2-trifluoro-1-methoxy-1-(2,2-trifluoro-1-methoxy-1-) Trifluoromethyl) ethyl] phenyl] -1H-pyrazol-4-carboxyamide), pimetrodin, pyrafluprol, pyrethrin, pyridaben, pyridalyl, pyrifluquinazone, pyriminostrobin (methyl (αE) -2-[[[2- [(2,4-dichlorophenyl) amino] -6- (trifluoromethyl) -4-pyrimidinyl] oxy] methyl] -α- (methoxymethylene) benzene acetate), pyriprol, pyriproxyfen, rotenone, ryanodine , Silafluofen, spinnetram, spinosad, spirodiclophen, spirodion, spiromethifene, spirotetramato, sulfofos, sulfoxaflor (N- [methyl oxide [1- [6- (trifluoromethyl) -3-pyridinyl] ethyl) ] -Λ ⁴ -Sulfanilidene] cyanamide), tebuphenozide, tebufenpyrado, teflubenzlone, tefluthrin, terbuphos, tetrachlorbinphos, tetramesulin, tetramethylfluthrin ([2,3,5,6-tetrafluoro-4- (methoxymethyl)) Methyl 2,2,3,3-tetramethylcyclopropanecarboxylate), tetraniliprol, thiacloprid, thiamethoxam, thiodicalve, thiosultap sodium, thioxazaphen (3-phenyl-5- (2-thienyl) -1, 2,4-oxadiazole), tolfenpyrado, tralomethrin, triazamate, trichlorfon, triflumezopyrim (2,4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl] -2 H-pyrido [1,2-a] pyrimidinium internal salt), triflumuron, ticropyrazoflor, Bacillus turingiensis deltaendotoxin, insect pathogenic bacteria, insect pathogenic viruses and insecticidal insecticides such as fungi It is an agent.

Notable are abamectin, acetamiprid, acrinathrin, asinonapil, afidopyropen, amitraz, avelmectin, azadilactin, benfracarb, benzlutap, benzpyrimoxane, bifentrin, buprofezin, kazusaphos, carbalyl, cartap, chloranthraniliprol, chlorphenliprol. Crossianidin, thiamethoxam, cyclaniliprol, cycloprothrin, cypermethrin, beta-cypermethrin, cypermethrin, gamma cypermethrin, lambda cypermethrin, cypermethrin, alpha cypermethrin, zeta cypermethrin, siromadin, deltamethrin, dildoline. , Dinotefuran, diophenolan, emamectin, endosulfan, esphenvalerate, ethiprol, etofenprox, etoxazole, fenitrothione, phenothicarb, phenoxycarb, fenvalerate, fipronil, fromotkin, flonicamide, flubendiamide, fluphenoxlone, fluphenoxystron Flufensulfone, fulpiroll, flupyraziflon, flupyrimin, fluvalinate, formethanate, hostiazeto, heptamethrin, hexaflumron, hydramethylnone, imidacloprid, indoxacarb, ruphenurone, meperfluthrin, metafluthrin, metafluthrin, metafluthrin , Metoprene, methoxyphenozide, metoflutrin, monofluorotrin, nitempirum, nithiazine, novallon, oxamil, oxazosulfyl, pifrubmid, pymetrodin, pyrethrin, pyridaben, pyridalyl, pyriminostrobin, pyriproxyfen, lianodine, spinnetram, spinosad, spiro Diclofen, spiromesiphen, spiropidion, spirotetramato, sulfoxaflor, tebuphenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicalve, thiosultap sodium, tralomethrin, triazamate, triflumezopyrim, triflumuron Insecticides such as Sozoflor, Bacillus cypermethrinsis deltaendotoxin, all strains of Bacillus cypermethrinsis and all strains of nuclear polymorphic disease virus.

One embodiment of a biological agent for mixing with the compounds of the invention includes insect pathogenic bacteria such as Bacillus turingiensis and the CellCap® method (CellCap®, MVP®. MVP® and MVPII® are encapsulated such as MVP® and MVPII® bioinsecticides manufactured by Mycogen Corporation, Indianapolis, Indiana, USA). Bacillus turlingiensis delta-endotoxin; green muscarin, fungus-like entomopathogenic fungi, mold; as well as bacrovirus, helicoverpa-zea nuclear polymorphic disease virus (HzNPV), anagrapha farcifera nucleus Insect-pathogenic (both naturally occurring and recombinant) viruses, including nuclear polymorphic disease virus (NPV) such as polymorphic disease virus (AfNPV); and Sijia pomonella granulosis virus (CpGV). Granule disease virus (GV) such as.

Of particular note are combinations in which other invertebrate pest suppressant active ingredients belong to different chemical types or have different sites of action than the compounds of Formula 1 / Formula 2. In some cases, combination with at least one other invertebrate pest suppressant active ingredient with a similar range of inhibition but different sites of action may be particularly advantageous for the management of resistance. Thus, the compositions of the invention are biologically effective amounts of at least one additional invertebrate pest control active ingredient having a similar range of suppression but belonging to different chemical types or having different sites of action. Can be further included. These additional biologically active compounds or agents include carbamates, mesomil, oxamil, thiodicalve, triazamates and organic phosphates, acetylcholinesterase (AChE) inhibitors such as chlorpyriphos; cyclodiene, dildoline and endosulfan as well. GABAergic chlorine channel antagonists such as phenylpyrazoles, ethiprols and fipronils; pyrethroids, bifenthrin, cifluthrin, beta sifluthrin, sihalothrin, lambda sihalothrin, cypermethrin, deltamethrin, dimefluthrin, esphenvalerate, metoflutrin and profluthrin. Sodium channel modulators such as; neonicotinoids, acetamiprids, clothianidins, cycloxaprides, dinotefuran, flupyrimin, imidacloprid, imidacrotis; nitempyram, nitiazine, paichongging, thiacloprid and thiamethoxam; And nicotinic acetylcholiner receptor (nAChR) agonists such as mesoionic compounds such as triflumesopyrim; nicotinic acetylcholinester (nAChR) allosteric activators such as spinosins, spinnetram and spinosad; avelmectins, abamectin, Chlorine channel activators such as emamectin, milbemectin, repimectin, moxidectin, milbemycin oxime; immature hormone analogs such as diophenolan, metoprene, phenoxycarb and pyridoxyfene; pymetrodin, pyrifluquinazone and afidopyropenmite Growth inhibitors such as chord organ TRPV channel modulators, clofentedin, difluorovidazine, hexitiazox and etoxasol; inhibitors of mitocholinester ATP synthase such as propargit; oxidative phosphorylation through disruption of proton gradients such as chlorphenapir Ucoupler; nicotinic acetylcholine receptor (nAChR) channel blockers such as nereistoxin analogs, cartap; benzoylurea, fluphenoxlon, hexaflumron, ruphenuron, novallon, nobiflumron and triflumron Inhibitors of chitin biosynthesis such as buprofezin; dipteran dehulling disruptors such as siromadin; ecdison receptor agonists such as diacylhydrazines, methoxyphenodides and tebufenodides; octopamine receptor agonists such as amitraz; Mitochondrial Complex III Electron Transport Inhibitors; Mitochondrial Complex I Electron Transport Inhibitors Like Pyridaben; Voltage-Dependent Sodium Channel Blockers Like Indoxacarb and Metaflumison; Tetoronic Acids and Tetraminic Acids, Spirodiclofen , Inhibitors of acetyl CoA carboxylase such as spiromesiphen, spiropidion, AC-118 and spirotetramato; mitochondrial complex II electron transfer inhibitors such as β-ketonitriles, sienopyraphen and siflumethofen; anthranilate diamides, clo Lianidin receptor modulators such as lantraniriplol, cyantraniliplol, tetraniliprol, cyhalodiamide and cyantraniriplol, diamides such as flubenzamide and lianodine receptor ligands such as lianodine; String sound organ modulators such as: Asinonapill, Azadilactin, Benzpyrimoxane, Biphenazate, Frometkin, Fulhexaphone, Oxazosulfyl, Pyridaryl and Tyclopyrazoflor. Unmodified compounds; microbial disruptors of the intestinal midgut membrane such as Bacillus turingiensis and the delta-endotoxins and Bacillus sphaericus they produce; and nuclear polymorphic disease virus (NPV) and others. Includes, but is not limited to, biological agents including, but not limited to, naturally occurring or genetically modified insecticidal viruses.

Further examples of biologically active compounds or agents for which the compounds of the invention can be prepared together are: asibenzoral S-methyl, aldimorph, amethoctrazine, aminopyridene, amysulfrom, anilazine, azaconazole, azoxistrovine, Benalaxil (including Benalaxil M), benodanyl, benomil, benchavaricarb (including benchavaricalbuisopyrropill), benzobindiflupill, betoxazine, vinapacryl, biphenyl, bitertanol, bixaphen, blasticidin S, boscalid, bromco Nazole, bupilimate, butiobate, cardonone, carpropamide, captafol, captan, carbendazim, chloroneb, chlorotalonyl, closolinate, copper hydroxide, copper oxychloride, copper sulphate, spumoxystrobin, siazophamid, siflufenamide, simoxanyl, cyproconazole, Cyprozinyl, Diclobenazox, Diclofluanide, Diclosimet, Dichromedin, Dichloran, Dietofencarb, Diphenoconazole, Diflumethrim, Dimethyrimol, Dimethtomorph, Zimoxystrobin, Diniconazole (including Diniconazole M), Dinocup, Dipymethitron, Dithianone Dodin, econazole, etaconazole, edifenphos, enoxastrobin (also known as enestrovulin), epoxyconazole, etaboxam, etilimol, etridiazol, famoxadon, fenamiden, phenaminestrobin, phenalimol, fenbuconazole. , Fenfuram, fenhexamide, phenoxanyl, fenpicronyl, fenpicoxamide, fenpropidine, fenpropimorph, fenpyrazamine, fentinacetate, fentinhydroxyd, furbam, ferlimzone, frometkin, florylpicoxamide, fluazinum, fludioxonyl , Fluphenoxystrobin, fluindapyl, flumorph, fluopicolid, fluopimomid, fluopyram, fluoxastrobin, flukinconazole, flusilazole, flusulfamide, fluthianyl, flutranyl, flutriahole, fluxapyroxado, holpet, phthalide. Also known as), fuberidazole, flaluxil, copper Lametopil, hexaconazole, himexazole, guazatin, imazalyl, imibenconazole, iminoctadin albesilate, iminoctadine triacetate, impilfluxam, iodicarb, ipconazole, ipfentrifluconazole, ipfluphenokin, isophytamide , Isoflusiplum, Iprobenphos, Iprodion, Iprovaricarb, Isoprothiolan, Isopyrazam, Isothianyl, Kasgamycin, Cresoximemethyl, Manzeb, Mandipropamide, Mandestrobin, Manneb, Mapanipyrin, mefentrifluconazole, Mefentrifluconazole, Mefentrifluconazole Metalaxil M / including mephenoxam), metconazole, metasulfocarb, methylam, metminostrobin, metrafenone, methyltetraplol, microbutanyl, naphthitine, neo-assozin (ferric methanealsonate) , Nuarimol, octylineone, offrace, orythastrobin, oxadixil, oxathiapiproline, oxolinic acid, oxpoconazole, oxycarboxyne, oxytetracycline, penconazole, pencyclon, penflufen, penthiopyrado, perfurazoate, phosphorous acid (its salt) , For example, including phostyl-alluminm), picarbutratox, picoxystrobin, piperaline, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinadide, proquinadide. Oconazole, Pydiflumethofen, Pyracrostrobin, Pyrametstrobi, Pyraoxystrobin, Pyrapropoin, Pyradiflumid, Pyrazophos, Pyribencarb, Pyributacarb, Pyriphenox, Pyriophenone, Pirisoxazole, Pyridaxazole , Pyrphenox, Pyrroln
Itrin), pyroquilon, quinconazole, quinmethionate, quinofumerin, quinoxyphene, quintozen, silthiofam, sedaxan, simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole, tebuflokin, teclophthalam, teclofthalam , Tetraconazole, thiabendazole, thifluzamide, thiophanate, thiophanate-methyl, thiuram, thiazinyl, turquophosmethyl, tolprocarb, trifluandid, triazimephon, triazimenol, trialimol, triazoxide, tribasic copper sulfate, triclopyricalbu , Tridemorph, trifloxystrobin, triflumizole, trimopramide tricyclazole, triforine, triticonazole, uniconazole, varidamycin, varifenalate (also known as varifenal, variphenal). , Bactericidal and fungicides such as dilam and zoxamide; fluorium, spirotetramato, thiodicalve, hostizet, abamectin, iprodion, fluenesulfone, dimethyldisulfide, thioxazaphen, 1,3-dichloropropene (1,3-D), carbam (Sodium and potassium), Dazomet, chloropicrin, phenamiphos, etoplophos, cazusaphos, terbuphos, imiciaphos, oxamil, carbofuran, thioxazaphen, Bacillus filmus and pasteuria nishizawae insecticides. Bactericidal agents such as streptomycin; Amitraz, quinomethionate, chlorbendilate, sihexatin, dichoform, dienochlor, etoxazole, phenazakin, fenbutatin oxide, fenpropatrin, phenpyroximate, hexithiazox, propargit, pyridaben and tebufenpyrado. be.

In some cases, a combination of a compound of the invention with another biologically active (especially invertent pest suppressor) compound or agent (ie, active ingredient) produces a greater (ie, synergistic) effect than additive. be able to. It is always desirable to reduce the amount of active ingredient released into the environment while ensuring effective pest control. If the synergistic action of the invertebrate pest control active ingredient occurs at an application rate that gives an agriculturally satisfactory level of invertebrate pest control, such a combination is for reduced crop production costs and environmental burden. Can be advantageous.

The compounds of the invention and compositions thereof can be applied to plants genetically transformed to express proteins toxic to invertic pests (such as Bacillus turingiensis delta-endotoxin). .. Such applications provide broader plant protection and may be advantageous for resistance management. The effects of the invertebrate pest-suppressing compounds of the present invention, applied externally applied, may be synergistic with the toxin proteins expressed.

General references for these agricultural protective agents (ie, pesticides, fungicides / fungicides, nematodes, acaricides, herbicides and biological agents) include The Pesticide Manual, 13th Edition, C.I. D. S. Tomlin, Ed. , British Crop Protection Council, Farnham, Surrey, U.S.A. K. , 2003 and The BioPesticide Manual. 2nd ^Edition , L. G. Copping, Ed. , British Crop Protection Council, Farnham, Surrey, U.S.A. K. , 2001 is included.

The compounds of the invention are combined or prepared with polynucleotides including, but not limited to, DNA, RNA and / or chemically modified nucleotides, below the genetically induced transcripts that provide an insecticidal effect. The amount of a particular target can be affected through regulation, obstruction, suppression or silencing.

In embodiments where one or more of these various mixed partners are used, the weight ratio of these various mixed partners (in total) to Formula 1 / Formula 2 compounds is typically from about 1: 3000 to about 3000. It is 1. Of note is a weight ratio of about 1: 300 to about 300: 1 (eg, a ratio of about 1:30 to about 30: 1). One of ordinary skill in the art can readily determine the biologically effective amount of active ingredient required for the desired range of biological activity through simple experiments. It will be clear that the inclusion of these additional components can extend the range of suppressed invertebrate pests beyond the range suppressed solely by the compounds of formulas 1 and 2.

Table C lists specific combinations of compounds of Formula 1 / Formula 2 exemplifying the mixtures, compositions and methods of the invention with other invertebrate pest suppressants. The first column of Table C lists specific invertebrate pest suppressants (eg, "abamectin" in the first row). The second column of Table C lists the mode of action (if known) or chemical type of invertebrate pest suppressants. The third column of Table C lists aspects of the range of weight ratios with respect to the rate at which the invertent pest suppressant can be applied to the compounds of formula 1 / formula 2 (eg, abamectin vs. formula 1 / formula by weight). "50: 1 to 1:50" of the compound of 2). Thus, for example, the first row of Table C specifically discloses that the combination of the compound of formula 1 / formula 2 and abamectin can be applied in a weight ratio of 50: 1 to 1:50. The remaining rows in Table C should be interpreted similarly. More notably, Table C lists specific combinations of compounds of formulas 1 and 2 exemplifying the mixtures, compositions and methods of the invention with other invertebrate pest suppressants and rates of application. Includes additional aspects of the range of weight ratios with respect to.

Table section

Molecules (compounds) according to Formulas 1 and / or Formula 2 disclosed herein are tested to determine their efficacy against pests, which are generally A and / or. Shows activity within B category.

Claims (14)

The following equation ("Equation 1 " or "Equation 2")

[During the ceremony:
(A) Ar ¹ is selected from (1) furanyl, phenyl, pyridadinyl, pyridyl, pyrimidinyl or thienyl or (2) substituted furanyl, substituted phenyl, substituted pyridadinyl, substituted pyridyl, substituted pyrimidinyl or substituted thienyl.
Here, the substituted furanyl, the substituted phenyl, the substituted pyridadinyl, the substituted pyridyl, the substituted pyrimidinyl and the substituted thienyl are H, F, Cl, Br, I, CN, NO ₂ , (C ₁ − C ₈ ) alkyl, (C ₁ −. C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) halo alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) alkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C1 _- C8) alkyl, C ₍ O) O- (C1 _- C8) alkyl, C ₍ O)-(C3 _- C8) cycloalkyl, C ₍ O) ) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl -O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl- It has one or more substituents independently selected from C (O) O- (C1 _- C ₈ ) alkyl, phenyl and phenoxy.
Here, each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl and phenoxy substituents are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ) alkyl, (C ₁ ). -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) haloalkoxy, (C ₂ -C ₈ ) alkoxy, (C ₂ -C ₈ ) ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C) ₁ -C ₈ ) haloalkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O -(C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) haloalkyl, C (O)-(C ₃ -C ₈ ) ) Cycloalkyl, C ₍ O) O- ₍ C3 _- C8) cycloalkyl, C ₍ O)-( _{C2 -} C8) alkoxy, C (O) O- (C2-C8) alkoxy, ( C1 _- C8) Alkoxy-O- (C1 _- C8) Alkoxy, ₍ C1 _- C8) Alkoxy-S ₍ O) _n- (C1 _- C8) Alkoxy, _{C (} O)-(C) It may be substituted with one or more substituents independently selected from the group consisting of ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl and phenoxy;
(B) Het is a 5- or 6-membered saturated or unsaturated heterocyclic ring containing one or more heteroatoms independently selected from nitrogen, sulfur or oxygen, where Ar ¹ and Ar. The ^two are not orthos to each other (although they are 1,3 in the case of 5-membered rings and they are 1,3 or 1,4 in the case of 6-membered rings, so they may be meta or para. Yes), and here the heterocyclic ring is also H, F, Cl, Br, I, CN, NO ₂ , oxo, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C). ₁ -C ₈ ) alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) Alkyne, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) Alkyne-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) Alkyne, C (O) O- (C _1- ) C ₈ ) alkyl, C (O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- Selected independently from the group consisting of (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl and phenoxy. It may be substituted with one or more substituents,
Here, each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl and phenoxy substituents are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ) alkyl, (C ₁ ). -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) haloalkoxy, (C ₂ -C ₈ ) alkoxy, (C ₂ -C ₈ ) ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C) ₁ -C ₈ ) haloalkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O -(C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) haloalkyl, C (O)-(C ₃ -C ₈ ) ) Cycloalkyl, C ₍ O) O- ₍ C3 _- C8) cycloalkyl, C ₍ O)-( _{C2 -} C8) alkoxy, C (O) O- (C2-C8) alkoxy, ( C1 _- C8) Alkoxy-O- (C1 _- C8) Alkoxy, ₍ C1 _- C8) Alkoxy-S ₍ O) _n- (C1 _- C8) Alkoxy, _{C (} O)-(C) It may be substituted with one or more substituents independently selected from the group consisting of ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl and phenoxy;
(C) Ar ² is selected from (1) furanyl, phenyl, pyridadinyl, pyridyl, pyrimidinyl or thienyl or (2) substituted furanyl, substituted phenyl, substituted pyridadinyl, substituted pyridyl, substituted pyrimidinyl or substituted thienyl.
Here, the substituted furanyl, substituted phenyl, substituted pyridadinyl, substituted pyridyl, substituted pyrimidinyl and substituted thienyl are H, F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ -C ₈ ) alkyl. , (C ₁ -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) halo alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) alkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) ) Alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C ₃ -C ₈ ) cyclo Alkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ ) -C ₈ ) Alkyl-O- (C ₁ -C ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-S (O) _n- (C ₁ -C ₈ ) Alkyl, C (O)-(C _1- ) C ₈ ) Alkyl-C
(O) O- (C1 _- C8) has _one or more substituents independently selected from alkyl, phenyl and phenoxy.
Here, each alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl, phenyl and phenoxy substituents are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ). Alkyne, (C1 _- C8) haloalkyl, ₍ C3 _- C8) cycloalkyl, ₍ C1 _- C8) alkoxy, (C1 _- C8) haloalkoxy, _{( C2 -} C8) alkoxy, (C2 _- C8) alkoxy, (C2-C8) C ₂ -C ₈ ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) Alkyl, S (O) _n- (C ₁ -C ₈ ) Haloalkyl, OSO _2- (C ₁ -C ₈ ) Alkoxy, OSO _2- (C ₁ -C ₈ ) haloalkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) haloalkyl, C (O)-( C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkoxy, C (O) O- (C ₂ -C) ₈ ) Alkoxy, (C ₁ -C ₈ ) Alkoxy-O- (C ₁ -C ₈ ) Alkoxy, (C ₁ -C ₈ ) Alkoxy-S (O) _n- (C ₁ -C ₈ ) Alkoxy, C ( O)-(C ₁ -C ₈ ) Alkoxy-C (O) O- (C ₁ -C ₈ ) Substituent with one or more substituents independently selected from the group consisting of alkyl, phenyl and phenoxy. May;
(D) L is selected from ( ₁ ) saturated or unsaturated, substituted linear (C1- _C4 ) hydrocarbyl linkers and (2) saturated or unsaturated, substituted cyclic ₍ C3 _- C8) hydrocarbyl group linkers. Linker
Here, each of the linkers ligates Ar ² to ^NY , and where the substituted linear (C ₁ -C ₄ ) hydrocarbyl linker and the substituted cyclic (C ₃ -C ₈ ) hydrocarbyl linker are R ⁸ ,. It has one or more substituents independently selected from R ⁹ , R ¹⁰ , R ¹¹ and R ¹² , where each R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and ^{R 12} are -NR AC ( O) ^-RB , -NR AC ( ^O ) O ^- RB, -C (O) -OH or -C (O) O ^- RB selected from
Where ^RA is H or (C ₁ -C ₈ ) alkyl and RB is ( ^C ₁ -C ₈ ) alkyl or (C ₁ -C ₈ ) alkyl substituted with at least one phenyl. ;
(E) R ¹ is H, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n -(C ₁ -C ₈ ) alkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-OC (O)-(C ₁ -C ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-S (O) _n- (C ₁ -C ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-OC (O) O- (C ₁ -C ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-C (O) O- (C ₁ -C ₈ ) Alkyl, C (O) Alkyl, (C ₁ -C ₈ ) Alkyl-C (O)-(C ₁ -C ₈ ) ) Alkyl, (C ₁ -C ₈ ) alkyl phenyl, (C ₁ -C ₈ ) alkyl-O-phenyl selected from the group.
Here, each alkyl, cycloalkyl, alkenyl and alkynyl are optionally H, F, Cl, Br, I, CN, NO ₂ , oxo, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C3 _- C8) cycloalkyl, (C1 _- C8) alkoxy, ₍ C1 _- C8) haloalkoxy, _{( C2 -} C8) alkenyl, ₍ C2 _- C8) alkynyl, S ₍ O) ) _N- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) halo alkyl , C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C) ₈ ) Alkyl, C (O)-(C1 _- C8) haloalkyl, C ₍ O) O- (C1 _- C8) haloalkyl, C ₍ O)-(C3 _- C8) cycloalkyl, C ₍ O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) Alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl -C (O) O- (C ₁ -C ₈ ) may be substituted with one or more substituents independently selected from the group consisting of alkyl, phenyl and phenoxy;
(F) Q and Q ¹ are independently selected from the group consisting of O and S;
(G) R ² is (J), H, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, C (O)-(C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C) ₁ -C ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne phenyl, (C ₁ -C ₈ ) Alkyne-O-Phenyl, C (O)-(Het-1), (Het-1), (C ₁ ) -C ₈ ) Alkyne- (Het _{- 1} ), (C1-C ₈ ) Alkyne-OC (O)-(C1-C ₈ ) Alkyne, (C1 _- C ₈ ) Alkyne-OC (O) O- (C ₁ -C ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne-OC (O) -NR ^x R ^y , (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ ) -C ₈ ) Alkyne- (Het- ₁ ), (C1-C ₈ ) Alkyne-C (O)-(Het- ₁ ), (C1-C ₈ ) Alkyne-C (O) -N (R ^x ) ) (C ₁ -C ₈ ) Alkyne (NR ^x R ^y ) -C (O) OH, (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne- NR ^x R ^y , (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne-N (R ^x ) -C (O) O- (C ₁ -C) ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne (N (R ^x ) -C (O) O- (C ₁ -C ₈ ) ) Alkyl) -C (O) OH, (C ₁ -C ₈ ) Alkyl-C (O)-(Het-1) -C (O) O- (C ₁ -C ₈ ) Alkyne, (C ₁ -C 8) ₈ ) Alkyne-OC (O) O- (C1 _- C8) alkyl, ₍ C1 _- C8) alkyl _- OC (O)- ₍ C1 _- C8) alkyl, ₍ C1 _- C8) alkyl -OC (O)-(C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkyl-OC (O)-(Het-1), (C ₁ -C ₈ ) alkyl-OC (O)- (C ₁ -C ₈ ) Alkyne-N (R ^x ) -C (O) O- (C ₁ -C ₈ ) Alkyne, (C _1- Group consisting of C ₈ ) alkyl-NR ^x R ^y , (C1 _- C ₈ ) alkyl-S (O) _n- (Het- ₁ ) and (C1-C ₈ ) alkyl-O- (Het-1) Selected from
Here, each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and (Het-1) are optionally H, F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ -C ₈ ). Alkyl, (C1 _- C8) haloalkyl, ₍ C3 _- C8) cycloalkyl, (C1 _- C8) alkoxy, _{( C2 -} C8) alkenyl, ₍ C2 _- C8) alkynyl, S ₍ O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) Haloalkyl, C (O) H, C (O) OH, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) Alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) Alkyl, C (O) O- (C1 _- C8) alkyl, C ₍ O)-(C1 _- C8) haloalkyl, C ₍ O) O- (C1 _- C8) haloalkyl, C ₍ O) -(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ ) -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl, phenoxy, Si ((C ₁ -C ₈ ) alkyl) ₃ , S (O) It may be substituted with one or more substituents independently selected from the group consisting of _n -NR ^x R ^y and (Het-1);
(H) R ³ is (C ₃ -C ₈ ) cycloalkyl, phenyl, (C ₁ -C ₈ ) alkyl phenyl, (C ₁ -C ₈ ) alkyl-O-phenyl, (C ₂ -C ₈ ) alkenyl- Selected from the group consisting of O-phenyl, (Het- ₁ ), (C1 _- C8) alkyl- (Het- ₁ ) and (C1 _- C8) alkyl-O- (Het-1).
Here, each alkyl, cycloalkyl, alkenyl, phenyl and (Het-1) are optionally H, F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) halo alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ ) -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO ₂ -(C ₁ -C ₈ ) haloalkyl, C (O) H, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) Alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) halo alkyl, C ( O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₁ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- ( C ₂ -C ₈ ) alkenyl, O- (C ₁ -C ₈ ) alkyl, S- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, One or more independently selected from the group consisting of C (O)-(C ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl, phenoxy and (Het-1). May be substituted with a substituent of;
(I) R ⁴ is (J), H, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, C (O)-(C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C) ₁ -C ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne phenyl, (C ₁ -C ₈ ) Alkyne-O-Phenyl, C (O)-(Het-1), (Het-1), (C ₁ ) -C ₈ ) Alkyne- (Het _{- 1} ), (C1-C ₈ ) Alkyne-OC (O)-(C1-C ₈ ) Alkyne, (C1 _- C ₈ ) Alkyne-OC (O) O- (C ₁ -C ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne-OC (O) -NR ^x R ^y , (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ ) -C ₈ ) Alkyne- (Het- ₁ ), (C1-C ₈ ) Alkyne-C (O)-(Het- ₁ ), (C1-C ₈ ) Alkyne-C (O) -N (R ^x ) ) (C ₁ -C ₈ ) Alkyne (NR ^x R ^y ) -C (O) OH, (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne- NR ^x R ^y , (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne-N (R ^x ) -C (O) O- (C ₁ -C) ₈ ) Alkyne, (C ₁ -C ₈ ) Alkyne-C (O) -N (R ^x ) (C ₁ -C ₈ ) Alkyne (N (R ^x ) -C (O) O- (C ₁ -C ₈ ) ) Alkyl) -C (O) OH, (C ₁ -C ₈ ) Alkyl-C (O)-(Het-1) -C (O) O- (C ₁ -C ₈ ) Alkyne, (C ₁ -C 8) ₈ ) Alkyne-OC (O) O- (C1 _- C8) alkyl, ₍ C1 _- C8) alkyl _- OC (O)- ₍ C1 _- C8) alkyl, ₍ C1 _- C8) alkyl -OC (O)-(C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkyl-OC (O)-(Het-1), (C ₁ -C ₈ ) alkyl-OC (O)- (C ₁ -C ₈ ) Alkyne-N (R ^x ) -C (O) O- (C ₁ -C ₈ ) Alkyne, (C _1- Group consisting of C ₈ ) alkyl-NR ^x R ^y , (C1 _- C ₈ ) alkyl-S (O) _n- (Het- ₁ ) and (C1-C ₈ ) alkyl-O- (Het-1) Selected from
Here, each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and (Het-1) are optionally H, F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ -C ₈ ). Alkyl, (C1 _- C8) haloalkyl, ₍ C3 _- C8) cycloalkyl, (C1 _- C8) alkoxy, _{( C2 -} C8) alkenyl, ₍ C2 _- C8) alkynyl, S ₍ O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) Haloalkyl, C (O) H, C (O) OH, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) Alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) Alkyl, C (O) O- (C1 _- C8) alkyl, C ₍ O)-(C1 _- C8) haloalkyl, C ₍ O) O- (C1 _- C8) haloalkyl, C ₍ O) -(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ ) -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- (C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl, phenoxy, Si ((C ₁ -C ₈ ) alkyl) ₃ , S (O) It may be substituted with one or more substituents independently selected from the group consisting of _n -NR ^x R ^y and (Het-1);
(J) R ² and R ⁴ may be combined with C ^X (Q ¹ ) ( ^NX ) to form 4- to 7-membered saturated or unsaturated heterocyclic rings, which are further nitrogen, It may contain one or more heteroatoms selected from the group consisting of sulfur and oxygen, where each heterocyclic ring is optionally independently selected from the group consisting of R ⁵ , R ⁶ and R ⁷ . It may be substituted with one or more substituents,
Here, R ⁵ , R ⁶ and R ⁷ are independently H, F, Cl, Br, I, CN, OH, NO ₂ , NR ^x R ^y , oxo, tioxo, (C ₁ -C ₈ ) alkyl, respectively. (C ₁ -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) halo alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ ) -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO ₂ -(C ₁ -C ₈ ) haloalkyl, C (O) H, C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)- (C1 _- C8) haloalkyl, C ₍ O) O- (C1 _- C8) haloalkyl, C ₍ O)-(C3 _- C8) cycloalkyl, C ₍ O) O- (C3 _- C) ₈ ) Cycloalkyl, C (O)- ₍ C2 _- C8) alkenyl, C (O) O- ₍ C2 _- C8) alkenyl, (C1 _- C8) Alkyl _- O- (C1 _- C) ₈ ) Alkyl, (C ₁ -C ₈ ) Alkyl-S (O) _n- (C ₁ -C ₈ ) Alkyl, C (O)-(C ₁ -C ₈ ) Alkyl-C (O) O- (
C1 _- C ₈ ) Selected from the group consisting of alkyl, phenyl and (Het-1);
(K) R ^x and R ^y are independently H, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₂ -C ₈ ). Alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) alkyl, C (O) H, C (O)-( C1 _- C8) alkyl, C ₍ O) O- (C1 _- C8) alkyl, C ₍ O)-(C3 _- C8) cycloalkyl, C ₍ O) O- ₍ C3 _- C8) ) Cycloalkyl, C (O)- ₍ C2 _- C8) alkenyl, C (O) O- (C2 _- C8) alkenyl, ₍ C1 _- C8) alkyl _- O- ₍ C1 _- C8) ) Alkyl, (C ₁ -C ₈ ) Alkyl-S (O) _n- (C ₁ -C ₈ ) Alkyl, C (O)-(C ₁ -C ₈ ) Alkyl-C (O) O- (C ₁ ) Selected from the group consisting of -C ₈ ) alkyl, phenyl and (C ₁ -C ₈ ) alkyl phenyl.
Here, each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl and alkylphenyl are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ) alkyl, (C _1- ). C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) halo alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) Alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ ) -C ₈ ) haloalkyl, C (O) H, C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C ₈ ) alkyl, C (O)-(C _1- ) C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) haloalkyl, C (O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl , C (O)- ₍ C2 _- C8) alkenyl, C (O) O- (C2 _- C8) alkenyl, ₍ C1 _- C8) alkyl _- O- ₍ C1 _- C8) alkyl, (C ₁ -C ₈ ) Alkyne-S (O) _n- (C ₁ -C ₈ ) Alkyne, C (O)-(C ₁ -C ₈ ) Alkyne-C (O) O- (C ₁ -C ₈ ) ) May be substituted with one or more substituents independently selected from the group consisting of alkyl, phenyl and (Het-1);
(L) (Het-1) is a 5- or 6-membered saturated or unsaturated heterocyclic ring containing one or more heteroatoms independently selected from nitrogen, sulfur or oxygen.
Here, the heterocyclic ring is optionally H, F, Cl, Br, I, CN, NO ₂ , oxo, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ ). -C ₈ ) alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, S (O) _n- (C ₁ -C ₈ ) alkyl, OSO _2- (C ₁ -C ₈ ) alkyl , C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O- (C ₁ -C) ₈ ) Alkyl, C (O)-(C ₃ -C ₈ ) cycloalkyl, C (O) O- (C ₃ -C ₈ ) cycloalkyl, C (O)-(C ₂ -C ₈ ) alkenyl, C (O) O- (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkyl-O- (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkyl-S (O) _n- ( Independently selected from the group consisting of C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl and phenoxy 1 May be substituted with more than one substituent,
Here, each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl and phenoxy substituents are optionally H, F, Cl, Br, I, CN, NO ₂ , (C ₁ -C ₈ ) alkyl, (C ₁ ). -C ₈ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) haloalkoxy, (C ₂ -C ₈ ) alkoxy, (C ₂ -C ₈ ) ) Alkinyl, S (O) _n- (C ₁ -C ₈ ) alkyl, S (O) _n- (C ₁ -C ₈ ) haloalkyl, OSO _2- (C ₁ -C ₈ ) alkyl, OSO _2- (C) ₁ -C ₈ ) haloalkyl, C (O) -NR ^x R ^y , (C ₁ -C ₈ ) alkyl-NR ^x R ^y , C (O)-(C ₁ -C ₈ ) alkyl, C (O) O -(C ₁ -C ₈ ) alkyl, C (O)-(C ₁ -C ₈ ) haloalkyl, C (O) O- (C ₁ -C ₈ ) haloalkyl, C (O)-(C ₃ -C ₈ ) ) Cycloalkyl, C ₍ O) O- ₍ C3 _- C8) cycloalkyl, C ₍ O)-( _{C2 -} C8) alkoxy, C (O) O- (C2-C8) alkoxy, ( C1 _- C8) Alkoxy-O- (C1 _- C8) Alkoxy, ₍ C1 _- C8) Alkoxy-S ₍ O) _n- (C1 _- C8) Alkoxy, _{C (} O)-(C) It may be substituted with one or more substituents independently selected from the group consisting of ₁ -C ₈ ) alkyl-C (O) O- (C ₁ -C ₈ ) alkyl, phenyl and phenoxy;
(M) n is 0, 1 or 2 individually]
Molecules with, as well as N-oxides, agriculturally acceptable acid addition salts , solvates , isotopes , split steric isomers or tautomers. The following equation ("Equation 1 " or "Equation 2")

[During the ceremony:
(A) Ar ¹ is a substituted phenyl, wherein the substituted phenyl is (C ₁ -C ₆ ) alkyl, (C ₁ -C ₆ ) haloalkyl, (C ₁ -C ₆ ) alkoxy and (C ₁ -C ₆ ). ) Has one or more substituents selected independently of haloalkoxy;
(B) Het is triazolyl;
(C) Ar ² is phenyl or substituted phenyl, where the substituted phenyls are F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ − C ₆ ) alkyl and (C ₁ −. C ₆ ) Has one or more substituents independently selected from haloalkyl;
(D) R ¹ is H, (C ₁ -C ₆ ) alkyl or (C ₂ -C ₆ ) alkoxy, where the alkyl is optionally (C ₃ -C ₆ ) cycloalkyl or (C _1- ). C ₆ ) Alkoxy substituted;
(E) Q and Q ¹ are independently selected from the group consisting of O and S;
(F) R ² is (J), H or (C ₁ -C ₆ ) alkyl;
(G) R ³ is phenyl, where the phenyl is optionally F, Cl, Br, I, CN, NO ₂ , NR ^x R ^y , (C ₁ -C ₆ ) alkyl, (C ₁ -C). ₆ ) Substituted with one or more substituents independently selected from haloalkyl, phenyl, (C1 _- C ₆ ) alkoxy and (C1 _- C ₆ ) haloalkoxy;
(H) R ⁴ is (J), H or (C1 _- C ₆ ) alkyl;
(J) R ² and R ⁴ may be 1- to 4-member saturated or unsaturated hydrocarbyl links, which may contain one or more heteroatoms selected from nitrogen, sulfur and oxygen, C ^x Together with (Q ¹ ) (N ^x ), it forms a cyclic structure, where the hydroxycarbyl link is optionally one or more substituents independently selected from R ⁵ , R ⁶ and R ⁷ . May be substituted, where each R ⁵ , R ⁶ and R ⁷ are H, F, Cl, Br, I, CN, OH, NO ₂ , NR ^x R ^y , (C ₁ -C ₆ ) alkyl , (C ₁ -C ₆ ) haloalkyl, (C ₁ -C ₆ ) alkoxy, (C ₁ -C ₆ ) haloalkoxy, phenyl and oxo;
(K) R ^x and R ^y are independently H, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₂ -C ₆ Selected from alkenyl, C ₂ -C ₆ alkynyl and phenyl; and (L) L is (1) saturated or unsaturated, substituted linear (C ₁ -C ₄ ) hydrocarbyl linker and (2) saturated or unsaturated, It is a linker selected from the substituted cyclic (C ₃ -C ₈ ) hydrocarbyl group linkers.
Here each of the linkers has Ar ² linked to ^NY , where the substituted linear (C ₁ -C ₄ ) hydrocarbyl linker and the substituted ring (C ₃ -C ₈ ) hydrocarbyl linker are R. It has one or more substituents independently selected from ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² , where each R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² are -NR ^A. Selected from ^C (O) ^-RB , -NR ^A C (O) O ^- RB, -C (O) -OH or -C (O) O-RB,
Where ^RA is H or (C ₁ -C ₈ ) alkyl and RB is ( ^C ₁ -C ₈ ) alkyl or (C ₁ -C ₈ ) alkyl substituted with at least one phenyl].
Molecules and their tautomers. The molecule is the following formula

The molecule according to claim 1 or 2, which is a tautomer having. A method comprising applying the molecule of claim 1 or 2 to a place of control of a pest in an amount sufficient to control such a pest. Molecules having a structure from the compounds listed in Table 1.

A method comprising applying the molecule of claim 5 to a place of control of pests in an amount sufficient to control such pests. Molecules having a structure from the compounds listed in Table 2.

A method comprising applying the molecule of claim 7 to a place of control of pests in an amount sufficient to control such pests. The method according to claim 4, 6 or 8, wherein the pest is Beet armyworm (BAW), cabbage looper (CL) or Aedes aegypti (YFM). The molecule of claim 1, wherein at least one H is ² H or at least one C is ¹⁴ C. A composition comprising the molecule according to claim 1 and at least one other compound having insecticidal, herbicidal, acaricidal, nematode or bactericidal / fungicidal activity. A composition comprising the molecule and seed according to claim 1. A method comprising applying the molecule of claim 1 to a genetically modified plant or genetically modified seed that has been genetically modified to express one or more particular traits. A method comprising oral administration or topical application of the molecule of claim 1 to a non-human animal for suppression of endoparasites, ectoparasites or both.