Novel Compound for Crop Protection

Abstract

The present invention provides a compound represented by the following chemical formula I and a pest control composition comprising the same. [Chemical Formula I]

Description

Technology Field

[0001] The present invention relates to a novel compound for crop protection agents. Background Technology

[0002] Plant parasitic nematodes, which penetrate plants and steal nutrients, are known to be harmful pathogens to crops. It has been reported that approximately 14% of global crop damage is caused by nematode infections. In particular, the situation is extremely serious in banana production, where damage caused by nematode infections exceeds 65%.

[0003] Meanwhile, one example of a plant-parasitic nematode that damages crops is the root-knot nematode. Root-knot nematodes have a wide host range, infecting approximately 2,000 species of plants, and survive by parasitizing plant roots and extracting nutrients from the plant body. In particular, as greenhouse cultivation sites, where root-knot nematodes thrive, are widely used, the population of these nematodes is increasing rapidly.

[0004] For this reason, attempts are being made to eliminate various types of nematodes using diverse control agents; however, effective eradication remains difficult due to the widespread development of resistance in the nematodes. Consequently, the use of more toxic and high-concentration control agents is being considered, but this can cause secondary harm to humans or animals consuming crops due to agent residues remaining on the crops.

[0005] Therefore, there is a need for novel nematicides that can provide excellent control efficacy against nematodes at relatively low concentrations while being safer for humans and livestock. The problem to be solved

[0006] The present invention aims to provide a novel compound capable of effectively killing plant parasitic nematodes and a control composition containing the same.

[0007] The compound according to the present invention can exhibit an excellent mortality rate against plant parasitic nematodes, such as root-knot nematodes, even at relatively low concentrations. means of solving the problem

[0008] In one embodiment, the present invention provides a compound represented by the following chemical formula I:

[0009] [Chemical Formula I]

[0010]

[0011] In the above formula,

[0012] Het is a 5 to 8-membered heterocycle comprising at least one heteroatom among N, O, S, and P as a constituent element, and

[0013] Z is O or S, and

[0014] n1 is an integer from 0 to 4, and when n1 is plural, R 1 They are identical or different from each other,

[0015] R 1 Each independently, halogen, cyano, nitro, SF5, OCN, SCN, Si(R 15 )3, OR 4 , NR 5 R 6 , C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O)2R9 , OS(O)2NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O)2R 9 or N(R 10 )S(O)2NR 11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or each halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 It is an aryl or pentagonal or hexacyclic heterocycle;

[0016] R 2 is hydrogen, halogen, cyano, nitro, SF5, OCN, SCN, Si(R 15)3, OR 4 , NR 5 R 6 , C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O)2R 9 , OS(O)2NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O)2R 9 or N(R 10 )S(O)2NR 11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or each halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 It is an aryl or pentagonal or hexacyclic heterocycle;

[0017] R 3 Silver is hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O)2NR 11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl C 3-20 Cycloalkenyl; C 1-6 Alkoxy or halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 Aril is;

[0018] Q are halogen, cyano, nitro, SF5, OCN, SCN, Si(R), respectively. 15 )3, OR 4 , NR 5 R 6 , C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O)2R 9 , OS(O)2NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O)2R 9 , N(R 10 )S(O)2NR 11 R12 and R 14 C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 It is an aryl, 5-membered or 30-membered heterocycle;

[0019] X is independently O or S;

[0020] R 4 Each independently hydrogen, halogen, and C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0021] R 4a are independently hydrogen, C 1-6 alkyl or C 1-6 It is a haloalkyl;

[0022] R 5 are independently hydrogen, NR 5a R 6a , C 1-6 Alkyl, C1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O)2NR 11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0023] R 5a Each independently hydrogen or C 1-6 It is alkyl;

[0024] R6 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 It is a cycloalkenyl;

[0025] R 6a are independently hydrogen, C 1-6 Alkyl, C(O)R 13 or C(O)OR 13 is;

[0026] R 7 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a, C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0027] R 7a C each independently 1-6 alkyl or C 1-6 It is a haloalkyl;

[0028] R 8 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O)m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0029] R 8a C each independently 1-6 alkyl or C 1-6 It is a haloalkyl;

[0030] R 9 are independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0031] R 9a C each independently 1-6 alkyl or C 1-6 It is a haloalkyl;

[0032] R 10 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , S(O) m R 9a or S(O)2NR 11 R 12 And;

[0033] R 10a are independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 It is a haloalkinyl;

[0034] R 11 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11a R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11a R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10a )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0035] R 11a are independently hydrogen, C 1-6 Alkyl, C 2-6 Alkenyl or C 2-6 It is alkynyl;

[0036] R 12 are independently hydrogen, NR 5a R 6a , C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O)2NR11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0037] R 13 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9aC that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 It is a cycloalkenyl;

[0038] R 14 Each independently halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or each halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 It is an aryl or pentagonal or hexacyclic heterocycle;

[0039] R 15 are independently, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 Aril is;

[0040] m is independently 0, 1, or 2.

[0041] In one embodiment, the present invention provides an acceptable salt of the compound, its enantiomer, its diastereomer, its geometric isomer, its solvate, or its tautomer.

[0042] In one embodiment, the present invention provides a pest control composition comprising at least one of its acceptable salt, its enantiomer, its diastereomer, its solvate, its geometric isomer, and its tautomer as an active substance.

[0043] This control composition has a mortality rate of 40% or more, specifically 50% or more, and even more specifically 70% or more, measured against nematodes when the concentration of the active substance is 50 ppm. In other words, the present invention provides a control composition that exhibits a mortality effect against nematodes despite containing the active substance at a relatively low concentration of 50 ppm. Effects of the invention

[0044] The compound according to the present invention is capable of effective killing action against plant parasitic nematodes, such as root-knot nematodes.

[0045] The pest control composition according to the present invention containing the above compound exhibits an excellent mortality rate even at relatively low concentrations. Brief explanation of the drawing

[0046] Figure 1 is an NMR graph of the compound of Example 1. Figure 2 is an NMR graph of the compound of Example 2. Figure 3 is an NMR graph of the compound of Example 3. Figure 4 is an NMR graph of the compound of Example 4. Figure 5 is an NMR graph of the compound of Example 5. Figure 6 is an NMR graph of the compound of Example 6. Figure 7 is an NMR graph of the compound of Example 7. Figure 8 is an NMR graph of the compound of Example 8. Figure 9 is an NMR graph of the compound of Example 9. Figure 10 is an NMR graph of the compound of Example 10. Figure 11 is an NMR graph of the compound of Example 11. Figure 12 is an NMR graph of the compound of Example 12. Figure 13 is an NMR graph of the compound of Example 13. Figure 14 is an NMR graph of the compound of Example 14. Figure 15 is an NMR graph of the compound of Example 15. Figure 16 is an NMR graph of the compound of Example 16. Figure 17 is an NMR graph of the compound of Example 17. Specific details for implementing the invention

[0047] In the following, the intent, operation, and effects of the present invention will be described in more detail through the salsa mode of the present invention and specific embodiments thereof. However, the following embodiments are presented as examples to aid in understanding the present invention, and the scope of the invention is not limited to these examples.

[0048] Embodiments of the invention will be described in more detail in the order of "compound" and "control composition" according to the present invention.

[0049] Prior to this, terms and words used in this specification and claims should not be interpreted as being limited to their ordinary or dictionary meanings, but should be interpreted in a meaning and concept consistent with the technical spirit of the invention, based on the principle that the inventor can appropriately define the concept of the terms to best describe his invention.

[0050] Therefore, it should be understood that the configuration of the embodiments described in this specification is merely one of the most preferred embodiments of the present invention and does not represent all of the technical ideas of the present invention, and that various equivalents and modifications that can replace them may exist at the time of filing this application.

[0051] In this specification, singular expressions include plural expressions unless the context clearly indicates otherwise.

[0052] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components. Thus, for example, a composition comprising compound A may include other compounds in addition to A. However, the term "comprising" also encompasses, in a more restrictive sense as a specific embodiment thereof, "essentially / essentially composed of" and "composed of," so that, for example, a "composition comprising compound A" may also be (essentially / essentially) composed of compound A.

[0053] In connection with this, in this specification, terms such as “comprising” or “having” are intended to specify the existence of the implemented features, numbers, steps, components, or combinations thereof, and should be understood as not precluding the existence or addition of one or more other features, numbers, steps, components, or combinations thereof.

[0054] In this specification, enantiomers refer to two stereoisomers of a compound that are mirror images of each other but cannot be superimposed.

[0055] In this specification, diastereomers refer to stereoisomers that have two or more chiral centers and whose molecules are not mirror images of each other. Diastereomers have different physical properties, such as melting point, boiling point, spectral properties, and reactivity. A mixture of diastereomers can be separated under high-resolution analytical procedures such as electrophoresis and chromatography.

[0056] In this specification, geometric isomers refer to the cis type, in which atoms or groups of atoms of the same type are on the same side around the double bond, the trans type, in which atoms or groups of atoms of the same type are on opposite sides around the double bond, or the E type or Z type according to the CIP priority.

[0057] In this specification, tautomers or tautomer forms refer to geometric isomers of different energies that are compatible through a low energy barrier. For example, proton tautomers (also known as protic tautomers) involve interconversion through the transfer of protons, e.g., keto-enol and imine-enamine isomerization. Valence tautomers involve interconversion by the retransfer of some bonding electrons.

[0058] In this specification, a solvate refers to an aggregate or complex of one or more solvent molecules and a compound of the present invention. Examples of solvents forming a solvate include, but are not limited to, water, isopropanol, ethanol, methanol, dimethyl sulfoxide, ethyl acetate, acetic acid, and ethanolamine. A hydrate refers to a complex in which the solvent molecule is water.

[0059] In this specification, the term "acceptable salt" refers to a salt of an active compound prepared with an acid or a base, depending on a specific substituent based on the compound described herein. If the compound according to the invention contains a relatively acidic functional group, a base addition salt can be obtained by contacting such a neutral compound with a sufficient amount of the desired base in a solvent-free or suitable inert solvent.

[0060] Acceptable salts include, for example, alkali metal salts, for example, sodium or potassium salts; alkaline earth metal salts, for example, calcium or magnesium salts; ammonium salts; aliphatic amine salts, for example, trimethylamine, triethylamine, dicyclohexylamine, ethanolamine, diethanolamine, triethanolamine or procaine salts; aralkyl amine salts, for example, N,N-dibenzylethylenediamine salts; heterocyclic aromatic amine salts, for example, pyridine salt, picolino salt, quinoline salt or isoquinoline salt; quaternary ammonium salts, for example, tetramethylammonium salt, tetraethylammonium salt, benzyltrimethylammonium salt, benzyltriethylammonium salt, benzyltributylammonium salt, methyltrioctylammonium salt or tetrabutylammonium salt; and basic amino acid salts, for example, arginine salt or lysine salt. Acid salts are, for example, inorganic acid salts, for example, hydrochloride, sulfate salt, nitrate salt, phosphate salt, carbonate salt, hydrogen carbonate or perchlorate; organic acid salts, for example, acetate, propionate, lactate, malate, fumarate, tartaric acid salt, malate, fumarate, citrate salt, ascorbate, formic acid; sulfonates, for example, methanesulfonate, isothionate, benzenesulfonate or p-toluenesulfonate; and acidic amino acid salts, for example, aspartate or glutamate. Solvents of the compounds of the present invention include, but are not limited to, alcoholates and hydrates.

[0061] In this specification, where a quantity, concentration, or other value or parameter is given as an enumeration of a range, a preferred range, a preferred upper limit, and a preferred lower limit, it should be understood that any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether the range is disclosed separately, specifically discloses all ranges that may be formed. Where a range of numerical values ​​is mentioned in this specification, unless otherwise described, for example, without limiting terms such as greater than or less than, the range is intended to include its endpoint value and all integers and fractions within that range. The scope of the invention is not intended to be limited to the specific value mentioned when defining the range.

[0062] In this specification, the terms "nematode" or "control of nematodes" mean killing nematodes or preventing or hindering the occurrence, growth, and reproduction of nematodes.

[0063] In this specification, the terms “nematode” and “nematode group” refer to living organisms of the phylum Nematoda. As is commonly defined, “parasite” survives by living or growing within or metabolizing another organism described as a “host” (e.g., plants, humans, or animals). Examples of such nematodes include root-knot nematodes (Meloidogyne spp.), cyst nematodes (Globodera spp.), seed nematodes (Anguina spp.), stem-bulb nematodes (Ditylenchus spp.), stem nematodes (Ditylenchus spp.), root-rotting nematodes (Pratylenchus spp.), leaf nematodes (Aphelenchoides spp.), and citrus nematodes (Rotylenchulus spp.), depending on their morphology, mode of damage, and host.

[0064] The compound according to the present invention can exhibit activity against all species of nematodes, examples of which include Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi, Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, and Meloidogyne arenaria tamesi. Examples include, but are not limited to, arenariathamesi), Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyne exigua, Meloidogyne graminicola, Meloidogyne graminis, and Meloidogyne hapla.

[0065] In this specification, the term "substitution" may mean that a hydrogen atom bonded to a compound or any substituent (e.g., alkyl, etc.) is replaced by any substituent. The substitution site is not limited to the site where the hydrogen atom bonded to the compound or substituent exists, that is, any site where the hydrogen atom can be replaced by a substituent. If two or more substitutions occur, the two or more substituents may be identical or different from each other. Conversely, "non-substitution" may mean that no hydrogen atom bonded to a carbon atom is replaced by any substituent.

[0066] Substituents applicable to the above "substitution" may be appropriately selected from the following groups of substituents without restriction, but this is for illustrative purposes only and the category of substitutable substituents is not limited to these substituents.

[0067] - Substituent group: Substituent or non-substituent C 1-10 Alkyl groups, substituted or unsubstituted C 2-10 Alkenyl group, substituted or non-substituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-30 Aryl group, substituted or unsubstituted 3 to 30-membered heterocyclic group, substituted or unsubstituted C 1-10 Alkoxy group, substituted or non-substituted C 3-30 Alkylsilyl group, substituted or unsubstituted C 1-10 Haloalkyl groups, substituted or unsubstituted C 1-10 Haloalkoxy group, substituted or non-substituted C 1-10 haloalkylthio groups, substituted or unsubstituted C 2-10 Alkenyloxy group, substituted or unsubstituted C 3-10 Cycloalkyloxy group, substituted or unsubstituted C 6-30 Aryloxy group, substituted or unsubstituted 3 to 30-membered heterocyclooxy group, substituted or unsubstituted C 3-30 Alkylsilyloxy group, substituted or unsubstituted C 1-10 Alkyl carbonyl group, substituted or unsubstituted C2-10 Alkenyl carbonyl group, substituted or unsubstituted C 3-10 Cycloalkyl carbonyl group, substituted or unsubstituted C 6-30 Aryl carbonyl group, substituted or unsubstituted 3 to 30-membered heterocyclic carbonyl group, substituted or unsubstituted C 1-10 Alkylthio groups, substituted or unsubstituted C 2-10 Alkenylthio group, substituted or non-substituted C 3-10 Cycloalkylthio groups, substituted or unsubstituted C 6-30 Arylthio group, substituted or unsubstituted 3 to 30-membered heterocyclothio group, aldehyde group, carboxyl group, ester group, halogen group, substituted or unsubstituted oxime group, substituted or unsubstituted carbamate group, carbonate group, hydroxyl group, substituted or unsubstituted amino group, imine group, cyano group, nitro group, amide group, thiol group, sulfone group, and phosphate group. Provided, among the substituents listed above, C 1-10 Alkyl residues are -O-, -S-, -SO-, -SO 2- , -NR a- (R a is hydrogen or substituted or unsubstituted C 1-10 Alkyl), -N=, =N-, -POR a- and -PO4R a- It may be interposed by a heteroatom group selected from, and the heterocycle residue includes at least one of sulfur, nitrogen, phosphorus, and oxygen as a ring constituent atom.

[0068] A substituent more preferably applicable to the above "substitution" is, in detail, a halogen group, C 1-10 Alkyl group, C 2-10 Alkenyl group, C 2-10 alkynyl group, C 3-10 Carbocycle group, C 3-10 Cycloalkyl group, C 6-30 Aryl group, 3 to 30-membered heterocyclic group, C 1-10 Alkoxy group, C 2-10 Alkenyloxy group, C 2-10alkynoyloxy group, C 3-10 Cycloalkyloxy group, C 6-30 Aryloxy group, 3 to 30 heterocyclic oxy group, C 1-10 Alkyl carbonyl group, C 2-10 alkenyl carbonyl group, C 1-10 Alkyl carboxyl group, C 2-10 alkenylcarboxylic group, C 3-10 Cycloalkylcarbonyl group, C 6-30 Aryl carbonyl group, 3 to 30 heterocyclic carbonyl group, C 1-10 Alkylthio group, C 2-10 alkenylthio group, C 3-10 Cycloalkylthio group, C 6-30 It can be selected from the group consisting of an arylthio group, a 3 to 30 heterocyclic thio group, an aldehyde group, a carboxyl group, a hydroxyl group, an amino group, an imine group, a cyano group, a nitro group, an amide group, a thiol group, a sulfone group, and a phosphate group.

[0069] If a substituent is not separately described or mentioned in the chemical formulas described in this specification, it may be considered that hydrogen is bonded, and in some cases, a substituent may be absent depending on the ring constituent elements forming the heterocycle.

[0070] Any substituents described herein, e.g., alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, cycloalkyl, aryl, may have a hydrogen among them substituted with any one of the substituents selected from the group of substituents, or conversely, may not be substituted. Accordingly, unless otherwise specified in this specification, substituents are intended to include unsubstituted substituents and forms in which the hydrogen of a substituent is substituted with any substituent.

[0071] In this specification, the term “group” as described means that it is combined with a preceding substituent, for example, alkyl, to form the term “alkyl group,” and that the alkyl can be bonded to any position of the compound or substituent, or is bonded.

[0072] In this specification, means a site that is bonded to another substituent or bonding site.

[0073] In this specification, halogens may include Cl, F, Br, and I.

[0074] In this specification, alkyl refers to the number of carbon atoms indicated (i.e., C) either itself or as part of another substituent, unless otherwise noted. 1-10 It means a straight-chain or branched-chain monovalent saturated aliphatic hydrocarbon having 1 to 10 carbons.

[0075] Examples of alkyls include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, Examples include 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but these are non-limiting examples and the scope of the invention is not limited to them.

[0076] In this specification, alkenyl refers to a monovalent unsaturated aliphatic hydrocarbon containing a double bond, and may be a straight chain or a branched chain. Alkenyls are, for example, ethenyl, 1-propenyl, 2-propenyl or 1-methylethenyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propphenyl, 1-ethyl-1-methyl-2-propphenyl, 1-ethyl-2-methyl-1-propphenyl,Examples include, but are not limited to, 1-ethyl-2-methyl-2-propenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl, 1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, and 5-decenyl.

[0077] In this specification, alkynyl refers to a monovalent unsaturated aliphatic hydrocarbon containing a triple bond, may be straight-chain or branched-chain, e.g., 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-fentinyl, 2-fentinyl, 3-fentinyl, 4-fentinyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexinyl, 2-hexinyl, 3-hexinyl, 4-hexinyl, 5-hexinyl, 1-methyl-2-fentinyl, 1-methyl-3-fentinyl, Examples include, but are not limited to, 1-methyl-4-fentinyl, 2-methyl-3-fentinyl, 2-methyl-4-fentinyl, 3-methyl-1-fentinyl, 3-methyl-4-fentinyl, 4-methyl-1-fentinyl, 4-methyl-2-fentinyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, and 2,5-hexadinyl.

[0078] In this specification, haloalkyl is synonymous with "alkyl halides" and "alkyls substituted with halogens," and may refer to an alkyl in which any hydrogen atom in the alkyl group is substituted with any halogen, for example, a halogen atom selected from Cl, F, Br, and I. For example, -CF3, -CH2Cl, -CH2CF3, -C(Cl2)CF3, etc. are haloalkyl groups, but the scope of the present invention is not limited to these.

[0079] In this specification, an alkoxy refers to a substituent in which oxygen is bonded to an alkyl group, and this may be a straight chain, a branched chain, or a cyclic chain. Examples of alkoxy groups specifically include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, or their monohalogenated and polyhalogenated variants, but the scope of the present invention is not limited to these.

[0080] In this specification, "amino" is intended to encompass monovalent primary amines, monovalent secondary amines, and monovalent tertiary amines. That is, an amino group refers to both a monovalent group in which two hydrogen atoms are bonded to a nitrogen atom and a monovalent group in which at least one hydrogen atom is substituted with another substituent. In the above, the group in which two hydrogen atoms are bonded to a nitrogen atom may be an unsubstituted amino group, and the group in which at least one hydrogen atom is substituted with another substituent may be a substituted amino group. Meanwhile, in an amino group comprising two substituents, each substituent may be the same or different from one another.

[0081] In this specification, “carbocycle” and “carbocyclic” mean a ring in which the ring constituent atoms are carbon. A carbocycle may be aliphatic or aromatic, saturated or unsaturated, and monocyclic or polycyclic. A polycyclic ring may be a fused, bridged, or spiro-polycyclic ring. A monocyclic carbocycle may have 3 to 17 carbon atoms, more specifically 3 to 14 carbon atoms, more specifically 3 to 10 carbon atoms, and particularly specifically 3 to 7 carbon atoms.

[0082] In this specification, cycloalkyl refers to a monovalent aliphatic carbocycle in which one hydrogen atom is missing from any position among the carbon atoms constituting the ring. Examples of cycloalkyls include, butyl cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexylene 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0083] In this specification, cycloalkenyl refers to a cyclic hydrocarbon that includes a double bond between carbon atoms constituting the ring and is a monovalent carbocycle with one hydrogen atom missing at any position. Examples of cycloalkenyls include, but are not limited to, cyclopropenyl, cyclobutenyl, and cyclopentenyl.

[0084] In this specification, aryl refers to a ring comprising a polyunsaturated, typically aromatic hydrocarbon ring, wherein the aryl may be monocyclic or polycyclic. In the case of polycyclic, it includes a form in which only an aromatic hydrocarbon ring is fused and a form in which an aliphatic hydrocarbon ring is fused together with an aromatic hydrocarbon. Examples of such aryls include monocyclic aryls such as phenyl groups, biphenyl groups, terphenyl groups, and quadrphenyl groups, and polycyclic aryls such as naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups, and benzopyrenyl groups.

[0085] In this specification, a heterocycle refers to a ring comprising 1 to 5 heteroatoms selected from non-carbon atoms, namely O, N, P, and S, as ring constituent atoms. The heterocycle may be aromatic, aliphatic, single-ring, or polycyclic, and non-limiting examples include thiophenyl groups, furanyl groups, pyrrolyl groups, imidazolyl groups, thiazolyl groups, oxazolyl groups, oxadiazolyl groups, pyridinyl groups, bipyridinyl groups, pyrimidinyl groups, triazolyl groups, pyridazolyl groups, pyrazinyl groups, pyridopyrimidyl groups, pyridopyrazinyl groups, pyrazinopyrazinyl groups, isooxazolyl groups, thiadiazolyl groups, etc., but the scope of the invention is not limited to these.

[0086] In this specification, heteroaryl refers to an aromatic heterocycle and may be a single ring or a polycyclic ring. A polycyclic ring includes not only a form in which a plurality of aromatic rings are fused, but also a form in which an aromatic ring and an aliphatic ring are fused. Examples of heteroaryls include pyridinyl groups, pyrrolyl groups, furanyl groups, thiophenyl groups, acridyl groups, quinolinyl groups, quinazolinyl groups, quinoxalinyl groups, phthalazinyl groups, isoquinolinyl groups, indolyl groups, carbazolyl groups, benzoxazolyl groups, benzimidazolyl groups, benzothiazolyl groups, benzocarbazolyl groups, benzothiophen groups, dibenzothiophen groups, benzofuranyl groups, phenanthrolinyl groups, phenothiazinyl groups, dibenzofuranyl groups, and fluorenyl groups, but the scope of the present invention is not limited to these.

[0087] In this specification, Oxy is "-OR oxy As a substituent that can be represented as ", where R oxy is, respectively, of substitution or non-substitution, C 1-10 Alkyl, C 2-10 Alkenyl, C 3-10 Carbocycle, C 3-10 Cycloalkyl, C 6-30 Aryl, 3 to 30-membered heterocycle, C 1-10 They may be haloalkyls, and the definitions of each of these are as previously explained.

[0088] In this specification, carbonyl is "-C(=O)R car As a substituent that can be represented as ", where R car is, respectively, of substitution or non-substitution, C 1-10 Alkyl, C 2-10 Alkenyl, substituted, or non-substituted C 3-10 Carbocycle, C 3-10 Cycloalkyl, C 6-30 Aryl, 3 to 30-membered heterocycle, C 1-10 They may be haloalkyls, and the definitions of each of these are as previously explained.

[0089] In this specification, thio is "-SR thio As a substituent that can be represented as ", where R thio is, respectively, of substitution or non-substitution, C 1-10 Alkyl, C 2-10 Alkenyl, C 3-10 Carbocycle, C 3-10 Cycloalkyl, C 6-30 Aryl, 3 to 30-membered heterocycle, C 1-10 They may be haloalkyls, and the definitions of each of these are as previously explained.

[0090] In this specification, the imine or imino is a monovalent primary ketimine (-C(NH)R i-1 ), secondary ketimine (-C(NR i-2 )R i-1 ), primary aldimin(-C(NH)H), secondary aldimin(-C(NR i-1 It is intended to have a meaning that encompasses ) H). In this case, R i-1 and R i-2 Is Each independently, C 1-10 Alkyl, C 2-10 Alkenyl, C 3-10 Carbocycle, C 3-10 Cycloalkyl, C 6-30 Aryl, 3 to 30-membered heterocycle, C 1-10They may be haloalkyls, each of which may be substituted or unsubstituted, and the definitions of each are as previously explained.

[0091] In this specification, sulfone is "-S(=O)2R s As a substituent that can be represented as ", where R s is, respectively, of substitution or non-substitution, C 1-10 Alkyl, C 2-10 Alkenyl, C 3-10 Carbocycle, C 3-10 Cycloalkyl, C 6-30 Aryl, 3 to 30-membered heterocycle, C 1-10 They may be haloalkyls, and the definitions of each of these are as previously explained.

[0092] In this specification, phosphoric acid is "-OP(=O)(OH)2" or "-OP(=O)(OH)(OR P As a substituent that can be represented as )", wherein R P is, respectively, of substitution or non-substitution, C 1-10 Alkyl, C 2-10 Alkenyl, C 3-10 Carbocycle, C 3-10 Cycloalkyl, C 6-30 Aryl, 3 to 30-membered heterocycle, C 1-10 They may be haloalkyls, and the definitions of each of these are as previously explained.

[0093] compound

[0094] The compound according to the present invention is a compound represented by the following chemical formula I:

[0095] [Chemical Formula I]

[0096]

[0097] In the above formula,

[0098] Het is a 5 to 8-membered heterocycle comprising at least one heteroatom among N, O, S, and P as a constituent element, and

[0099] Z is O or S, and

[0100] n1 is an integer from 0 to 4, and when n1 is plural, R 1 They are identical or different from each other,

[0101] R 1 Each independently, halogen, cyano, nitro, SF5, OCN, SCN, Si(R 15 )3, OR 4 , NR 5 R 6 , C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O)2R 9 , OS(O)2NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O)2R 9 or N(R 10 )S(O)2NR 11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C3-20 Cycloalkenyl; or each halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 It is an aryl or pentagonal or hexacyclic heterocycle;

[0102] R 2 is hydrogen, halogen, cyano, nitro, SF5, OCN, SCN, Si(R 15 )3, OR 4 , NR 5 R 6 , C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O)2R 9, OS(O)2NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O)2R 9 or N(R 10 )S(O)2NR 11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or each halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 It is an aryl or pentagonal or hexacyclic heterocycle;

[0103] R 3 Silver is hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O)2NR 11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl C 3-20 Cycloalkenyl; C 1-6 Alkoxy or halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 Aril is;

[0104] Q are halogen, cyano, nitro, SF5, OCN, SCN, Si(R), respectively. 15 )3, OR 4 , NR 5 R 6, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O)2R 9 , OS(O)2NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O)2R 9 , N(R 10 )S(O)2NR 11 R 12 and R 14 C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 It is an aryl, 5-membered or 30-membered heterocycle;

[0105] X is independently O or S;

[0106] R 4 Each independently hydrogen, halogen, and C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0107] R 4a are independently hydrogen, C 1-6 alkyl or C 1-6 It is a haloalkyl;

[0108] R 5 are independently hydrogen, NR 5a R 6a , C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O)2NR 11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0109] R 5a Each independently hydrogen or C 1-6 It is alkyl;

[0110] R 6 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 It is a cycloalkenyl;

[0111] R 6a are independently hydrogen, C 1-6 Alkyl, C(O)R13 or C(O)OR 13 is;

[0112] R 7 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0113] R 7a C each independently 1-6 alkyl or C 1-6 It is a haloalkyl;

[0114] R 8Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0115] R 8a C each independently 1-6 alkyl or C 1-6 It is a haloalkyl;

[0116] R 9 are independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0117] R 9a C each independently 1-6 alkyl or C 1-6 It is a haloalkyl;

[0118] R 10 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7a, C(O)OR 8a , C(O)NR 11 R 12 , S(O) m R 9a or S(O)2NR 11 R 12 And;

[0119] R 10a are independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 It is a haloalkinyl;

[0120] R 11 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11a R 12 , OR 4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11a R 12 , NR 5a R6a , OC(O)R 7a and N(R 10a )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0121] R 11a are independently hydrogen, C 1-6 Alkyl, C 2-6 Alkenyl or C 2-6 It is alkynyl;

[0122] R 12 are independently hydrogen, NR 5a R 6a , C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkinyl, C 2-6 Haloalkinyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O)2NR 11 R 12 ; or halogen, cyano, nitro, C respectively 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR4a , C 1-6 Alkoxy, S(O) m R 9a , S(O)2NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 3 substituents independently selected from the group consisting of 6-30 Ariligo;

[0123] R 13 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 It is a cycloalkenyl;

[0124] R 14 Each independently halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or each halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 It is an aryl or pentagonal or hexacyclic heterocycle;

[0125] R 15 are independently, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl; or each halogen, cyano, nitro, C 1-4 Alkyl, C 1-4 Haloalkyl, OR 4a and S(O) m R 9a C that is arbitrarily substituted with 0 to 4 substituents independently selected from the group consisting of 3-20 Cycloalkyl or C 3-20 Cycloalkenyl; or halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) mR 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 5 substituents independently selected from the group consisting of 6-30 Aril is;

[0126] m is independently 0, 1, or 2.

[0127] In one specific example, Z can be O.

[0128] In one specific example, R 3 It can be H.

[0129] In one specific example, Het The ring represented by may be a 5 to 8-membered heterocycle in which one of the constituent elements of the heterocycle is N and the rest are C.

[0130] In one specific example, Het The ring represented by may be a 5 to 8-membered heterocycle in which two of the constituent elements of the heterocycle are N and the rest are C.

[0131] In one specific example, Het The ring represented by may be a 5 to 8-membered heterocycle in which one of the constituent elements of the heterocycle is N, one is O, and the rest are C.

[0132] In one specific example, Het The ring represented by may be a 5 to 8-membered heterocycle in which one of the constituent elements of the heterocycle is N, one is S, and the rest are C.

[0133] In one specific example, Het The ring represented by may be a 5 to 8-membered heterocycle in which two of the constituent elements of the heterocycle are N, one is O, and the rest are C.

[0134] In one specific example, Het The ring represented by may be a 5 to 8-membered heterocycle in which two of the constituent elements of the heterocycle are N, one is S, and the rest are C.

[0135] In one specific example, Het The ring represented by may be any one selected from the following heterocycle groups.

[0136] [Heterocycle Group]

[0137]

[0138] In the above heterocycle group, the hydrogen bonded to the carbon is R as defined in Chemical Formula I. 1 It can be replaced with. Specifically, R 1 Silver halogen, cyano, nitro, C 1-4 Alkyl, C 1-6 Haloalkyl, C(X)R 7 , C(O)OR 8 , OC(O)R 7 , C 3-20 Cycloalkyl, C 6-30 It can be an aryl, 5-membered or 6-membered heterocycle. R 1 It may be substituted with any one of the substituents selected from the “substituent group” described in this specification.

[0139] Here, R 7 and R 8 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Alkinyl, C 3-20 Cycloalkyl or C 6-30 It may be an aryl. However, the R listed above 7 and R 8 Each can be independently substituted with any one of the substituents selected from the “substituent group” described in this specification.

[0140] In one specific example, the compound represented by the above chemical formula I may be the compound represented by the following chemical formula I-1.

[0141] [Chemical Formula I-1]

[0142]

[0143] In the above chemical formula I-1, n1, R 1 , R 2 , R 3 , Z and Q are as defined in Chemical Formula I.

[0144] Specifically, in the above chemical formula I-1,

[0145] n1 can be 0 or 1, and

[0146] R 1 Silver is Cl, F, Br, I, cyano, nitro, C 1-4 Alkyl, C 1-6 Haloalkyl, C(X)R 7 , C(O)OR 8 , OC(O)R 7 , C 3-20 Cycloalkyl, C 6-30 It can be an aryl, 5-membered or 6-membered heterocycle. Here, R 7 and R 8 Each independently hydrogen, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Alkinyl, C 3-20 Cycloalkyl or C 6-30 It could be Aril,

[0147] R 2 is hydrogen, Cl, F, Br, I, or C 1-4 It can be alkyl, and R 3 is hydrogen, Cl, F, Br, I, C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-20 Cycloalkyl or C 6-30 It is an aryl, Z is oxygen, and Q is a substituted or unsubstituted C 6-30It can be an aryl or 5-won or 30-won heterocycle.

[0148] More specifically, in the above chemical formula I-1,

[0149] n1 can be 0 or 1, and R 1 halogen or C 1-4 It can be alkyl, and R 2 can be hydrogen, and R 3 is hydrogen, Z is oxygen, and Q is substituted or unsubstituted C 6-30 It could be Aril.

[0150] In one specific example, Q is halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 4 substituents independently selected from each of the groups consisting of 6-30 It can be an aryl or a 5-membered or 6-membered heterocycle.

[0151] In one specific example, Q is halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 1-6 Alkoxy, C(X)R 7, C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with 0 to 2 substituents each independently selected from the group consisting of 6-30 It could be Aril.

[0152] In one specific example, Q is halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a C that is arbitrarily substituted with one or two substituents independently selected from each of the groups consisting of 6-30 It could be Aril.

[0153] In one specific example, Q is the non-substituted C 6-30 It could be Aril.

[0154] In one specific example, Q may be any aryl selected from the following aryl groups (in the aryl groups, dotted lines indicate connections):

[0155] [Arilgi Group]

[0156]

[0157]

[0158]

[0159] In one specific example, the compound represented by the above chemical formula I may be represented by the following chemical formula Ia:

[0160] [Chemical Formula Ia]

[0161]

[0162] In the above formula,

[0163] R 1Q is hydrogen, halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a Selected from a group consisting of,

[0164] R 2Q is hydrogen, halogen, nitro, OR 4 , NR 5 R 6 , C 1-4 Haloalkyl, C 2-4 Haloalkenyl and C 2-6 Selected from a group consisting of alkoxy,

[0165] R 3Q is hydrogen, halogen, OR 4 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl and C 2-4Selected from a group consisting of haloalkenyls, and

[0166] R 4Q , R 5Q Each is independently hydrogen, halogen, or C 1-4 It is a haloalkyl, and

[0167] Z, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 7a is as defined in Chemical Formula I.

[0168] In one specific example, the compound represented by the above chemical formula I may be represented by any one selected from the group consisting of the following chemical formulas Ia-1 to Ia-8.

[0169] [Chemical Formula Ia-1]

[0170]

[0171] [Chemical Formula Ia-2]

[0172]

[0173] [Chemical Formula Ia-3]

[0174]

[0175] [Chemical Formula Ia-4]

[0176]

[0177] [Chemical Formula Ia-5]

[0178]

[0179] [Chemical Formula Ia-6]

[0180]

[0181] [Chemical Formula Ia-7]

[0182]

[0183] [Chemical Formula Ia-8]

[0184]

[0185] In the above formula,

[0186] R 1Q Halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a Selected from a group consisting of,

[0187] R 2Q is halogen, nitro, OR 4 , NR 5 R 6 , C 1-4 Haloalkyl, C 2-4 Haloalkenyl and C 1-6 Selected from a group consisting of alkoxy,

[0188] R 3Q is halogen, OR 4 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl and C 2-4 Selected from a group consisting of haloalkenyls, and

[0189] R 4Q , R 5Q Each independently is a halogen or C 1-4 It is a haloalkyl, and

[0190] Z, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 7a is as defined in Chemical Formula I.

[0191] In one specific example, the compound represented by the above chemical formula I may be a compound represented by the following chemical formula Ib:

[0192] [Chemical Formula Ib]

[0193]

[0194] In the above formula,

[0195] R 1Q is hydrogen, halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a Selected from a group consisting of,

[0196] R 2Q is hydrogen, halogen, nitro, OR 4 , NR 5 R 6 , C 1-4 Haloalkyl, C 2-4 Haloalkenyl and C 1-6Selected from a group consisting of alkoxy,

[0197] R 3Q is hydrogen, halogen, OR 4 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl and C 2-4 Selected from a group consisting of haloalkenyls, and

[0198] R 4Q , R 5Q Each is independently hydrogen, halogen, or C 1-4 It is a haloalkyl, and

[0199] R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 7a is as defined in Chemical Formula I.

[0200] In one specific example, the compound represented by the above chemical formula I may be represented by any one selected from the group consisting of the following chemical formulas Ib-1 to Ib-8.

[0201] [Chemical Formula Ib-1]

[0202]

[0203] [Chemical Formula Ib-2]

[0204]

[0205] [Chemical Formula Ib-3]

[0206]

[0207] [Chemical Formula Ib-4]

[0208]

[0209] [Chemical Formula Ib-5]

[0210]

[0211] [Chemical Formula Ib-6]

[0212]

[0213] [Chemical Formula Ib-7]

[0214]

[0215] [Chemical Formula Ib-8]

[0216]

[0217] In the above formula,

[0218] R 1Q Halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1-4 Haloalkyl, C 2-4 Haloalkenyl, C 1-6 Alkoxy, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O)2NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a Selected from a group consisting of,

[0219] R 2Q is halogen, nitro, OR 4 , NR 5 R 6 , C 1-4 Haloalkyl, C 2-4 Haloalkenyl and C 1-6 Selected from a group consisting of alkoxy,

[0220] R 3Q is halogen, OR 4 , C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkinyl, C 1-4 Haloalkyl and C 2-4Selected from a group consisting of haloalkenyls, and

[0221] R 4Q , R 5Q Each independently is a halogen or C 1-4 It is a haloalkyl.

[0222] In one specific example, the compound represented by the above chemical formula I may be represented by any one selected from the following chemical formula group:

[0223]

[0224] Control composition

[0225] The pest control composition according to the present invention may contain at least one of a compound, its acceptable salt, its solvate, its enantiomer, its diastereomer, and its tautomer.

[0226] The pest control composition of the present invention may preferably be prepared in the form of a wettable powder, suspension, emulsion, turbidity, microemulsion, liquid, dispersible liquid, granular wettable powder, granule, powder, liquid wettable powder, floating granule, or tablet, but may also be prepared in other forms as needed.

[0227] Plants to which the control composition of the present invention can be applied include, but are not limited to, plants such as sweet potatoes, pumpkins, Korean melons, tomatoes, watermelons, cucumbers, eggplants, strawberries, chili peppers, tobacco, carrots, peanuts, radishes, lettuce, spinach, pears, burdock, onions, sesame, ginseng, soybeans, grapes, peaches, or potatoes that develop root galls caused by plant parasitic nematodes, specifically root-knot nematodes.

[0228] The pest control composition of the present invention may, for example, have a liquid form that is easy to spray, but may be formed in any form as long as it maintains the nematicidal activity of the nematode.

[0229] The pest control composition of the present invention may be formulated, for example, by mixing a surfactant, i.e., an emulsifier and / or a dispersant and / or a foam-forming agent, with an extender, i.e., a liquid solvent and / or a solid carrier.

[0230] Surfactants can be substances with high surface activity and are amphiphilic substances having hydrophilic and lipophilic molecular groups within their molecules; possessing excellent cleaning, dispersing, emulsifying, solubilizing, wetting, bactericidal, foaming, and penetrating powers, they function to wet, disintegrate, disperse, and emulsify in order to effectively manifest medicinal effects. The above surfactants include alkyl (C 8-12 )Benzenesulfonate, alkyl(C 3-6 )Naphthalenesulfonate, dialkyl(C 3-6 )Naphthalenesulfonate, dialkyl(C 8-12 )sulfosuccinate, ligninsulfonate, naphthalenesulfosuccinate formalin condensate, alkyl(C 8-12 )Naphthalenesulfonate formalin condensate, polyoxyethylenealkyl(C 8-12 ) Sodium or calcium salts of sulfons such as phenylsulfonate, alkyl(C 8-12 )sulfate, polyoxyethylenealkyl(C 8-12 )sulfate, polyoxyethylenealkyl(C 8-12 Anionic surfactants such as sodium or calcium salts of sulfates like phenyl sulfate, sodium or calcium salts of succinates like polyoxyalkylene succinate, and polyoxyethylenealkyl (C 8-12 )ether, polyoxyethylenealkyl(C 8-12 )phenyl ether, dioxyethylenealkyl(C 8-12 Nonionic surfactants, such as phenyl polymers, can be used alone or in a mixture of two or more types.

[0231] Diluents can be classified into solid diluents and liquid diluents depending on their properties. As solid diluents, diluents with high absorption capacity may be particularly desirable when making wettable powders. It may be desirable for liquid diluents and solvents to be stable and not undergo phase separation even at 0°C. Liquid diluents include water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butyline carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, and ethyl Acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesethyl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG), propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate,Triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and high molecular weight alcohols, e.g., amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc., may be used. As solid diluents, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomite, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, whole wheat flour (wheatmeal), soybean powder, pumice, wood flour, walnut shells, lignin, etc., may be used.

[0232] When water is used as an extender, for example, an organic solvent may also be used as a co-solvent. Suitable liquid solvents include mainly aromatic compounds such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride; aliphatic hydrocarbons such as cyclohexane or paraffin, for example, mineral oil fractions, mineral oil, and vegetable oil; alcohols such as butanol or glycol and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; strong polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water.

[0233] Suitable solid carriers are, for example, crushed natural minerals such as ammonium salts and kaolin, clay, talc, chalk, quartz, atapalgit, montmorillonite, or diatomite, and crushed synthetic minerals such as highly dispersed silica, alumina, and silicates. Suitable solid carriers for granulation are, for example, crushed and classified natural rocks such as calcite, marble, pumice, merciolite, and dolomite, synthetic granules of inorganic and organic powders, and granules of organic materials such as sawdust, coconut shells, corn cobs, and tobacco stalks. Suitable emulsifiers and / or foam-forming agents are, for example, nonionic and anionic emulsifiers, polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters and alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, or protein hydrolysates. Suitable dispersants are, for example, lignin sulfite waste liquid and methylcellulose. Suitable adhesives may be natural and synthetic polymers in powder, granular, or latex form, such as carboxymethylcellulose, gum arabic, polyvinyl alcohol, and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids, used in the formulation. Other additives may be mineral oils and vegetable oils. Suitable coloring agents may be inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes, and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc.

[0234] The laxative is one or more selected from the group consisting of benoxacor, cloquintocet, ciometrinil, dichlormide, dicycloron, dietholate fenchlorazole, fencloim, flurazole, fluoxofenim, furilazole, isooxadiphene, mefenpyr, mefenate, naphthalic anhydride, 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane and oxavetrinil.

[0235] The control composition of the present invention may be used as a mixture with other known nematicides or preparations thereof, and may be applied in the form of a ready mix or as an individual preparation, such as a tank mix in which the nematicidal active compound is mixed at the time of use. Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, bird repellents, growth substances, plant nutrients, and soil conditioners, are also possible. For specific application purposes, particularly when applied in post-emergence methods, it may also be advantageous to impregnate the preparation with a plant-tolerant mineral oil or vegetable oil (e.g., the commercially available product "Rako Binol") or an ammonium salt, such as ammonium sulfate or ammonium thiosulfate, as an additional additive.

[0236] The pest control composition of the present invention may be used as is, in its formulation form, or in forms of use that can be prepared by further diluting these formulations, e.g., immediate-use solutions, suspensions, emulsions, powders, pastes, and granules. These are used by conventional methods, e.g., by pouring, spraying, atomizing, spreading, or broadcasting.

[0237] In the following, the present invention is described in detail with reference to examples in order to specifically explain the disclosure of the present invention as described above and the intended functions and effects of the present invention. However, the examples may be modified in various different forms, and the scope of this specification is not to be interpreted as being limited only to these examples. It is emphasized that the examples are provided to represent the present invention and to explain it more specifically to those skilled in the art.

[0238] <Example 1>

[0239] Synthesis of the compound of chemical formula Ib-1-1

[0240]

[0241] Imidazol[1,5-a]pyridine-1-carboxylic acid (0.31 mmol, 50 mg) and 2-fluorobenzenesulfonamide (0.31 mmol, 54 mg) were dissolved in dichloromethane (DCM) in a reactor, after which N3-(ethylcarbonimidoyl)-N1,N1-dimethyl-1,3-propanediamine hydrochloride (1:1) (EDC·HCl) and 4-dimethylaminopyridine (DMAP) were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, followed by evaporative drying to remove the solvent. The mixture was then purified by column chromatography to obtain a compound of the chemical formula Ib-1-1 (yield 40%).

[0242] 1 H NMR (500 MHz, DMSO-d6) δ 8.39 (d, 1H), 8.32 (s, 1H), 8.19 (d, 1H), 7.87 (td, 1H), 7.49 (tdd, 1H), 7.26 (t, 1H), 7.19 (dd, 1H), 7.01 (dd, 1H), 6.78 (td, 1H).

[0243] <Example 2>

[0244] Synthesis of the compound of chemical formula Ib-1-2

[0245]

[0246] Imidazō[1,5-a]pyridine-1-carboxylic acid (0.62 mmol, 100 mg) and 2-chlorobenzenesulfonamide (0.62 mmol, 118 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-1-2 was obtained by purification by column chromatography (yield 74%).

[0247] 1H NMR (500 MHz, DMSO-d6) δ 8.40 (dt, 1H), 8.35 (s, 1H), 8.32 - 8.26 (m, 2H), 8.20 (d, 1H), 8.07 (dd, 1H), 7.01 (ddd, 1H), 6.93 - 6.87 (m, 2H), 6.78 (td, 1H).

[0248] <Example 3>

[0249] Synthesis of the compound of chemical formula Ib-1-3

[0250]

[0251] Imidazō[1,5-a]pyridine-1-carboxylic acid (0.62 mmol, 100 mg) and 2-trifluoromethylbenzenesulfonamide (0.62 mmol, 139 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4 and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-1-3 was obtained by purification by column chromatography (yield 77%).

[0252] 1 H NMR (500 MHz, DMSO-d6) δ 8.39 (dd, 1H), 8.33 (s, 1H), 8.29 (d, 1H), 8.22 (d, 1H), 7.74 (qd, 3H), 7.63 (t, 1H), 7.03 - 6.97 (m, 1H), 6.77 (d, 1H).

[0253] <Example 4>

[0254] Synthesis of the compound of chemical formula Ib-1-4

[0255]

[0256] Imidazol[1,5-a]pyridine-1-carboxylic acid (0.62 mmol, 100 mg) and 2-nitrobenzenesulfonamide (0.62 mmol, 125 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4 and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-1-4 was obtained by purification by column chromatography (yield 86%).

[0257] DMSO-d6) δ 8.38 (dt, 1H), 8.32 (s, 1H), 8.25 (d, 1H), 8.14 (dd, 1H), 7.69 - 7.57 (m, 3H), 6.99 (ddd, 1H).

[0258] <Example 5>

[0259] Synthesis of the compound of chemical formula Ib-1-5

[0260]

[0261] Imidazō[1,5-a]pyridine-1-carboxylic acid (0.62 mmol, 100 mg) and 2-trifluoromethoxybenzenesulfonamide (0.62 mmol, 149 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4 and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-1-5 was obtained by purification by column chromatography (yield 65%).

[0262] 1 H NMR (500 MHz, DMSO-d6) δ 8.39 (dt, 1H), 8.34 (s, 1H), 8.20 (d, 1H), 8.04 (dd, 1H), 7.56 (td, 1H), 7.44 (td, 1H), 7.33 (dt, 1H), 6.99 (ddd, 1H), 6.77 (td, 1H).

[0263] <Example 6>

[0264] Synthesis of the compound of chemical formula Ib-2-1

[0265]

[0266] Imidazol[1,5-a]pyridine-1-carboxylic acid (0.31 mmol, 50 mg) and 3-fluorobenzenesulfonamide (0.31 mmol, 54 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-2-1 was obtained by purification by column chromatography (yield 44%).

[0267] 1 H NMR (500 MHz, DMSO-d6) δ 8.57 (dd, 1H), 8.55 (s, 1H), 7.96 (d, 1H), 7.88 (dt, 1H), 7.82 (dt, 1H), 7.74 - 7.66 (m, 1H), 7.58 (td, 1H), 7.34 - 7.26 (m, 1H), 7.01 (td, 1H).

[0268] <Example 7>

[0269] Synthesis of the compound of chemical formula Ib-2-2

[0270]

[0271] Imidazol[1,5-a]pyridine-1-carboxylic acid (0.31 mmol, 50 mg) and 3-nitrobenzenesulfonamide (0.31 mmol, 54 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-2-2 was obtained by purification by column chromatography (yield 76%).

[0272] 1 H NMR (500 MHz, DMSO-d6) δ 8.80 (t, 1H), 8.62 - 8.56 (m, 2H), 8.52 (ddd, 1H), 8.45 (dt, 1H), 8.01 - 7.91 (m, 2H), 7.30 (ddd, 1H), 7.01 (td, 1H).

[0273] <Example 8>

[0274] Synthesis of the compound of chemical formula Ib-3-1

[0275]

[0276] Imidazol[1,5-a]pyridine-1-carboxylic acid (1.23 mmol, 200 mg) and para-toluenesulfonamide (1.23 mmol, 211 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4 and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-3-1 was obtained by purification by column chromatography (yield 51%).

[0277] 1 H NMR (500 MHz, Chloroform-d) δ 8.21 (d, 1H), 8.14 (s, 1H), 8.10 (dd, 3H), 7.36 (d, 2H), 7.18 (ddd, 1H), 6.89 (t, 1H), 2.44 (s, 3H).

[0278] <Example 9>

[0279] Synthesis of the compound of chemical formula Ib-3-2

[0280]

[0281] Imidazō[1,5-a]pyridine-1-carboxylic acid (1.23 mmol, 200 mg) and 4-fluorobenzenesulfonamide (1.23 mmol, 216 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4 and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-3-2 was obtained by purification by column chromatography (yield 56%).

[0282] 1 H NMR (500 MHz, DMSO-d6) δ 8.56 (d, 1H), 8.54 (s, 1H), 8.14 - 8.06 (m, 2H), 7.95 (d, 1H), 7.47 (t, 2H), 7.28 (dd, 1H), 6.99 (t, 1H).

[0283] <Example 10>

[0284] Synthesis of the compound of chemical formula Ib-3-3

[0285]

[0286] Imidazol[1,5-a]pyridine-1-carboxylic acid (1.23 mmol, 200 mg) and 4-trifluoromethylbenzenesulfonamide (1.23 mmol, 278 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, and the solvent was removed by evaporative drying. Subsequently, the compound of the chemical formula Ib-3-3 was obtained by purification by column chromatography (yield 63%).

[0287] 1 H NMR (500 MHz, DMSO-d6) δ 8.57 (d, 2H), 8.24 (d, 2H), 8.04 (d, 2H), 7.94 (d, 1H), 7.29 (dd, 1H), 7.01 (t, 1H).

[0288] <Example 11>

[0289] Synthesis of the compound of chemical formula Ib-3-4

[0290]

[0291] Imidazō[1,5-a]pyridine-1-carboxylic acid (1.23 mmol, 200 mg) and 4-trifluoromethoxybenzenesulfonamide (1.23 mmol, 297 mg) were dissolved in DCM in a reactor, followed by the addition of EDC·HCl and DMAP, and the mixture was stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, and the solvent was removed by evaporative drying. The mixture was then purified by column chromatography to obtain a compound of the chemical formula Ib-3-4 (yield 51%).

[0292] 1 H NMR (500 MHz, DMSO-d6) δ 8.63 - 8.47 (m, 2H), 8.23 ​​- 8.08 (m, 2H), 7.96 (dd, 1H), 7.63 (d, 2H), 7.29 (d, 1H), 7.01 (d, 1H).

[0293] <Example 12>

[0294] Synthesis of the compound of chemical formula Ib-4-1

[0295]

[0296] Imidazō[1,5-a]pyridine-1-carboxylic acid (0.62 mmol, 100 mg) and 2-chloro-5-methoxybenzenesulfonamide (0.62 mmol, 137 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-4-1 was obtained by purification by column chromatography (yield 30%).

[0297] 1H NMR (500 MHz, DMSO-d6) δ 8.59 (d, 2H), 7.93 (d, 1H), 7.63 (d, 1H), 7.55 (d, 1H), 7.34 - 7.23 (m, 2H), 7.01 (t, 1H), 3.86 (s, 3H).

[0298] <Example 13>

[0299] Synthesis of the compound of chemical formula Ib-4-2

[0300]

[0301] Imidazō[1,5-a]pyridine-1-carboxylic acid (0.31 mmol, 60 mg) and 2,5-difluorobenzenesulfonamide (0.31 mmol, 60 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-4-2 was obtained by purification by column chromatography (yield 74%).

[0302] 1 H NMR (500 MHz, DMSO-d6) δ 8.61 - 8.55 (m, 2H), 7.99 - 7.93 (m, 1H), 7.77 (ddd, 1H), 7.64 (ddt, 1H), 7.52 (td, 1H), 7.34 - 7.27 (m, 1H), 7.02 (td, 1H).

[0303] <Example 14>

[0304] Synthesis of the compound of chemical formula Ib-5-1

[0305]

[0306] Imidazō[1,5-a]pyridine-1-carboxylic acid (0.31 mmol, 60 mg) and 3,4-difluorobenzenesulfonamide (0.31 mmol, 60 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4 and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-5-1 was obtained by purification by column chromatography (yield 26%).

[0307] 1 H NMR (500 MHz, DMSO-d6) δ 8.62 - 8.53 (m, 2H), 8.07 (ddd, 1H), 7.97 (d, 1H), 7.73 (dt, 1H), 7.36 - 7.26 (m, 1H), 7.01 (td, 1H).

[0308] <Example 15>

[0309] Synthesis of the compound of chemical formula Ib-6-1

[0310]

[0311] Imidazō[1,5-a]pyridine-1-carboxylic acid (0.31 mmol, 50 mg) and 3,5-dichlorobenzenesulfonamide (0.31 mmol, 70 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-6-1 was obtained by purification by column chromatography (yield 82%).

[0312] 1 H NMR (500 MHz, DMSO-d6) δ 8.59 (d, 2H), 8.01 (dd, 4H), 7.32 (ddd, 1H), 7.03 (td, 1H).

[0313] <Example 16>

[0314] Synthesis of the compound of chemical formula Ib-7-1

[0315]

[0316] Imidazō[1,5-a]pyridine-1-carboxylic acid (0.31 mmol, 60 mg) and 2,4-difluorobenzenesulfonamide (0.31 mmol, 60 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4, and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-7-1 was obtained by purification by column chromatography (yield 74%).

[0317] 1 H NMR (500 MHz, DMSO-d6) δ 8.59 - 8.57 (m, 1H), 8.56 (s, 1H), 8.11 - 8.02 (m, 1H), 7.94 (d, 1H), 7.53 (t, 1H), 7.36 (dt, 1H), 7.29 (dd, 1H), 7.01 (td, 1H).

[0318] <Example 17>

[0319] Synthesis of the compound of chemical formula Ib-8

[0320]

[0321] Imidazol[1,5-a]pyridine-1-carboxylic acid (0.31 mmol, 50 mg) and benzenesulfonamide (0.31 mmol, 54 mg) were dissolved in DCM in a reactor, and then EDC·HCl and DMAP were added and stirred under reflux overnight. After the reaction was complete, the organic layer was washed with water and brine, and subsequently, moisture was removed from the organic layer using MgSO4 and the solvent was removed by evaporative drying. Subsequently, the compound of chemical formula Ib-8 was obtained by purification by column chromatography (yield 53%).

[0322] 1H NMR (500 MHz, DMSO-d6) δ 8.44 (d, 1H), 8.38 (s, 1H), 8.11 (d, 1H), 7.98 - 7.90 (m, 2H), 7.50 (qd, 3H), 7.09 (dd, 1H), 6.84 (t, 1H).

[0323] <Experimental Example>

[0324] Mortality Test: Root-knot Nematode In-vitro activity test

[0325] Since root-knot nematodes are obligate parasites, root-knot nematodes were inoculated into the roots of tomatoes (Seokwang, Farmhannong Co., Ltd.) and cultivated in the research institute's greenhouse (25±5℃) for approximately 6 weeks. Nematodes were isolated from the formed roots and used in the experiment. The gall-forming tomato roots were thoroughly washed with running water, finely chopped into pieces smaller than 1 cm, and placed in an Erlenmeyer flask. A 0.5% sodium hypochlorite solution (NaOCl) was poured into the flask, and the flask was shaken vigorously for 3 minutes to remove the membrane surrounding the egg sac. The solution was then filtered through a 65 μm sieve to remove root debris, and the resulting solution was filtered again through a 25 μm sieve to harvest pure nematode eggs. The isolated root-knot nematode eggs were placed in a 25℃ incubation chamber. Baermann funnel Larvae were hatched using a triangular funnel according to the method. The hatched second-instar larvae were collected in a beaker, and the nematode density was adjusted to 300 larvae per ml using a microscope.

[0326] In the examples, the compound of formula Ib-2-1 (Example 6), the compound of formula Ib-2-2 (Example 7), the compound of formula Ib-3-1 (Example 8), the compound of formula Ib-3-4 (Example 11), the compound of formula Ib-4-2 (Example 13), the compound of formula Ib-6-1 (Example 15), and the compound of formula Ib-8 (Example 17) synthesized were selected as active substances.

[0327] Each selected compound was dissolved in dimethyl sulfoxide to a concentration 100 times the experimental concentration and added to each well of a 96-well plate in 1 µl aliquot, after which 99 µl of nematode solution was inoculated. The control group was treated with cadusafos dissolved in DMSO at a final concentration of 4 µg / ml, and the untreated group was treated with 1% DMSO.

[0328] After incubating each inoculated well at 25°C for 72 hours, the mortality rate (%) of root-knot nematodes in each well was investigated, and the results are shown in Table 1 below. In vitro The concentration of the compound used for the activity test was 50 ppm, and all experiments were repeated three times.

[0329] Chemical formula (Example) Mortality rate*(%, @ 50 ppm) Ib-2-1 (Example 6) 77 Ib-2-2 (Example 7) 41 Ib-3-1 (Example 8) 94 Ib-3-4 (Example 11) 74 Ib-4-2 (Example 13) 47 Ib-6-1 (Example 15) 44 Ib-8 (Example 17) 46

[0330] * Mortality rate = {(Initial number of root-knot nematodes - Number of nematodes after compound inoculation) / Initial number of root-knot nematodes} * 100

[0331] From the results of Table 1, it can be seen that the compound according to the present invention can effectively kill nematodes even at a relatively low concentration of 50 ppm. From these results, it will be understood that the compound according to the present invention can contribute to solving previously recognized problems.

Claims

Claim 1 Compounds represented by the following chemical formula Ia: [Chemical Formula Ia] In the above formula, n1 is an integer from 0 to 4, and when n1 is plural, R 1 are identical or different from each other, and R 1 Silver halogen, cyano, nitro, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 It is a haloalkinyl, and R 2 and R 3 Each independently hydrogen, halogen, cyano, nitro, and C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Haloalkenyl, C 2-6 Alkynyl or C 2-6 It is a haloalkinyl, Z is O or S, and R 1Q to R 5Q Each independently hydrogen, halogen, and C 1-4 Alkyl, C 1-4 Haloalkyl, nitro, and OR 4 Selected from a group consisting of, and R 4 is C 1-6 alkyl or C 1-6 It is a haloalkyl. Claim 2 delete Claim 3 delete Claim 4 delete Claim 5 delete Claim 6 In paragraph 1, Z is a compound of O. Claim 7 In paragraph 1, R 3 A compound that is hydrogen. Claim 8 delete Claim 9 In claim 1, the compound represented by the chemical formula Ia is a compound represented by any one selected from the group consisting of the following chemical formulas Ia-1 to Ia-8: [Chemical Formula Ia-1] [Chemical Formula Ia-2] [Chemical Formula Ia-3] [Chemical Formula Ia-4] [Chemical Formula Ia-5] [Chemical Formula Ia-6] [Chemical Formula Ia-7] [Chemical Formula Ia-8] In the above equation, R 1Q to R 5Q Each independently halogen, C 1-4 Alkyl, C 1-4 Haloalkyl, nitro, and OR 4 Selected from the group consisting of, and n1, R 1 , R 2 , R 3 , R 4 , Z is as defined in Paragraph 1. Claim 10 In claim 1, the compound represented by the above chemical formula Ia is a compound represented by the following chemical formula Ib: [Chemical Formula Ib] In the above equation, R 1Q to R 5Q Each independently hydrogen, halogen, and C 1-4 Alkyl, C 1-4 Haloalkyl, nitro, and OR 4 Selected from a group consisting of, and R 4 is as defined in Paragraph 1. Claim 11 In claim 1, the compound represented by the chemical formula Ia is a compound represented by any one selected from the group consisting of the chemical formulas Ib-1 to Ib-8: [Chemical Formula Ib-1] [Chemical Formula Ib-2] [Chemical Formula Ib-3] [Chemical Formula Ib-4] [Chemical Formula Ib-5] [Chemical Formula Ib-6] [Chemical Formula Ib-7] [Chemical Formula Ib-8] In the above formula, R 1Q to R 5Q Each independently halogen, C 1-4 Alkyl, C 1-4 Haloalkyl, nitro, and OR 4 Selected from a group consisting of, and R 4 is as defined in Paragraph 1. Claim 12 In claim 1, the compound represented by the chemical formula Ia is a compound represented by any one selected from the following chemical formula group: Claim 13 Acceptable salts of the compound according to paragraph 1, its enantiomers, its diastereomers, its solvates, its geometric isomers, or its tautomers. Claim 14 A control composition comprising at least one of the compound according to claim 1, its acceptable salt, its enantiomer, its diastereomer, its solvate, its geometric isomer, and its tautomer as an active substance. Claim 15 A control composition according to claim 14, wherein the mortality rate measured against nematodes is 40% or higher when the concentration of the active substance is 50 ppm.

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