Pest control agent

FIELD: chemistry.

SUBSTANCE: invention describes compositions for use as a pest control agents containing a compound of formula (I), or a salt of the said compound, acceptable in agriculture or horticulture, as an active ingredient or carrier which is acceptable in agriculture or horticulture: [chemical formula 1] , where Het₁ denotes an optionally substituted pyridyl, R₁ denotes hydroxyl, optionally substituted C_1-6alkylcarbonyloxy, optionally substituted C_1-6alkyloxy, or oxo, in the absence of a hydrogen atom in position 13, or the bond between position 5 and position 13 is a double bond in the presence of R₁ and a hydrogen atom in position 5, R₂ denotes hydroxyl, optionally substituted C_1-18alkylcarbonyloxy, benzoyloxy or C_1-6alkylsulphonyloxy, R₃ denotes a hydrogen atom, hydroxyl, optionally substituted C_1-18alkylcarbonyloxy, benzoyloxy, C_1-6alkylsulphonyloxy, benzoylsulphonyloxy, imidazolylthiocarbonyloxy, R₄ denotes a hydrogen atom, hydroxyl, optionally substituted C_1-18alkylcarbonyloxy, C₂-₆alkenylcarbonyloxy, C₂-₆alkynylcarbonyloxy, benzoyloxy, C₁-₆alkylsulphonyloxy, benzoylsulphonyloxy, benzyloxy, C_1-6alkyloxy, C_1-6alkyloxy-C_1-6alkyloxy, C_1-6alkylthio-C_1-6alkyloxy, C_1-6alkyloxy-C_1-6alkyloxy-C_1-6alkyloxy, C_1-6alkyloxycarbonyloxy, C_1-6alkylaminocarbonyloxy, tetrahydropyranyloxy, a saturated or unsaturated five- or six-member heterocyclic carbonyloxy, where the said heterocyclic part is selected from a group comprising pyridyl, thienyl, thiazolylpyrazinyl and imidazolyl, optionally substituted tieno[3,2-b]pyridylcarbonyloxy, 1H-indolylcarbonyloxy, imidazolylthiocarbonyloxy, or oxo, in the absence of a hydrogen atom in position 7, provided that the compound, where Het₁ denotes 3-pyridyl, R₁ denotes hydroxyl and each of R₂, R₃ and R₄ is acetyloxy, is excluded. Disclosed composition is also used in hemipterous pest control.

EFFECT: synthesis of a novel pyripyropen having significant insecticide activity.

22 cl, 29 tbl, 16 ex

Description

The present invention relates to compositions for application as a means of pest control that contains the derived peripherin as the active ingredient.

Peripherin A has inhibitory activity against ACAT (acyl-CoA: cholesterylester) and, as expected, it can be used, for example, for the treatment of diseases caused by accumulation of cholesterol, as described in Japan patent No. 2993767 (publication laid patent application of Japan No. 360895/1992) and Journal of Antibiotics (1993), 46(7), 1168-9.

In addition, analogs and derivatives of peripherin and their inhibitory activity against ACAT described in Journal of Society of Synthetic Organic Chemistry, Japan (1998), Vol. 56, No. 6, pp. 478-488, WO 94/09417, publication laid patent application of Japan No. 184158/1994, publication laid patent application of Japan No. 239385/1996, publication laid patent application of Japan No. 259569/1996, publication laid patent application of Japan No. 269062/1996, publication laid patent application of Japan No. 269063/1996, publication laid patent application of Japan No. 269064/1996, publication laid patent application of Japan No. 269065/1996, publication laid patent application of Japan No. 269066/1996, publication laid patent application of Japan No. 291164/1996 and Journal of Antibiotics (1997), 50(3), 229-36.

Further, in Applied and Environmental Microbiology (1995), 61(12), 4429-35 described that piripi is open A has insecticidal activity against larvae of Helicoverpa zea. In addition, in WO 2004/060065 described that peripherin A has insecticidal activity against larvae of Plutella xylostella L and Tenebrio molitor L. However, these documents do not provide specific descriptions of the insecticidal activity of peripherin A against other pests.

In addition, none of the above documents is not described insecticidal activity of analogs and derivatives of peripherin.

To date, described many compounds with insecticidal activity and used as a means of pest control. However, creates the problem of the presence of species of pests resistant to these compounds or poorly controlled these compounds. Therefore, there is still a need to develop new means of pest control, with high insecticidal activity.

The authors of the present invention discovered that derivatives of peripherin represented by the formula (I)have significant insecticidal activity.

The authors also found that peripherin A and its corresponding derivative represented by formula (Ia), have significant insecticidal activity against Hemiptera pests.

In addition, the authors of the present invention discovered new derivatives of peripherin, represented by formula (Ib), with significant insecticidal activity.

The present invention is based on these discoveries.

Thus, the purpose of the present invention is to develop a composition, useful as a means of pest control, which contains with significant insecticidal activity derived peripherin, as an active ingredient, and has had the desired effect, as safe for use. Another objective of the present invention is to develop a means of combating bugs pest control, which includes peripherin A and its corresponding derivative as an active ingredient and has the desired impact, as safe for use. Another objective of the present invention is to develop a new derived peripherin with significant insecticidal activity.

According to one aspect of the present invention developed a composition for use as a means of pest control, containing the compound represented by formula (I), or acceptable from the point of view of the agriculture and horticulture salt of the compounds as the active ingredient and acceptable from the point SP is of the agriculture and horticulture carrier:

[Chemical formula 1]

where

Het₁means optionally substituted 3-pyridyl,

R₁means hydroxyl,

optionally substituted C_1-6alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted C_2-6alkylcarboxylic,

optionally substituted C_1-6alkyloxy,

optionally substituted C_2-6alkenylacyl,

optionally substituted C_2-6alkyloxy,

optionally substituted benzyloxy or

oxo in the absence of a hydrogen atom in position 13, or

the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5,

R₂means hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted C_2-6alkylcarboxylic,

optionally substituted benzoyloxy, or

optionally substituted C_1-6alkylsulfonate,

R₃means a hydrogen atom

hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted C_2-6alkylcarboxylic,

optional for ewenny benzoyloxy,

optionally substituted C_1-6alkylsulfonate,

optionally substituted, benzosulfimide or

optionally substituted five - or six-membered heterocyclic, thiocarbonate, or

R₂and R₃together represent-O-CR₂'R₃'-O-, where R₂' and R₃'which may be identical or different, denote a hydrogen atom, a C_1-6alkyl, C_1-6alkyloxy, C_2-6alkenyl, optionally substituted phenyl or optionally substituted benzyl, or R₂' and R₃' together denote oxo or C_2-6alkylen, and

R₄means a hydrogen atom,

hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted C_2-6alkylcarboxylic,

optionally substituted benzoyloxy,

optionally substituted C_1-6alkylsulfonate,

optionally substituted, benzosulfimide,

optionally substituted benzyloxy,

optionally substituted C_1-6alkyloxy,

optionally substituted C_2-6alkenylacyl,

optionally substituted C_2-6alkyloxy,

C_1-6alkyloxy-C_1-6alkyloxy,

C_1-6alkylthio-C_1-6alkyloxy,

C_1-6alkyloxy-C_1-6alkyloxy-C_1-6alkylic and,

optionally substituted C_1-6allyloxycarbonyl,

optionally substituted C_1-6alkylaminocarbonyl,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic oxy,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy,

optionally substituted thieno[3,2-b]pyridylcarbonyl,

optionally substituted 1H-indolinecarboxylic,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate or

oxo in the absence of a hydrogen atom in position 7, provided that the compound, where

Het₁mean 3-pyridyl,

R₁means hydroxyl and

all R₂, R₃and R₄are the atomic charges excluded.

Further, according to another aspect of the present invention developed a composition for use as a means of combating agricultural Hemiptera pests containing the compound represented by formula (Ia), or acceptable from the point of view of the agriculture and horticulture salt of the compounds as the active ingredient and acceptable from the point of view of the agriculture and horticulture carrier:

[Chemical formula 2]

where

Het₂means optionally substituted 3-pyridyl,

R₁₁means hydroxyl,

optionally substituted C_1-6alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted C_2-6alkylcarboxylic,

optionally substituted C_1-6alkyloxy,

optionally substituted C_2-6alkenylacyl,

optionally substituted C_2-6alkyloxy,

optionally substituted benzyloxy or

oxo in the absence of a hydrogen atom in position 13, or

the relationship between position 5 and position 13 represents a double bond in the absence of R₁₁and the hydrogen atom in position 5,

R₁₂means hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted C_2-6alkylcarboxylic,

optionally substituted benzoyloxy, or

optionally substituted C_1-6alkylsulfonate,

R₁₃means a hydrogen atom,

hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted C_2-6alkylcarboxylic,

optionally substituted benzoyloxy,

optionally substituted Csub> 1-6alkylsulfonate,

optionally substituted, benzosulfimide or

optionally substituted five - or six-membered heterocyclic, thiocarbonate, or

R₁₂and R₁₃together represent-O-CR₁₂'R₁₃'-O-, where R₁₂' and R₁₃'which may be identical or different, denote a hydrogen atom, a C_1-6alkyl, C_1-6alkyloxy, C_2-6alkenyl, optionally substituted phenyl or optionally substituted benzyl, or R₁₂' and R₁₃' together represent oxo, or C_2-6alkylen, and

R₁₄means a hydrogen atom,

hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted C_2-6alkylcarboxylic,

optionally substituted benzoyloxy,

optionally substituted C_1-6alkylsulfonate,

optionally substituted, benzosulfimide,

optionally substituted benzyloxy,

optionally substituted C_1-6alkyloxy,

optionally substituted C_2-6alkenylacyl,

optionally substituted C_2-6alkyloxy,

C_1-6alkyloxy-C_1-6alkyloxy,

C_1-6alkylthio-C_1-6alkyloxy,

C_1-6alkyloxy-C_1-6alkyloxy-C_1-6alkyloxy,

long is Ino substituted C _1-6allyloxycarbonyl,

optionally substituted C_1-6alkylaminocarbonyl,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic oxy,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy,

optionally substituted thieno[3,2-b]pyridylcarbonyl,

optionally substituted 1H-indolinecarboxylic,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate or

oxo in the absence of a hydrogen atom in position 7.

In addition, the derived peripeteia of the present invention includes the compound represented by formula (Ib), or acceptable from the point of view of the agriculture and horticulture Sol specified connection:

[Chemical formula 3]

where

Het₁mean 3-pyridyl,

R₁means hydroxyl,

R₂and R₃represent propionyloxy or optionally substituted cyclic C_3-6alkylcarboxylic, and

R₄means hydroxyl,

optionally substituted cyclic C_3-6alkylcarboxylic,

optionally substituted benzoyloxy, or

optionally substituted saturated or unsaturated five - or pole is-membered heterocyclic, carbonyloxy.

Derivatives peripherin represented by the formula (I) or formula (Ib) of the present invention, show excellent action in the fight against agricultural and horticultural pests, harmful from the point of view of sanitation, insects, parasites of animals, barn pests, insect pests of clothing and household pests, and compositions containing the derivatives of peripherin as an active ingredient, can be successfully used as a new means of pest control.

Then, unexpectedly, it was found that from among compounds represented by formula (Ia), peripherin A has an effective action in the fight against bugs pest control. Thus, the composition of the present invention containing the compound represented by formula (Ia), including peripherin A, in particular, suitable for use as a means of combating bugs pest control.

The term "halogen"as used herein means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.

The terms "alkyl", "alkenyl" and "quinil", as used in this description, as a group or part of a group, respectively, denote alkyl, alkenylphenol and alkenylphenol the group of linear, branched and the cyclic type, or combined type, unless otherwise specified. In addition, for example, "C_1-6" b "C_1-6alkyl," as used in this description, as a group or part of a group, means that the number of carbon atoms in the alkyl group is 1-6. Further, in the case of cyclic alkyl, the number of carbon atoms is at least three.

The term "heterocyclic ring", as used herein, means a heterocyclic ring containing one or more, preferably one to four, heteroatoms, which may be the same or different, and selected from the group comprising atoms of nitrogen, oxygen and sulfur. Further, the expression "optionally substituted" alkyl, as used herein, means that one or more hydrogen atoms on the alkyl group may be substituted by one or more substituents, which may be the same or different. For the person skilled in the art it is obvious that the maximum number of substituents is determined by the number suitable for substitution of the hydrogen atoms on the alkyl group. This is true for functional groups other than alkyl groups.

3-Pyridyl, presents Het₁and Het₂is optionally substituted, and substituents include halogen atoms, C_1-4alkyl, C_1-4alkyloxy, nitro, cyano, formyl, t is iformity, triptoreline, triptoreline, triptorelin, trifloromethyl, acetyl, atomic charges. Preferred are halogen atoms and trifluoromethyl. More preferable, a chlorine atom and trifluoromethyl.

"C_1-6alkylcarboxylic"represented by R₁and R₂is optionally substituted, and substituents include halogen atoms, cyano, phenyl, triptoreline, triptoreline.

"C_1-18alkylcarboxylic"represented by R₂, R₃and R₄and R₁₂, R₁₃and R₁₄preferably means C_1-6alkylcarboxylic, more preferably, propionyloxy or cyclic C_3-6alkylcarboxylic. C_1-18alkylcarboxylic is optionally substituted, and substituents include halogen atoms, cyano, cyclic C_3-6alkyl, phenyl, triptoreline, triptoreline, pyridyl, pyridylthio. More preferred are halogen atoms, cyclic C_3-6alkyl and pyridyl.

"C_2-6alkenylboronic"represented by R₁, R₂, R₃and R₄and R₁₁, R₁₂, R₁₃and R₁₄is optionally substituted, and substituents include halogen atoms, cyano, phenyl, triptoreline, triptoreline.

"C_2-6alkylcarboxylic"represented by R₁, R₂, R₃and R₄and R₁₁, Rsub> 12, R₁₃and R₁₄is optionally substituted, and substituents include halogen atoms, cyano, phenyl, triptoreline, triptoreline.

"C_1-6alkyloxy"represented by R₁and R₄and R₁₁and R₁₄is optionally substituted, and substituents include halogen atoms; cyano; phenyl; triptoreline; triptoreline; C_1-6alkylsulphonyl, optionally substituted by a halogen atom; and (C_1-6alkylcarboxylic, optionally substituted by a halogen atom.

"C_2-6alkenylacyl"represented by R₁and R₄and R₁₁and R₁₄is optionally substituted, and substituents include halogen atoms; cyano; phenyl; triptoreline; triptoreline; C_1-6alkylsulphonyl, optionally substituted by a halogen atom; and (C_1-6alkylcarboxylic, optionally substituted by a halogen atom.

"C_2-6alkyloxy"represented by R₁and R₄and R₁₁and R₁₄is optionally substituted, and substituents include halogen atoms; cyano; phenyl; triptoreline; triptoreline; C_1-6alkylsulphonyl, optionally substituted by a halogen atom; and (C_1-6alkylcarboxylic, optionally substituted by a halogen atom.

Phenyl in "benzyloxy"represented by R₁and R₄and R₁₁and R₁₄is not necessarily samewe the tion, and substituents include halogen atoms; C_1-6alkyloxy, optionally substituted by a halogen atom; C_1-6alkyl, optionally substituted by a halogen atom; C_1-6alkylsulphonyl, optionally substituted by a halogen atom; C_1-6alkylcarboxylic, optionally substituted by a halogen atom; C_1-6alkylcarboxylic, optionally substituted by a halogen atom; C_1-6alkylaminocarbonyl, optionally substituted by a halogen atom; C_1-6alkylaminocarbonyl, optionally substituted by a halogen atom; C_1-6alkylsulfonate, optionally substituted by a halogen atom; C_1-6alkylthio, optionally substituted by a halogen atom; C_1-6alkylsulfonyl, optionally substituted by a halogen atom; C_1-6alkylsulfonyl, optionally substituted by a halogen atom; cyano; formyl; azide; guanidyl; the group-C(=NH)-NH₂and the group-CH=N-O-CH₃.

Phenyl in "benzoyloxy"represented by R₂, R₃and R₄and R₁₂, R₁₃and R₁₄is optionally substituted, and substituents include halogen atoms; C_1-6alkyloxy, optionally substituted by a halogen atom; C_1-6alkyl, optionally substituted by a halogen atom; C_1-6alkylsulphonyl, optionally substituted by a halogen atom; C_1-6alkylcarboxylic, optionally substituted by halogen atom is; C_1-6alkylcarboxylic, optionally substituted by a halogen atom; C_1-6alkylaminocarbonyl, optionally substituted by a halogen atom; C_1-6alkylaminocarbonyl, optionally substituted by a halogen atom; C_1-6alkylsulfonate, optionally substituted by a halogen atom; C_1-6alkylthio, optionally substituted by a halogen atom; C_1-6alkylsulfonyl, optionally substituted by a halogen atom; C_1-6alkylsulfonyl, optionally substituted by a halogen atom; cyano; nitro; formyl; azide; guanidyl; the group-C(=NH)-NH₂and the group-CH=N-O-CH₃. Preferred are halogen atoms, C_1-6alkyl substituted by halogen atom, cyano and nitro.

Phenyl in "benzosulfimide"represented by R₃and R₄and R₁₃and R₁₄is optionally substituted, and substituents include halogen atoms; C_1-6alkyloxy, optionally substituted by a halogen atom; C_1-6alkyl, optionally substituted by a halogen atom; C_1-6alkylsulphonyl, optionally substituted by a halogen atom; C_1-6alkylcarboxylic, optionally substituted by a halogen atom; C_1-6alkylcarboxylic, optionally substituted by a halogen atom; C_1-6alkylaminocarbonyl, optionally substituted by a halogen atom; C_1-6alkylaminocarbonyl, optional replacement of the military halogen atom; C_1-6alkylsulfonate, optionally substituted by a halogen atom; C_1-6alkylthio, optionally substituted by a halogen atom; C_1-6alkylsulfonyl, optionally substituted by a halogen atom; C_1-6alkylsulfonyl, optionally substituted by a halogen atom; cyano; formyl; azide; guanidyl; the group-C(=NH)-NH₂and the group-CH=N-O-CH₃.

"C_1-6alkylsulfonate"represented by R₂, R₃and R_4,and R₁₂, R₁₃and R₁₄is optionally substituted, and substituents include halogen atoms, cyano, phenyl, triptoreline, triptoreline.

"C_1-6allyloxycarbonyl"represented by R₄and R₁₄is optionally substituted, and substituents include halogen atoms, cyano, phenyl, triptoreline, triptoreline.

"C_1-6alkylaminocarbonyl"represented by R₄and R₁₄is optionally substituted, and substituents include halogen atoms, cyano, phenyl, triptoreline, triptoreline.

"Phenyl"represented by R₂' and R₃'and R₁₂' and R₁₃'and phenyl in "benzyl"represented by R₂' and R₃'and R₁₂' and R₁₃'is optionally substituted, and substituents include halogen atoms, C_1-4alkyl, C_1-4alkyloxy, nitro, cyano, formyl, triptoreline, acetyl, atomic charges.

"Feast upon the TES or unsaturated five - or six-membered heterocyclic ring" in the "saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate", presents R₃and R₁₃and "saturated or unsaturated five - or six-membered heterocyclic oxy", "saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy" and "saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate"represented by R₄and R₁₄preferably is a saturated or unsaturated five - or six-membered heterocyclic ring containing one to three heteroatoms selected from the group comprising atoms of nitrogen, oxygen and sulfur, more preferably a saturated or unsaturated five - or six-membered heterocyclic ring containing one or two heteroatoms selected from the group comprising atoms of nitrogen, oxygen and sulfur, more preferably a saturated or unsaturated five - or six-membered heterocyclic ring containing one or two nitrogen atom, a saturated or unsaturated five - or six-membered heterocyclic ring containing one or two oxygen atom, a saturated or unsaturated five - or six-membered heterocyclic ring containing one or two sulfur atom, a saturated or unsaturated five - or six-membered heterocyclic ring containing one nitrogen atom and one oxygen atom, or a saturated or unsaturated five - or six-membered, heterocy the symbolic ring, containing one nitrogen atom and one sulfur atom.

More specifically, examples of the "saturated or unsaturated five - or six-membered heterocyclic ring" include thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, isothiazolin, isoxazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydropyranyl, piperidinyl, piperazinil, morpholinyl and mannosyl. Preferred are pyridyl, furanyl, thiazolyl, imidazolyl, tetrahydropyranyl and mannosyl. More specifically, these examples include the

(2 - or 3-)thienyl, (2 - or 3-)furyl, (1-, 2 - or 3-)pyrrolyl,

(1-, 2-, 4 - or 5-)imidazolyl, (1-, 3-, 4 - or 5-)pyrazolyl,

(3-, 4 - or 5-)isothiazole, (3-, 4 - or 5-)isoxazolyl,

(2-, 4 - or 5-)thiazolyl, (2-, 4 - or 5-)oxazolyl,

(2-, 3 - or 4-)pyridyl or 2-, 4-, 5 -, or 6-)pyrimidinyl,

(2 - or 3-)pyrazinyl, (3 - or 4-)pyridazinyl,

(2-, 3 - or 4-)tetrahydropyranyl,

(1-, 2-, 3 - or 4-)piperidinyl, (1-, 2 - or 3-)piperazinil and

(2-, 3 - or 4-)morpholinyl, preferably 3-pyridyl, 2-furanyl, 5-thiazolyl, 1-imidazolyl, 5-imidazolyl and 2-tetrahydropyranyl, even more preferably 2-tetrahydropyranyl, 2-pyrazinyl and 3-pyridyl, particularly preferably 3-pyridyl.

Heterocyclic ring in the "saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy" and "saturated or unsaturated five - or six-membered ring of heteros clickcom thiocarbonate", and thieno[3,2-b]pyridylcarbonyl and 1H-indolinecarboxylic"represented by R₄and R₁₄is optionally substituted, and substituents include halogen atoms, C_1-4alkyl, C_1-4alkyloxy, C_1-4alkylthio, nitro, cyano, formyl, triptoreline, trifluoromethyl, triptoreline, triptorelin, trifloromethyl, acetyl, atomic charges, benzoyl and C_1-4allyloxycarbonyl. Preferred are halogen atoms, C_1-4alkyl, C_1-4alkyloxy and trifluoromethyl.

Heterocyclic ring in the "saturated or unsaturated five - or six-membered heterocyclic hydroxy is optionally substituted, and substituents include hydroxyl, benzyloxy, halogen atom, a C_1-4alkyl, C_1-4alkyloxy, nitro, cyano, formyl, triptoreline, trifluoromethyl, triptoreline, triptorelin, trifloromethyl, acetyl, atomic charges. Preferred are hydroxyl and benzyloxy.

The composition for use as a means of pest control, containing the compound represented by formula (I)

According to a preferred variant implementation of the present invention, in the compound represented by formula (I), Het₁preferably means 3-pyridyl.

Further, according to a preferred variant implementation of the ia of the present invention, in the compound represented by formula (I), R₁means hydroxyl, C_1-6alkylcarboxylic, C_1-3alkyloxy or benzyloxy, or oxo in the absence of an atom at position 13, or the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5. More preferably, R₁means hydroxyl or C_1-6alkylcarboxylic, or the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5, even more preferably R₁means hydroxyl.

According to a preferred variant implementation of the present invention, in the compound represented by formula (I), R₂means hydroxyl, optionally substituted C_1-18alkylcarboxylic, optionally substituted benzoyloxy, or C_1-3alkylsulfonate, more preferably optionally substituted C_1-18alkylcarboxylic, even more preferably linear or branched C_1-6alkylcarboxylic (in particular, propionyloxy) or optionally substituted cyclic C_3-6alkylcarboxylic.

In accordance with a preferred embodiment of the present invention, in the compound represented by formula (I), R₃means a hydrogen atom, hydroxyl, optionally Zam is on C _1-18alkylcarboxylic, optionally substituted benzoyloxy, C_1-6alkylsulfonate, optionally substituted, benzosulfimide or saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate, more preferably optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, even more preferably, optionally substituted C_1-6alkylcarboxylic, even more preferably linear or branched C_2-4alkylcarboxylic (in particular, propionyloxy) or optionally substituted cyclic C_3-6alkylcarboxylic.

According to a preferred variant implementation of the present invention, in the compound represented by formula (I), R₂and R₃together denote-O-CR₂'R₃'-O-, where R₂' and R₃'which may be identical or different, represent a hydrogen atom, a C_1-6alkyl, C_1-3alkyloxy, C_2-3alkenyl, benzyl or optionally substituted phenyl, or R₂' and R₃' together denote oxo or C_2-6alkylen. More preferably, R₂and R₃together denote-O-CR₂'R₃'-O-, where R₂' and R₃'which may be identical or different, represent a hydrogen atom, a C_1-6alkyl or optionally substituted phenyl, or Rsub> 2' and R₃' together denote oxo or C_2-6alkylen.

According to a preferred variant implementation of the present invention, in the compound represented by formula (I), R₄means a hydrogen atom, hydroxyl, optionally substituted C_1-18alkylcarboxylic, C_2-6alkenylboronic, C_2-6alkylcarboxylic, C_1-6alkylsulfonate, benzosulfimide, benzyloxy, C_1-3alkyloxy, C_1-3alkyloxy-C_1-3alkyloxy, C_1-3alkylthio-C_1-3alkyloxy, C_1-3alkyloxy-C_1-3alkyloxy-C_1-3alkyloxy, optionally substituted C_1-3allyloxycarbonyl, optionally substituted C_1-6alkylaminocarbonyl, optionally substituted benzoyloxy, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, optionally substituted thieno[3,2-b]pyridylcarbonyl, optionally substituted 1H-indolinecarboxylic or saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate, or oxo in the absence of a hydrogen atom in position 7. More preferably, R₄means hydroxyl, optionally substituted C_1-6alkylcarboxylic, saturated or unsaturated five - resisti-membered heterocyclic oxy, optionally substituted benzoyloxy, C_1-3alkyloxy-C_1-3alkyloxy, optionally substituted C_1-6alkylaminocarbonyl, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, optionally substituted thieno[3,2-b]pyridylcarbonyl, optionally substituted 1H-indolinecarboxylic or saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate, or oxo in the absence of a hydrogen atom in position 7. Even more preferably, R₄means hydroxyl, optionally substituted C_1-6alkylcarboxylic, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted benzoyloxy, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy or saturated or unsaturated five - or six-membered heterocyclic, thiocarbanilide. Even more preferably, R₄means hydroxyl, linear or branched C_2-4alkylcarboxylic (in particular, propionyloxy), optionally substituted cyclic C_3-6alkylcarboxylic or optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy.

According to another preferred variant of the westline of the present invention, in the compound represented by formula (I), Het₁mean 3-pyridyl, R₁means hydroxyl or C_1-6alkylcarboxylic, or the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5, R₂means optionally substituted C_1-6alkylcarboxylic, R₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, or R₂and R₃together represent-O-CR₂'R₃'-O-, where R₂' and R₃'which may be identical or different, denote a hydrogen atom, a C_1-6alkyl or optionally substituted phenyl, or R₂' and R₃' together represent oxo, or C_2-6alkylene, and R₄means hydroxyl, optionally substituted C_1-6alkylcarboxylic, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted benzoyloxy, C_1-3alkyloxy-C_1-3alkyloxy, optionally substituted C_1-6alkylaminocarbonyl, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, optionally substituted thieno[3,2-b]pyridylcarbonyl, optionally substituted 1H-indolinecarboxylic, saturated or unsaturated five - or six-clenn the th heterocyclic, thiocarbonate, or oxo in the absence of a hydrogen atom in position 7.

According to another preferred variant implementation of the present invention, in the compound represented by formula (I), Het₁mean 3-pyridyl, R₁means hydroxyl, R₂means optionally substituted C_1-6alkylcarboxylic and R₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, and R₄means hydroxyl, optionally substituted C_1-6alkylcarboxylic, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted benzoyloxy, C_1-3alkyloxy-C_1-3alkyloxy, optionally substituted C_1-6alkylaminocarbonyl, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, optionally substituted thieno[3,2-b]pyridylcarbonyl, optionally substituted 1H-indolinecarboxylic, saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate, or oxo in the absence of a hydrogen atom in position 7.

According to another preferred variant implementation of the present invention, in the compound represented by formula (I), Het₁mean 3-pyridyl, R₁means hydroxyl, R₂means the optional Sames the config C _1-6alkylcarboxylic, R₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate and R₄means hydroxyl, optionally substituted C_1-6alkylcarboxylic, optionally substituted benzoyloxy, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, or saturated or unsaturated five - or six-membered heterocyclic, thiocarbanilide.

According to another preferred variant implementation of the present invention, in the compound represented by formula (I), Het₁mean 3-pyridyl, R₁means hydroxyl, and R₂and R₃represent an optionally substituted cyclic C_3-6alkylcarboxylic.

According to another preferred variant implementation of the present invention, in the compound represented by formula (I),

Het₁mean 3-pyridyl,

R₁means hydroxyl or

optionally substituted C_1-6alkylcarboxylic, or

the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5,

R₂means optionally substituted C_1-18alkylcarboxylic or obazatelno substituted benzoyloxy,

R₃means optionally substituted C_1-18alkylcarboxylic or optionally substituted C_1-6alkylsulfonate, and

R₄means hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted benzoyloxy,

optionally substituted C_1-6alkylaminocarbonyl,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic oxy,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy,

optionally substituted thieno[3,2-b]pyridylcarbonyl,

optionally substituted 1H-indolinecarboxylic or

oxo in the absence of a hydrogen atom in position 7.

According to another preferred variant implementation of the present invention, in the compound represented by formula (I),

Het₁mean 3-pyridyl,

R₁means hydroxyl or

optionally substituted C_1-6alkylcarboxylic, or

the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5,

R₂means optionally substituted C_1-18alkylcarboxylic,

R₃means optional replacement of the military C _1-18alkylcarboxylic or optionally substituted C_1-6alkylsulfonate, and

R₄means hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted benzoyloxy,

optionally substituted C_1-6alkylaminocarbonyl,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic oxy,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, or

oxo in the absence of a hydrogen atom in position 7.

According to another preferred variant implementation of the present invention, in the compound represented by formula (I),

Het₁mean 3-pyridyl,

R₁means hydroxyl or

optionally substituted C_1-6alkylcarboxylic, or

the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5,

R₂means optionally substituted C_1-18alkylcarboxylic,

R₃means optionally substituted C_1-18alkylcarboxylic,

R₄means hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted benzo is lexi,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic oxy,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy.

According to another preferred variant implementation of the present invention, in the compound represented by formula (I), Het₁mean 3-pyridyl, R₁means hydroxyl, R₂means C_1-6alkylcarboxylic and R₃and/or R₄mean C_2-4alkylcarboxylic.

In addition, acceptable from the point of view of the agriculture and horticulture salt compounds represented by the formula (I), similar salts of the compounds represented by formula (Ib), as described below.

Composition for use as a means of combating bugs pest control, containing the compound represented by formula (Ia)

According to a preferred variant implementation of the present invention, in the compound represented by formula (Ia), Het₂preferably means 3-pyridyl.

In addition, according to a preferred variant implementation of the present invention, in the compound represented by formula (Ia), R₁₁means hydroxyl, C_1-6alkylcarboxylic, C_1-3alkyloxy or benzyloxy, or oxo, otsutstviyem hydrogen in position 13, or the relationship between position 5 and position 13 represents a double bond in the absence of R₁₁and the hydrogen atom in position 5. More preferably, R₁₁means hydroxyl or C_1-6alkylcarboxylic, or the relationship between position 5 and position 13 represents a double bond in the absence of R₁₁and the hydrogen atom in position 5, even more preferably R₁₁means hydroxyl.

According to a preferred variant implementation of the present invention, in the compound represented by formula (Ia), R₁₂means hydroxyl, optionally substituted C_1-18alkylcarboxylic, optionally substituted benzoyloxy, or C_1-3alkylsulfonate, more preferably optionally substituted C_1-18alkylcarboxylic, even more preferably optionally substituted C_1-6alkylcarboxylic, even more preferably linear or branched C_1-6alkylcarboxylic (in particular, propionyloxy) or optionally substituted cyclic C_3-6alkylcarboxylic.

In a preferred embodiment of the present invention, in the compound represented by formula (Ia), R₁₃means a hydrogen atom, hydroxyl, optionally substituted C_1-6alkylcarboxylic, optionally substituted benzoyloxy, C_1-6alkylsulfonate, obazatelno replaced benzosulfimide or saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate, more preferably optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, even more preferably optionally substituted C_1-6alkylcarboxylic, even more preferably linear or branched C_2-4alkylcarboxylic (in particular, propionyloxy) or optionally substituted cyclic C_3-6alkylcarboxylic.

According to a preferred variant implementation of the present invention, in the compound represented by formula (Ia), R₁₂and R₁₃together represent-O-CR₁₂'R₁₃'-O-, where R₁₂' and R₁₃'which may be identical or different, denote hydrogen atoms, C_1-6alkyl, C_1-3alkyloxy, C_2-3alkenyl, benzyl or optionally substituted phenyl, or R₁₂' and R₁₃' together represent oxo, or C_2-6alkylen. More preferably, R₁₂and R₁₃together represent-O-CR₁₂'R₁₃'-O-, where R₁₂' and R₁₃'which may be identical or different, denote hydrogen atoms, C_1-6alkyl or optionally substituted phenyl, or R₁₂' and R₁₃' together represent oxo, or C_2-6alkylen.

According to a preferred variant implementation of the present invention, in the compound represented by formula (Ia), R₁₄means and the om hydrogen, hydroxyl, optionally substituted C_1-18alkylcarboxylic, C_2-6alkenylboronic, C_2-6alkylcarboxylic, C_1-6alkylsulfonate, benzosulfimide, benzyloxy, C_1-3alkyloxy, C_1-3alkyloxy-C_1-3alkyloxy, C_1-3alkylthio-C_1-3alkyloxy, C_1-3alkyloxy-C_1-3alkyloxy-C_1-3alkyloxy, optionally substituted C_1-3allyloxycarbonyl, optionally substituted C_1-6alkylaminocarbonyl, optionally substituted benzoyloxy, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, optionally substituted thieno[3,2-b]pyridylcarbonyl, optionally substituted 1H-indolinecarboxylic, or saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate, or oxo in the absence of a hydrogen atom in position 7. More preferably, R₁₄means hydroxyl, optionally substituted C_1-6alkylcarboxylic, optionally substituted benzoyloxy, saturated or unsaturated five - or six-membered heterocyclic hydroxy, C_1-3alkyloxy-C_1-3alkyloxy, optionally substituted C_1-6alkylaminocarbonyl, optionally substituted nassen the th or unsaturated five - or six-membered heterocyclic, carbonyloxy, optionally substituted thieno[3,2-b]pyridylcarbonyl, optionally substituted 1H-indolinecarboxylic, or saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate, or oxo in the absence of a hydrogen atom in position 7. Even more preferably, R₁₄means hydroxyl, optionally substituted C_1-6alkylcarboxylic, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted benzoyloxy, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, or saturated or unsaturated five - or six-membered heterocyclic, thiocarbanilide. Even more preferably, R₁₄means even more preferably linear or branched C_2-4alkylcarboxylic (in particular, propionyloxy), optionally substituted cyclic C_3-6alkylcarboxylic or optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy.

According to another preferred variant implementation of the present invention, in the compound represented by formula (Ia), Het₂mean 3-pyridyl, R₁₁means hydroxyl or C_1-6alkylcarboxylic, or the relationship between position 5 and position 13 represents voynow relationship in the absence of R ₁₁and the hydrogen atom in position 5, R₁₂means optionally substituted C_1-6alkylcarboxylic, R₁₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, or R₁₂and R₁₃together represent-O-CR₁₂'R₁₃'-O-, where R₁₂' and R₁₃'which may be identical or different, denote hydrogen atoms, C_1-6alkyl or optionally substituted phenyl, or R₁₂' and R₁₃' together represent oxo, or C_2-6alkylene, and R₁₄means hydroxyl, optionally substituted C_1-6alkylcarboxylic, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted benzoyloxy, C_1-3alkyloxy-C_1-3alkyloxy, optionally substituted C_1-6alkylaminocarbonyl, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, optionally substituted thieno[3,2-b]pyridylcarbonyl, optionally substituted 1H-indolinecarboxylic, saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate, or oxo in the absence of a hydrogen atom in position 7.

According to another preferred variant implementation of the present invention, in the compound represented by formula (Ia), Het₂mean 3-pyridyl, R₁₁means hydroxyl, R₁₂means optionally substituted C_1-6alkylcarboxylic and R₁₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, and R₁₄means hydroxyl, optionally substituted C_1-6alkylcarboxylic, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted benzoyloxy, C_1-3alkyloxy-C_1-3alkyloxy, optionally substituted C_1-6alkylaminocarbonyl, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, optionally substituted thieno[3,2-b]pyridylcarbonyl, optionally substituted 1H-indolinecarboxylic, saturated or unsaturated five - or six-membered heterocyclic, thiocarbonate, or oxo in the absence of a hydrogen atom in position 7.

According to another preferred variant implementation of the present invention, in the compound represented by formula (Ia), Het₂mean 3-pyridyl, R₁₁means hydroxyl, R₁₂means optionally substituted C_1-6alkylcarboxylic, R₁₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, and R₁₄means hydroxyl, neoba is consequently substituted C _1-6alkylcarboxylic, optionally substituted benzoyloxy, saturated or unsaturated five - or six-membered heterocyclic oxy, optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, or saturated or unsaturated five - or six-membered heterocyclic, thiocarbanilide.

According to another preferred variant implementation of the present invention, in the compound represented by formula (Ia), Het₂mean 3-pyridyl, R₁₁means hydroxyl, and R₁₂and R₁₃represent an optionally substituted cyclic C_3-6alkylcarboxylic.

According to another preferred variant implementation of the present invention, in the compound represented by formula (Ia),

Het₂mean 3-pyridyl,

R₁₁means hydroxyl or

optionally substituted C_1-6alkylcarboxylic, or

the relationship between position 5 and position 13 represents a double bond in the absence of R₁₁and the hydrogen atom in position 5,

R₁₂means optionally substituted C_1-18alkylcarboxylic

or optionally substituted benzoyloxy,

R₁₃means optionally substituted C_1-18alkylcarboxylic

or optionally substituted C_1-6alkylsulfonate and

R₁₄means hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted benzoyloxy,

optionally substituted C_1-6alkylaminocarbonyl,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic oxy,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy,

optionally substituted thieno[3,2-b]pyridylcarbonyl,

optionally substituted 1H-indolinecarboxylic or

oxo in the absence of a hydrogen atom in position 7.

According to another preferred variant implementation of the present invention, in the compound represented by formula (Ia),

Het₂mean 3-pyridyl,

R₁₁means hydroxyl or

optionally substituted C_1-6alkylcarboxylic, or

the relationship between position 5 and position 13 represents a double bond in the absence of R₁₁and the hydrogen atom in position 5,

R₁₂means optionally substituted C_1-18alkylcarboxylic,

R₁₃means optionally substituted C_1-18alkylcarboxylic

or optionally substituted C_1-6alkylsulfonate and

R₁₄means hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted benzoyloxy,

optionally substituted C_1-6alkylaminocarbonyl,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic oxy,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy, or

oxo in the absence of a hydrogen atom in position 7.

According to another preferred variant implementation of the present invention, in the compound represented by formula (Ia),

Het₂mean 3-pyridyl,

R₁₁means hydroxyl or

optionally substituted C_1-6alkylcarboxylic, or

the relationship between position 5 and position 13 represents a double bond in the absence of R₁₁and the hydrogen atom in position 5,

R₁₂means optionally substituted C_1-18alkylcarboxylic,

R₁₃means optionally substituted C_1-18alkylcarboxylic,

R₁₄means hydroxyl,

optionally substituted C_1-18alkylcarboxylic,

optionally substituted benzoyloxy,

optionally substituted saturated or unsaturated five - or six-membered heterocyclic oxy, or

According to another preferred variant implementation of the present invention, in the compound represented by formula (Ia), Het₂mean 3-pyridyl, R₁₁means hydroxyl, R₁₂means C_1-6alkylcarboxylic and R₁₃and/or R₁₄represents a C_2-4alkylcarboxylic.

In addition, acceptable from the point of view of the agriculture and horticulture salt compounds represented by the formula (Ia), similar salts of the compounds represented by formula (Ib), as described below.

The compounds of formula (Ib) or equivalent acceptable from the point of view of the agriculture and horticulture salt

The compounds of formula (Ib) are new derivatives of peripherin, which are part of the connection represented by the formula (I). In particular, these compounds have significant insecticidal activity.

According to a variant implementation of the present invention represented by the compounds of formula (Ib), excluding the connection, where Het₁mean 3-pyridyl, R₁means hydroxyl, and R₂and R₃represent propionyloxy, and R₄means hydroxyl.

According to another preferred variant implementation of this izopet the tion, in the compound represented by formula (Ib), R₂and R₃represent an optionally substituted cyclic C_3-6alkylcarboxylic, R₄means hydroxyl, optionally substituted cyclic C_3-6alkylcarboxylic or optionally substituted benzoyloxy. Alternative, R₂and R₃represent propionyloxy, R₄means optionally substituted cyclic C_3-6alkylcarboxylic or optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy.

According to another preferred variant implementation of the present invention, in the compounds represented by formula (Ib), R₂and R₃represent an optionally substituted cyclic C_3-6alkylcarboxylic, R₄means hydroxyl, optionally substituted cyclic C_3-6alkylcarboxylic or optionally substituted benzoyloxy.

According to another preferred variant implementation of the present invention, in the compounds represented by formula (Ib), R₂and R₃represent propionyloxy, R₄means optionally substituted cyclic C_3-6alkylcarboxylic or optionally substituted saturated or unsaturated five - or six-membered heterocyclic is carbonyloxy.

According to another preferred variant implementation of the present invention developed a composition for use as a means of pest control, containing the compound represented by formula (Ib), or acceptable from the point of view of the agriculture and horticulture salt of the compounds, as the active ingredient and acceptable from the point of view of the agriculture and horticulture media.

Acceptable from the point of view of the agriculture and horticulture salts of compounds of formula (Ib) include, for example, acid additive salts such as hydrochloride, nitrates, sulfates, phosphates or acetates.

Specific examples of compounds represented by formula (I), (Ia) or (Ib)include compounds shown below in tables 1-14. In the following tables

H(=) means that the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5.

The way to obtain

The composition according to the present invention can be obtained by mixing the compound represented by formula (I), (Ia) or (Ib), as the active ingredient, with acceptable from the point of view of the agriculture and horticulture carrier. The compound represented by formula (I), (Ia) or (Ib), according to the present invention can be obtained by the following method.

From among the compounds of the present invention, compounds represented by formula (II)can be synthesized according to the method described in patent application laid Japan No. 259569/1996 laid patent application of Japan No. 269062/1996 laid patent application of Japan No. 269065/1996 or Journal of Antibiotics (1997), 50(3), pp. 229-36. When peripherin A used as an initial matter, peripherin A, obtained by the method described in Journal of Society of Synthetic Organic Chemistry, Japan (1998), Vol. 56, No. 6, pp. 478-488 or WO94/09417, can be used as the starting material.

[Chemical formula 4]

where

R₁means hydroxyl,

optionally substituted C_1-6alkylcarboxylic,

optionally substituted C_2-6alkenylboronic,

optionally substituted C_2-6alkylcarboxylic,

optionally substituted C_1-6alkyloxy,

optionally substituted C_2-6alkenylacyl,

optionally substituted C_2-6alkyloxy,

optionally substituted benzyloxy or

oxo in the absence of a hydrogen atom in position 13, and

R₂, R₃and R₄have the meanings specified for formula (I).

Next, from among the compounds of the present invention, compounds represented by formula (III)can be synthesized according to the method described in patent application laid Japan No. 269063/1996 or tiled patent application of Japan No. 269066/1996.

[Chemical formula 5]

where R₂, R₃and R₄are as indicated in formula (I).

Application

Insect species against which it is derived peripherin formula (I) or (Ib) of the present invention have a controlling effect include lepidopteran pests, such as, for example: Egyptian cotton bollworm Spodoptera litura, noctuid moth Mamestra brassicae, Pseudaletia separata, green caterpillar, cabbage moth Plutella xylostella, scoop a small Spodoptera exigua, Ognevka Asian Chilo stem suppresalis, Cnaphalocrocis medinalis, leafroller, carposinidae, leaf moth, wananchi, pests belonging to the family of Agrotis spp., agricultural pests belonging to the family of Helicoverpa spp., and agricultural pests belonging to the family of Heliothis spp.; Hemiptera pests, such as, for example, Aphidoidea, including avidity, Hermes and phylloxera, such as aphid greenhouse Myzus persicae, aphids bocheva Aphis gossypii, aphids beet Aphis fabae, Aphis maidis (aphid corn leaf), pea aphid Acyrthosiphon pisum, potato aphid ordinary Aulacorthum solani, alfalfa aphid Aphis craccivora, potato aphid large Macrosiphum euphorbiae, large aphid cereal Macrosiphum avenae, aphids Rosanna-grass Metopolophium dirhodum, bird-cherry aphid ordinary Rhopalosiphum padi aphids cereal ordinary Schizaphis graminum, cabbage aphid Brevicoryne brassicae, mustard aphid sheet Lipaphis erysimi, aphids Tamagawa Aphis citricola, Apple aphid rosy Rosy apple aphid, aphid blood Eriosoma lanigerum, aphid orange Toxoptera aurantii and citrus aphid Toxoptera citricidus; Deltocephalidae) such as Nephotettix cincticeps, delbaldo, such as Laodelphax striatellus, Nilaparvata lugens and Sogatella furcifera; defenders, such as Eysarcoris ventralis, Nezara viridula and Trigonotylus coelestialium; aleyrodidae Aleyrodidae, such as the whitefly Bemisia argentifolii, Bemisia tabaci and Trialeurodes vaporariorum; insects Diaspididae, giant scale, pallet scale, Aclerdiae, Kostyleva aphid Dactylopidae, Kerridae, Volosnikov Pseudococcidae, Coccidae, Eriococcidae, parnozhelezistyh scale Asterolecaniidae, Beesonidae, Lecanodiaspididae or Cerococcidae, such as the Comstock mealybug Pseudococcus comstocki and mealybug grape powdery Planococcus citri Risso; Coleoptera pests, such as, for example, the rice weevil water Lissorhoptrus oryzophilus, Callosobruchuys chienensis, khruschak flour large Tenebrio molitor, Diabrotica virgifera, beetle blaska odinnadtsatietazhnoe Diabrotica undecimpunctata howardi, Anomala cuprea, Anomala rufocuprea, beetle blaska striped Phyllotreta striolata, Aulacophora femoralis, Colorado potato beetle Leptinotarsa decemlineata, Oulema oryzae, Carposinidae and beetles beetles Cerambycidae; the mites Acari, for example, Tetranychus urticae, Tetranychus kanzawai and Panonychus citri; Hymenoptera agricultural pests, such as, for example, real sawyers Tenthredinidae; Orthoptera agricultural pests, such as, for example, real Acrididae grasshoppers; Diptera pests, such as, for example, Muscidae flies and leaf-mining flies Agromyzidae; of Puzanova Thysanopteran pests, such as thrips Thrips palmi and Frankliniella occidentalis; parasitic on plants nematodes Plant Parasitic Nematodes, for example, Meloidogyne hapla, Pratylenchus spp., Aphelenchoides besseyi and Bursaphelenchus xylophilus; and parasites of animals, such as, for example, Siphonaptera fleas, lice, Anoplura, ticks such as Boophilus microplus, Haemaphysalis longicornis, Rhipicephalus sanguineus and Scarcoptes scabiei. Preferred are the bugs of the agricultural pests.

The compound represented by formula (Ia) according to the present invention has a significant regulatory action against Hemiptera pests. Preferred Hemiptera pests are selected from the group including Aphidoidea, such as avidity Aphididae, Hermes Adelgidae and phylloxera Phylloxeridae, particularly preferred are avidity Aphididae; Coccoidea, such as the scale Diaspididae, giant bugs, Margarodidae, plate bugs, Ortheziidae, Aclerdiae, plate scale insects present Kostyleva aphid Dactylopiidae, Kerridae, walochnik Pseudococcidae, Coccidae, Eriococcidae, parnozhelezistyh bugs, Asterolecaniidae, Beesonidae, Lecanodiaspididae and Cerococcidae; and aleyrodidae Aleyrodidae. More preferred are a aphid greenhouse Myzus persicae, aphids bocheva Aphis gossypii, aphids beet Aphis fabae, Aphis maidis (aphid corn leaf), pea aphid Acyrthosiphon pisum, potato aphid ordinary Aulacorthum solani, alfalfa aphid Aphis craccivora, potato aphid large Macrosiphum euphorbiae, large aphid cereal Macrosiphum avenae, aphids Rosanna-grass Metopolophium dirhodum, bird-cherry aphid ordinary Rhopalosiphum padi aphids cereal ordinary Schizaphis graminum, cabbage aphid Brevicoryne brassicae, mustard aphid sheet Lipaphis erysimi, aphids Tamagawa Aphis citricola, Apple aphid rosy Rosy apple aphid, aphid blood Eriosoma lanigerum, aphid orange Toxoptera aurantii, citrus aphid Toxoptera citricidus and the Comstock mealybug Pseudococcus costocki.

The composition according to the present invention can be presented in the form of any suitable composition, such as emulsifiable concentrates, liquid formulations, suspensions, wettable powder, flowable substances, dust, granules, tablets, oil solutions, aerosols or means for fumigation, using acceptable from the point of view of the agriculture and horticulture media. Thus, the carriers include solid carriers, liquid carriers, gaseous carriers, surfactants, dispersing funds and/or other adjuvants for trains and the like.

Used in the present invention the solid carriers include, for example, substances such as talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon black and calcium carbonate.

Examples of liquid carriers include alcohols such as methanol, n-hexanol and ethylene glycol; ketones, such as acetone, methyl ethyl ketone and cyclohexanone; aliphatic hydrocarbons such as n-hexane, kerosene and light oil; aromatic hydrocarbons, such as toluene, xylene and methylnaphthalene; ethers, such as diethyl ether, dioxane and tetrahydrofuran; esters such as ethyl acetate; NITRILES, such as acetonitrile and isobutyronitrile; acid amides such as dimethylformamide and dimethylacetamide; vegetable oils, such is as soybean oil and cottonseed oil; dimethyl sulfoxide and water.

Gaseous carriers include, for example, LPG, air, nitrogen, carbon dioxide and dimethyl ether.

Surfactants or dispersing means, acceptable to, for example, emulsification, dispersion or distribution include, for example, alkylsulfonate esters, salts of alkyl(aryl)sulfonic acid, polyoxyalkylene(aryl)new esters, esters of polyhydric alcohols and salts of lignosulphonic acid.

Adjuvants used to enhance the performance of the compositions include, for example, substances such as carboxymethylcellulose, gum Arabic, polyethylene glycol and calcium stearate.

The above carriers, surfactants, dispersing means and adjuvants can be used, depending on requirements, either separately or in combination.

The concentration of active ingredient in the composition has no particular restrictions. However, usually the amount of active ingredient is 1-75 mass % for emulsifiable concentrates, 0.3 to 25 mass % for dust, 1-90 mass % for wettable powder and 0.5 to 10 mass % for granules.

The compound represented by formula (I), (Ia), (Ib), or acceptable from the point of view of the agriculture and horticulture salt of the compounds and the above compositions containing these compounds, can is to be applied to plants or soil. In addition, according to another aspect of the present invention, a method of combating agricultural pests, comprising applying an effective amount of the compound represented by formula (I), or acceptable from the point of view of the agriculture and horticulture salts of the compounds on the plant or soil. According to another aspect of the present invention presents a way of dealing with bugs agricultural pests, comprising applying an effective amount of the compound represented by formula (Ia), or acceptable from the point of view of the agriculture and horticulture salts of the compounds on the plant or soil. Further, according to another aspect of the present invention, a method of combating agricultural pests, comprising applying an effective amount of the compound represented by formula (Ib), or acceptable from the point of view of the agriculture and horticulture salts of the compounds on the plant or soil. Preferred methods for applying the compound or composition on plants or soil, including processing distribution over the surface, soil treatment, surface treatment and processing of fumigation.

Processing distribution on the surface include, for example, the spreading, prisciani, the dusting, spraying, application of granular preparations and application by dipping. Soil treatment include, for example, pouring the soil and mixing with soil. Examples of surface treatments include, for example, application layer, deposition of dust and the floor. Processing fumigation include, for example, cover the soil with plastic wrap after soil injection. Therefore, the methods of struggle of the present invention include a method in which the compound represented by formula (I), (Ia) or (Ib), or a composition containing the specified connection, applied by fumigation in a confined space.

The composition according to the present invention can be used in a mixture or in combination, for example, with other insecticides, fungicides, miticide, herbicides, plant growth regulators or fertilizers. Tools that can be mixed or used in combination, include the tools described, for example, in The Pesticide Manual, 13th edition, published by The British Crop Protection Council and SHIBUYA INDEX, the 10th edition, 2005, published by SHIBUYA INDEX RESEARCH GROUP. More specifically, the insecticides used in this case include, for example, organophosphorus ester compounds such as Arafat, dichlorvos, EPN, fenitrothion, fenamiphos, prothiofos, profenofos, pyraclofos, chlorpyrifos and diazinon; urethane compounds such as meth is nice, thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fanatical, pirimicarb, carbofuran and benfuracarb; nereistoxin derivatives, such as cartap and thiocyclam; organochlorine compounds such as dicofol and tetradifon; PYRETHROID compounds such as permethrin, tefluthrin, cypermethrin, deltamethrin, cigalotrin, fenvalerate, fluvalinate, etofenprox and selflove; connection benzoylacetone, such as diflubenzuron, teflubenzuron, flufenoxuron and chlorfluazuron; compounds such juvenile hormone, such as methoprene; and Edison-like compounds such as chromafenozide. Others used in this connection include buprofezin, hexythiazox, amitraz, Chlordimeform, pyridaben, fenpyroximate, pyrimidifen, tebufenpyrad, flociprin, achiezer, titlemedium, flubendiamide, ethiprole, fipronil, etoxazole, Imidacloprid, clothianidin, pymetrozine, bifenazate, spirodiclofen, spiromesifen, flonicamid, chlorfenapyr, pyriproxifen, indoxacarb, pyridalyl or spinosad, ivermectin, milbemycin, ORGANOMETALLIC compounds, dinitro-compounds, organo-sulfur compounds, compounds of urea, triazine compounds, hydrazine powered connection.

The composition according to the present invention can also be used in the form of a mixture or combination with microbial p is sticide, such as BT-compositions and entomopathogenic virus tools.

Used in this description of the fungicides include, for example, strobilurin compounds such as AZOXYSTROBIN, kresoximmethyl and Trifloxystrobin; anilinopyrimidines compounds such as mepanipyrim, Pyrimethanil and cyprodinil; azole compounds such as triadimefon, bitertanol, triflumizole, itaconate, propiconazol, penconazole, flusilazol, myclobutanil, tsyprokonazolu, tebuconazole, hexaconazole, prochloraz and semiconical; hinoksalinovym compounds such as chinomethionat; connection dithiocarbamate, such as MANEB, zineb, MANCOZEB, polycarbamate and propineb; connection phenylcarbamate, such as dietphenterm; organochlorine compounds such as CHLOROTHALONIL, hintzen; the benzimidazole compounds, such as benomyl, thiophanate and carbendazim; connection phenylamide, such as metalaxyl, oxadixyl, furac, benalaxyl, parallaxes and zeroforum; join sultanovoy acid, such as dichlofluanid; copper compounds such as copper hydroxide and copper-oxen; connection isoxazol such as hydroxyethoxy; organophosphorus compounds such as postillonne and cyclophosphates; N-halogenoalkane compounds such as Captan, captafol and folpet; dicarboximide compounds such as procymidone, iprodione and wingl the Zolin; benzanilide compounds such as flutolanil and mepronil; morpholine compounds such as fenpropimorph and dimethomorph; ORGANOTIN compounds, such as fistinginaction and fantinato; and cyanopyrrolidine compounds such as fludyoksonil and fenpiclonil. Others used in this connection include ftale, fluazinam, having cymoxanil, triforine, pirivenas, fenarimol, fenpropidin, pencycuron, cyazofamid, iprovalicarb and benthiavalicarb, and the like.

According to another aspect of the present invention, discusses the use of compounds represented by formula (I), or acceptable from the point of view of the agriculture and horticulture salts of the compounds as a means of pest control. According to another aspect of the present invention discusses the use of compounds represented by formula (Ia), or acceptable from the point of view of the agriculture and horticulture salts of the compounds as a means of pest control. According to another aspect of the present invention, discusses the use of compounds represented by formula (Ib), or acceptable from the point of view of the agriculture and horticulture salts of the compounds as a means of combating agricultural what reditelyami.

[Examples]

The present invention is illustrated further by the following examples, which are not considered as limiting the invention. The numbers of the compounds correspond to the numbers in tables 1-14.

Example 1: synthesis of compound 73

Compound 76 (890 mg)synthesized by a method described in patent publication laid Japan No. 259569/1996, dissolved in 80% aqueous solution of methanol. Then to the solution was added 1,8-diazabicyclo[5.4.0]undeca-7-ene (216 mg) and the mixture is stirred at room temperature for 1.5 hour. To the reaction mixture add acetic acid to quench the reaction, and the solvent is removed by evaporation under reduced pressure. Add water to precipitate crystals, followed by extraction with chloroform. The chloroform layer is washed with saturated salt solution, dried over anhydrous magnesium sulfate and the solvent is removed by evaporation under reduced pressure, obtaining the crude product of compound 73. The crude product is purified by chromatography on silica gel (Mega Bond Elut (Varian), a mixture of acetone:hexane=1:1)to give compound 73 (451 mg).

Mass spectrometric data (FAB⁺): 570(M+H)⁺

Example 2: Synthesis of compound 218

Compound 102 (30 mg)synthesized by a method described in patent publication laid Japan No. 259569/1996, and cyclopropanecarbonyl acid (112 what g) dissolved in anhydrous N,N-dimethylformamide (2 ml) and to the solution was added the hydrochloride of l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (76 mg) and 4-(dimethylamino)pyridine (32 mg). The reaction solution was stirred at room temperature for 68 hours and then poured into water, followed by extraction with ethyl acetate. An ethyl acetate layer was washed with saturated salt solution, dried over anhydrous magnesium sulfate and the solvent is removed by evaporation under reduced pressure, obtaining the crude product of compound 218. The crude product is purified preparative thin-layer chromatography (Merck Silica Gel 60 F₂₅₄, 0.5 mm, a mixture of acetone:hexane=1:1)to give compound 218 (33 mg).

Mass spectrometric data (FAB⁺): 662(M+H)⁺

Example 3: synthesis of compound 261

Connection 218 (1.07 g)obtained in example 2, is dissolved in 80% aqueous solution of methanol. To the solution was added 1,8-diazabicyclo[5.4.0]undeca-7-ene (271 mg) and the mixture is stirred at room temperature for 24.5 hours. To the reaction mixture add acetic acid to quench the reaction, and the solvent is removed by evaporation under reduced pressure. Add water to precipitate crystals, followed by extraction with chloroform. The chloroform layer is washed with saturated salt solution, dried over anhydrous magnesium sulfate and the solvent is removed by evaporation under reduced pressure, obtaining the crude product of compound 261. The crude product is purified by chromatography on silica gel (Mega Bond Elut (Varian), a mixture of acetone:hexa is=1:1), receiving a connection 261 (233 mg).

Mass spectrometric data (ESI⁺): 594(M+H)⁺

Example 4: synthesis of compound 222

Compound 73 (30 mg)obtained in example 1, and 4-(trifluoromethyl)nicotinic acid (30 mg) was dissolved in anhydrous N,N-dimethylformamide (3 ml). Then to the solution was added the hydrochloride of l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (15 mg) and 4-(dimethylamino)pyridine (4 mg), the reaction solution was stirred at room temperature for 15 h and then poured into water, followed by extraction with ethyl acetate. An ethyl acetate layer was washed with saturated salt solution, dried over anhydrous magnesium sulfate and the solvent is removed by evaporation under reduced pressure, obtaining the crude product of compound 222. The crude product is purified preparative thin-layer chromatography (Merck Silica Gel 60 F₂₅₄, 0.5 mm, a mixture of acetone:hexane=1:1)to give compound 222 (19 mg).

Mass spectrometric data (FAB⁺): 743(M+H)⁺

Example 5: Synthesis of compound 269

Compound 261 (20 mg)obtained in example 3 and 2-cyanobenzoic acid (30 mg) was dissolved in anhydrous N,N-dimethylformamide (1 ml) and to the solution was added the hydrochloride of l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (26 mg) and 4-(dimethylamino)pyridine (4 mg). The reaction solution was stirred at room temperature for 12 hours and add auktsionnyi solution to water, followed by extraction with ethyl acetate. An ethyl acetate layer was washed with saturated salt solution and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation under reduced pressure, obtaining the crude product of compound 269. The crude product is purified preparative thin-layer chromatography (Merck Silica Gel 60 F₂₅₄, 0.5 mm, a mixture of acetone:hexane=1:1)to give compound 269 (18 mg).

Mass spectrometric data (ESI⁺): 723 (M+H)⁺

Example 6: synthesis of compound 225

1,7,11-Trideceth-13-oxo-6-globalpipe A (10 mg)described in Journal of Antibiotics (1997), 50 (3), 229-36, dissolved in anhydrous N,N-dimethylformamide (1 ml). To the solution is added triethylamine (24 mg) and 4-(dimethylamino)pyridine (0.5 mg) and the mixture is stirred at room temperature for 30 minutes Then add the anhydride propionic acid (8 mg). The reaction solution was stirred at the same temperature for 4 hours. The reaction solution was added water and the mixture extracted with ethyl acetate. An ethyl acetate layer was washed with saturated salt solution, dried over anhydrous magnesium sulfate and then the solvent is removed by evaporation under reduced pressure, obtaining the crude product of compound 225. The crude product is purified preparative thin-layer chromatography (Merck Silica Gel 60 F₂₅₄, 0.5 mm, a mixture of acetone:hexane=1:1), obtaining the connection is of 225 (5.6 mg).

Mass spectrometric data (ESI⁺): 658 (M+H)⁺

Example 7: Synthesis of compound 226

Compound 225 (10 mg)obtained in example 6, is dissolved in methanol (1 ml). To the solution add heptahydrate cerium chloride(III) (57 mg) and detribalized (6 mg). The mixture is stirred at 0°C for 7 h and the reaction solution was added water, followed by extraction with ethyl acetate. An ethyl acetate layer was washed with saturated salt solution, dried over anhydrous magnesium sulfate and the solvent is removed by evaporation under reduced pressure, obtaining the crude product of compound 226. The crude product is purified preparative thin-layer chromatography (Merck Silica Gel 60 F₂₅₄, 0.5 mm, a mixture of acetone:hexane=1:1)to give compound 226 (8.5 mg).

Mass spectrometric data (ESI⁺): 660 (M+H)⁺

Example 8: synthesis of compound 273

1,7,11-Trideceth-1,11-o-p-methoxybenzylideneamino A (10 mg)described in patent publication laid Japan No. 269065/1996, dissolved in anhydrous dichloromethane (0.5 ml, and the solution was added pyridinium dichromate (PDC) (39 mg). The reaction solution was stirred at room temperature for 4 hours and the reaction solution is added to the water. The dichloromethane layer was washed with saturated salt solution, dried over anhydrous sodium sulfate and then the solvent is removed by evaporation p and reduced pressure, receiving the crude product of compound 273. The crude product is purified preparative thin-layer chromatography (Merck Silica Gel 60 F₂₅₄, 0.5 mm, a mixture of chloroform:methanol=12,5:1)to give compound 273 (4.4 mg).

Mass spectrometric data (ESI⁺): 574 (M+H)⁺

Example 9: Synthesis of compound 274

1,11-o-Cyclic carbonate-1,7,11-tridecemlineatus A (4 mg)described in a publication published patent application of Japan No. 269065/1996, dissolved in anhydrous dichloromethane (1 ml). To the solution add triethylamine (5 μl) and 4-(dimethylamino)pyridine (1 mg). The reaction solution was stirred at room temperature for 30 min and add anhydride valerianic acid (5 ml). Then the reaction solution was stirred at room temperature for 3 hours. The reaction solution is added to water, the dichloromethane layer was washed with saturated salt solution and dried over anhydrous sodium sulfate. Then the solvent is removed by evaporation under reduced pressure, obtaining the crude product of compound 274. The crude product is purified preparative thin-layer chromatography (Merck Silica Gel 60 F₂₅₄, 0.5 mm, a mixture of chloroform:methanol=25:1)to give compound 274 (0.1 mg).

Mass spectrometric data (ESI⁺): 652 (M+H)⁺

Example 10

The compounds listed in tables 15-17, synthesize, using ex the derivative of the substance, the reaction reagents 1 and 2 and the solvents indicated in the tables. In addition,¹H-NMR data for certain compounds of tables 15-17 are shown in tables 18 and 29. For withdrawal¹H-NMR using CDCl₃as a solvent. When removing the¹H-NMR as a standard substance tetramethylsilane was used.

Example 11

Example 1 drug [Wettable powder]

The above ingredients homogeneous mixed, and the mixture grind, receiving wettable powder.

Example of preparation 2 [Dostum]

The above ingredients homogeneous mix, getting the dust.

The example of the drug 3 [emulsifiable concentrate]

The above ingredients homogeneous mix and dissolve, getting emulsifiable concentrate.

Sample preparation 4 [granules]

The above ingredients homogeneous crushed and homogeneous mix. Add water to the mixture, followed by thorough mixing. Then the kneaded product granularit and dried, obtaining granules.

Sample preparation 5 [fluid matter]

All of the above ingredients, except for the 1% aqueous solution of xanthan gum and an appropriate quantity of water, previously mixed, and the mixture is then ground in the mill for wet grinding. Then milled product was added 1% aqueous solution of xanthan gum and the remaining water, receiving 100 wt.% fluid substances.

The test example 1: pesticide action against aphid greenhouse Myzus persicae

From among the compounds of formula (I)obtained above conventional method, the compounds listed in tables 1-14, and peripherin A research on pesticide dei is a journey.

Leaf disk with a diameter of 2.8 φ cut from cabbage grown in a flower pot, and placed 5.0 cm Schale. Four adult specimens aphid Myzus persicae release Schale. A day after the release of adult adult aphids aphids are removed. The number of larvae of the first age, born in the leaf disk was adjusted to 10 and the test solution, brought to a concentration of 20 ppm by adding 50% aqueous acetone solution (supplemented with 0.05% of Tween 20), cover the cabbage leaf disk. Then cabbage leaf disk dried in air. Then Schale cover with a lid and leave to stand in a temperature-controlled room (light period 16 hour dark period 8 HR) (25°C). Three days after leaving Schale see larvae, studying for survival or death, and the ratio of the death of the larvae calculated by the following equation.

The ratio mortality (%)={number of dead larvae/(the number of surviving larvae+number of dead larvae)}×100

It was established that the death ratio is not less than 80% for compounds№№ 1, 6, 8, 9, 10, 12, 14, 16, 18, 20, 23, 25, 28, 34, 35, 36, 37, 38, 39, 40, 44, 45, 49, 54, 56, 57, 61, 69, 76, 82, 85, 86, 88, 90, 91, 98, 103, 106, 107, 108, 109, 111, 125, 128, 133, 135, 137, 139, 142, 153, 160, 161, 162, 164, 167, 169, 170, 171, 172, 176, 180, 182, 183, 186, 187, 190, 196, 201, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 226, 227, 228, 229, 230, 231, 232, 233, 236, 237, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 25, 266, 267, 268, 269, 270, 271, 272, 273 and 274, and peripherin A.

The test example 2: pesticide action against aphid greenhouse Myzus persicae

From among the compounds of formula (I)obtained above conventional method, the compounds listed in tables 1-14, and peripherin A research on the pesticide action.

Leaf disk with a diameter of 2.8 φ cut from cabbage grown in a flower pot, and placed 5.0 cm Schale. Four adult specimens aphid Myzus persicae release Schale. A day after the release of adult adult aphids aphids are removed. The number of larvae of the first age, born in the leaf disk was adjusted to 10 and the test solution, brought to a concentration of 0,156 ppm by adding 50% aqueous acetone solution (supplemented with 0.05% of Tween 20), cover the cabbage leaf disk. Then cabbage leaf disk dried in air. Then Schale cover with a lid and leave to stand in a temperature-controlled room (light period 16 hour dark period 8 HR) (25°C). Three days after leaving Schale see larvae, studying for survival or death, and the ratio of the death of the larvae expect the same manner as in test example 1.

It was established that the death ratio is not less than 80% for compounds№№ 12, 23, 28, 45, 54, 56, 76, 82, 85, 86, 90, 164, 201, 205, 206, 207, 212, 213, 217, 218, 219, 222, 227, 228, 229, 231, 232, 233, 237, 239, 240, 242, 246, 247, 249, 250, 252 253, 256, 258, 261, 262, 264, 265, 266, 267, 269, 270 and 271.

The test example 3: pesticide action against cabbage moth Plutella xylostella

Cabbage leaf disk with a diameter of 5 cm is placed in a plastic Cup. Compound diluted to the desired concentration by adding 50% aqueous acetone solution (supplemented with 0.05% of Tween 20), cover the cabbage leaf disk with the help of spray guns and then cabbage leaf disk dried in air. Five larvae of Plutella xylostella in the second age release into the Cup. The cap is then covered with a lid and larvae grown in a temperature-controlled room (25°C). Three days after treatment see larvae, studying for survival or death, and the ratio of the death of the larvae expect the same manner as in test example 1.

It was established that the death ratio is not less than 80% for compounds No. 76, 213, 218, 237 and 250 at a concentration of 500 h/million

The test example 4: pesticide action against Helicoverpa armigera

Cabbage leaf disk with a diameter of 2.8 cm was placed in a plastic Cup. Compound diluted to the desired concentration by adding 50% aqueous acetone solution (supplemented with 0.05% of Tween 20), cover the cabbage leaf disk with the help of spray guns, and then cabbage leaf disk dried in air. Larvae of Helicoverpa armiger in the third age stage release into the Cup. The cap is then covered with a lid and larvae grown in a temperature-controlled room (25°C). Three days after treatment see larvae, studying survival or death. The test is repeated 5 times. Then the ratio of the death of the larvae expect the same manner as in test example 1.

It was established that the death ratio is not less than 80% for compound No. 219 at a concentration of 100 h/million

The test example 5: pesticide action against Triaonotylus caelestialium

The seedling of wheat dipped for 30 seconds in a solution in which each test compound diluted to the desired concentration by adding 50% aqueous acetone solution (supplemented with 0.05% of Tween 20). The seedling of wheat air-dried and then placed in a glass cylinder. Then two larvae Trigonotylus caelestialium on the second age release in the glass cylinder. Then glass cylinder covered with a lid, and larvae grown in a temperature-controlled room (25°C). During the test, seedling wheat feed water from the bottom of the glass cylinder. Three days after treatment see larvae, studying for survival or death, and the ratio of the death of the larvae expect the same manner as in test example 1.

It was established that the death ratio is not less than 80% for compounds No. 218, 261 when the concentration is of 100 h/million

1. The composition for use as a means of pest control, containing the compound represented by formula (I), or acceptable from the point of view of the agriculture and horticulture salt of the compounds as the active ingredient and acceptable from the point of view of the agriculture and horticulture media:
[Chemical formula 1]

where Het₁means optionally substituted 3-pyridyl,
R₁means hydroxyl,
optionally substituted C_1-6alkylcarboxylic,
optionally substituted C_1-6alkyloxy, or
oxo in the absence of a hydrogen atom in position 13, or
the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5,
R₂means hydroxyl,
optionally substituted C_1-18alkylcarboxylic,
optionally substituted benzoyloxy, or
optionally substituted C_1-6alkylsulfonate,
R₃means a hydrogen atom,
hydroxyl,
optionally substituted C_1-18alkylcarboxylic,
optionally substituted benzoyloxy,
optionally substituted C_1-6alkylsulfonate,
optionally substituted, benzosulfimide,
optionally substituted, imidazoledicarboxylic, or
R 2and R₃together represent-O-CR₂'R₃'-O-, where R₂' and R₃'which may be identical or different, denote a hydrogen atom, a C_1-6alkyl, C_1-6alkyloxy,_2-6alkenyl, optionally substituted phenyl or optionally substituted benzyl, or R₂' and R₃' together denote oxo or_2-6alkylen, and
R₄means a hydrogen atom,
hydroxyl,
optionally substituted C_1-18alkylcarboxylic,
optionally substituted C_2-6alkenylboronic,
optionally substituted C_2-6alkylcarboxylic,
optionally substituted benzoyloxy,
optionally substituted C_1-6alkylsulfonate,
optionally substituted, benzosulfimide,
optionally substituted benzyloxy,
optionally substituted C_1-6alkyloxy,
With_1-6alkyloxy-C_1-6alkyloxy,
With_1-6alkylthio-C_1-6alkyloxy,
With_1-6alkyloxy-C_1-6alkyloxy-C_1-6alkyloxy,
optionally substituted C_1-6allyloxycarbonyl,
optionally substituted C_1-6alkylaminocarbonyl,
optionally substituted, tetrahydropyranyloxy,
optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy where the specified heterocyclic part of abrana from the group consisting of pyridyl, teinila, thiazolidinedione and imidazolyl,
optionally substituted thieno[3,2-b]pyridylcarbonyl,
optionally substituted 1H-indolinecarboxylic,
optionally substituted, imidazoledicarboxylic, or
oxo in the absence of a hydrogen atom in position 7, provided that the connection where
Het₁mean 3-pyridyl,
R₁means hydroxyl and
each of R₂, R₃and R₄are the atomic charges,
eliminated.

2. The composition according to claim 1,
where Het₁mean 3-pyridyl,
R₁means hydroxyl or C_1-6alkylcarboxylic, or
the relationship between position 5 and position 13 represents a double bond in the absence of R₁and the hydrogen atom in position 5,
R₂means optionally substituted C_1-6alkylcarboxylic,
R₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate or
R₂and R₃together represent-O-CR₂'R₃'-O-, where R₂' and R₃'which may be identical or different, denote a hydrogen atom, a C_1-6alkyl or optionally substituted phenyl, or R₂' and R₃' together represent oxo or_2-6alkylen, and
R₄means hydroxyl,
optionally substituted C_1-6alkylcarboxylic,
optionally substituted, tetrahydropyranyloxy,
optionally substituted benzoyloxy,
With_1-3alkyloxy-C_1-3alkyloxy,
optionally substituted C_1-6alkylaminocarbonyl,
optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy where the specified heterocyclic selected from the group consisting of pyridyl, teinila, thiazolidinedione and imidazolyl,
optionally substituted thieno[3,2-b]pyridylcarbonyl,
optionally substituted 1H-indolinecarboxylic,
optionally substituted, imidazoledicarboxylic, or
oxo in the absence of a hydrogen atom in position 7.

3. The composition according to claim 1,
where Het₁mean 3-pyridyl,
R₁means hydroxyl,
R₂means optionally substituted C_1-6alkylcarboxylic and
R₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, and
R₄means hydroxyl,
optionally substituted C_1-6alkylcarboxylic,
optionally substituted, tetrahydropyranyloxy,
optionally substituted benzoyloxy,
With_1-3alkyloxy-C_1-3alkyloxy,
optionally substituted C_1-6alkylaminocarbonyl,
optionally substituted saturated or unsaturated five - or six-members of the hydrated heterocyclic, carbonyloxy, where specified heterocyclic selected from the group consisting of pyridyl, teinila, thiazolidinedione and imidazolyl,
optionally substituted thieno[3,2-b]pyridylcarbonyl,
optionally substituted 1H-indolinecarboxylic,
optionally substituted, imidazoledicarboxylic, or
oxo in the absence of a hydrogen atom in position 7.

4. The composition according to claim 1,
where Het₁mean 3-pyridyl,
R₁means hydroxyl,
R₂means optionally substituted C_1-6alkylcarboxylic,
R₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate and
R₄means hydroxyl,
optionally substituted C_1-6alkylcarboxylic,
optionally substituted, tetrahydropyranyloxy,
optionally substituted benzoyloxy,
optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy where the specified heterocyclic selected from the group consisting of pyridyl, teinila, thiazolidinedione and imidazolyl, or imidazoledicarboxylic.

5. The composition according to claim 1,
where Het₁mean 3-pyridyl,
R₁means hydroxyl and
R₂and R₃represent an optionally substituted cyclic With_3-6alkylcarboxylic.

6. Composition for the use of the program as a means of combating bugs pest control, containing the compound represented by formula (Ia), or acceptable from the point of view of the agriculture and horticulture salt of the compounds as the active ingredient and acceptable from the point of view of the agriculture and horticulture media:
[Chemical formula 2]

where
Het₂means optionally substituted 3-pyridyl,
R₁₁means hydroxyl,
optionally substituted C_1-6alkylcarboxylic,
optionally substituted C_1-6alkyloxy,
optionally substituted benzyloxy or
oxo in the absence of a hydrogen atom in position 13, or
the relationship between position 5 and position 13 represents a double bond in the absence of R₁₁and the hydrogen atom in position 5,
R₁₂means hydroxyl,
optionally substituted C_1-18alkylcarboxylic,
optionally substituted benzoyloxy, or
optionally substituted C_1-6alkylsulfonate,
R₁₃means a hydrogen atom,
hydroxyl,
optionally substituted C_1-18alkylcarboxylic,
optionally substituted benzoyloxy,
optionally substituted C_1-6alkylsulfonate,
optionally substituted, benzosulfimide or
optionally substituted, imidazoledicarboxylic, or
R₁₂and R₁₃together represent-O-C ₁₂'R₁₃'-O-, where R₁₂' and R₁₃'which may be identical or different, denote a hydrogen atom, a C_1-6alkyl, C_1-6alkyloxy,_2-6alkenyl, optionally substituted phenyl or optionally substituted benzyl, or R₁₂' and R₁₃' together denote oxo or_2-6alkylen, and
R₁₄means a hydrogen atom,
hydroxyl,
optionally substituted C_1-18alkylcarboxylic,
optionally substituted C_2-6alkenylboronic,
optionally substituted C_2-6alkylcarboxylic,
optionally substituted benzoyloxy,
optionally substituted C_1-6alkylsulfonate,
optionally substituted, benzosulfimide,
optionally substituted benzyloxy,
optionally substituted C_1-6alkyloxy,
With_1-6alkyloxy-C_1-6alkyloxy,
With_1-6alkylthio-C_1-6alkyloxy,
With_1-6alkyloxy-C_1-6alkyloxy-C_1-6alkyloxy,
optionally substituted C_1-6allyloxycarbonyl,
optionally substituted C_1-6alkylaminocarbonyl,
optionally substituted, tetrahydropyranyloxy,
optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy where the specified heterocyclic selected from the group consisting of pyridyl, Tien is La, thiazolidinedione and imidazolyl,
optionally substituted thieno[3,2-b]pyridylcarbonyl,
optionally substituted 1H-indolinecarboxylic,
optionally substituted, imidazoledicarboxylic, or
oxo in the absence of a hydrogen atom in position 7.

7. The composition according to claim 6,
where Het₂mean 3-pyridyl,
R₁₁means hydroxyl or C_1-6alkylcarboxylic, or
the relationship between position 5 and position 13 represents a double bond in the absence of R₁₁and the hydrogen atom in position 5,
R₁₂means optionally substituted C_1-6alkylcarboxylic,
R₁₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, or
R₁₂and R₁₃together represent-O-CR₁₂'R₁₃'-O-, where R₁₂' and R₁₃'which may be identical or different, denote a hydrogen atom, a C_1-6alkyl or optionally substituted phenyl, or R₁₂' and R₁₃' together represent oxo or_2-6alkylen, and
R₁₄means hydroxyl,
optionally substituted C_1-6alkylcarboxylic,
tetrahydropyranyloxy,
optionally substituted benzoyloxy,
With_1-3alkyloxy-C_1-3alkyloxy,
optionally substituted C_1-6alkylaminocarbonyl,
optionally substituted feast upon the config or unsaturated five - or six-membered heterocyclic, carbonyloxy, where specified heterocyclic selected from the group consisting of pyridyl, teinila, thiazolidinedione and imidazolyl
optionally substituted thieno[3,2-b]pyridylcarbonyl,
optionally substituted 1H-indolinecarboxylic, imidazoledicarboxylic or oxo in the absence of a hydrogen atom in position 7.

8. The composition according to claim 6,
where Het₂mean 3-pyridyl,
R₁₁means hydroxyl,
R₁₂means optionally substituted C_1-6alkylcarboxylic and
R₁₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, and
R₁₄means hydroxyl,
optionally substituted C_1-6alkylcarboxylic,
tetrahydropyranyloxy,
optionally substituted benzoyloxy,
With_1-3alkyloxy-C_1-3alkyloxy,
optionally substituted C_1-6alkylaminocarbonyl,
optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy where the specified heterocyclic selected from the group consisting of pyridyl, teinila, thiazolidinedione and imidazolyl
optionally substituted thieno[3,2-b]pyridylcarbonyl,
optionally substituted 1H-indolinecarboxylic,
imidazoledicarboxylic, or
oxo in the absence of a hydrogen atom in position 7.

9. Compo is ice according to claim 6,
where Het₂mean 3-pyridyl,
R₁₁means hydroxyl,
R₁₂means optionally substituted C_1-6alkylcarboxylic,
R₁₃means optionally substituted C_1-6alkylcarboxylic or C_1-6alkylsulfonate, and
R₁₄means hydroxyl,
optionally substituted C_1-6alkylcarboxylic,
optionally substituted, tetrahydropyranyloxy,
optionally substituted benzoyloxy,
optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy where the specified heterocyclic selected from the group consisting of pyridyl, teinila, thiazolidinedione and imidazolyl or
imidazoledicarboxylic.

10. The composition according to claim 6,
where Het₂mean 3-pyridyl,
R₁₁means hydroxyl,
R₁₂and R₁₃represent an optionally substituted cyclic With_3-6alkylcarboxylic.

11. The composition according to claim 6, where these bugs pests are selected from the group including Aphidoidea, Coccoidea or Aleyrodidae.

12. The composition according to claim 6, where the specified bugs pest is at least one pest selected from the group including pests such as aphids, greenhouse Myzus persicae, aphids bocheva Aphis gossypii, bird-cherry aphid is common Rhopalosiphum padi and the Comstock mealybug Pseudococcus comstocki.

13. The compound represented by formula (Ib), or acceptable from the point of view of the agriculture and horticulture Sol specified connection:
[Chemical formula 3]

where Het₁mean 3-pyridyl,
R₁means hydroxyl,
R₂and R₃represent propionyloxy or optionally substituted cyclic With_3-6alkylcarboxylic, and
R₄means hydroxyl,
optionally substituted cyclic With_3-6alkylcarboxylic,
optionally substituted benzoyloxy, or
optionally substituted saturated or unsaturated five - or six-membered heterocyclic, carbonyloxy where the specified heterocyclic selected from the group consisting of pyridyl, teinila, thiazolidinedione and imidazolyl,
provided that the connection
where Het₁mean 3-pyridyl,
R₁means hydroxyl,
R₂and R₃represent propionyloxy and
R₄means hydroxyl,
eliminated.

14. The connection 13 or acceptable from the point of view of the agriculture and horticulture salt of the compounds, where
R₂and R₃represent an optionally substituted cyclic With_3-6alkylcarboxylic and
R₄means hydroxyl, optionally substituted cyclic With_3-6alkylcarboxylic and or optionally substituted benzoyloxy.

15. The connection 13 or acceptable from the point of view of the agriculture and horticulture salt of the compounds, where
R₂and R₃represent propionyloxy,
R₄means optionally substituted cyclic With₃-₆alkylcarboxylic or optionally substituted, pyridylcarbonyl.

16. The composition for use as a means of pest control that contains the connection 13 or acceptable from the point of view of the agriculture and horticulture salt of the compounds as the active ingredient and acceptable from the point of view of the agriculture and horticulture media.

17. Method of combating agricultural pests, comprising applying an effective amount of the compound represented by formula (I)according to claim 1 or acceptable from the point of view of the agriculture and horticulture salts of the compounds on the plant or soil.

18. The way to deal with bugs agricultural pests, comprising applying an effective amount of the compound represented by formula (Ia), according to claim 6 or acceptable from the point of view of the agriculture and horticulture salts of the compounds on the plant or soil.

19. Method of combating agricultural pests, comprising applying effective amounts of the compounds represented by formula (Ib), according to item 13 or acceptable from the point of view of the agriculture and horticulture salts of the compounds on the plant or soil.

20. The use of compounds represented by formula (I)according to claim 1 or acceptable from the point of view of the agriculture and horticulture salts of the compounds as a means of pest control.

21. The use of compounds represented by formula (1A)according to claim 6 or acceptable from the point of view of the agriculture and horticulture salts of the compounds as a means of combating bugs pest control.

22. The use of compounds represented by formula (Ib), according to item 13 or acceptable from the point of view of the agriculture and horticulture salts of the compounds as a means of pest control.