RU2056107C1 - Insecticide-acaricide composition - Google Patents

Abstract

FIELD: organic chemistry. SUBSTANCE: insecticide-acaricide composition has 0.1-40.25 wt.-% compound of the general formula

where R - n. -propyl, tert.-butyl; R′ - H, trifluoromethyl, cyano; AX - hexynyl, butynyloxylmethyl, 3,3-dimethylbutyl, 4-ethynyl, 4-ethynylcyclohexyl; Y′ and Y - are similar and mean oxygen or sulfur; Z - Z-CH₂O,, CH₂S, and the special additives - the rest. Composition is used in agriculture. EFFECT: increased effectiveness of composition. 4 cl, 5 tbl

Description

 The invention relates to a pesticidal composition based on new chemical compounds having pesticidal activity, and is used in pest control. More specifically, the invention relates to a pesticidal composition based on heterobicycloalkanes.

 The use of certain 2,6,7-trioxabicyclo [2.2.2] octanes [1-4] is known. Derivatives of these compounds have been found to exhibit significant pesticidal activity.

(1) где R обозначает С₂-С₁₀-неароматическую гидрокарбильную группу, не обязательно замещенную, или метилзамещенную циано-, гало-, С₁-С₄-алкокси, не обязательно замещенным гало-, или группой S(O)_mR³, где R³ обозначает С₁-С₄-алкил, не обязательно замещенный гало, и m равно 0, 1 или 2, или R обозначает фенил, не обязательно замещенный С₁-С_4-алкокси, С₁-С₃-алкилом, С₂-С₄-алкинилом, гало-, С₁-С₄-галоалкилом, циано- или группой S(O) R³, определенной выше,
R¹ и R² могут быть одинаковыми или различными и каждый обозначает водород, гало- или С₁-С₃-алифатическую группу, не обязательно замещенную гало-, циано-, С₁-С₅-карбалкокси, С₁-С₄-алкокси, или группой S(O)_m'R⁴, где m' обозначает 0, 1 или 2 и R⁴ обозначает С₁-С₄-алкил, циано-, гемдиметил или С₁-С₅-карбалкокси, или R¹ и R² и атомы углерода, к которым они присоединяются, образуют С₅-С₇-карбоциклическое кольцо, не обязательно замещенное гало-, или С₁-С₃-алифатическую или алкоксигруппу,
А-Х содержит 3-20 атомов углерода, где А обозначает С₂-С₁₂-неароматическую гидрокарбильную группу, которая не обязательно содержит 1-6 гетероатомов, которые являются одинаковыми или различными и каждый из которых выбирают из кислорода, серы, азота, фтора или хлора, и каждый из которых не обязательно замещен одной или двумя гидроксильными группами, или A означает CH₂O или группу СН₂S(O)_n, где n равно 0, 1 или 2;
Х обозначает водород, гало-, группу SiR⁵, R⁶, R⁷ или SnR⁵, R⁶, R⁷, где R⁵, R⁶ и R⁷ одинаковые или различные и каждый обозначает гидрокарбильную группу, содержащую до 8 атомов углерода, не обязательно замещенную 1-3 гало, С₁-С₆-алкокси-, С₁-С₆-алкилтило, С₁-С₆-алкилсульфинилом, С₁-С₆-алкилсульфонилом, циано, С₁-С₆-ацилокси или С₁-С₆-карбалкоксигруппами, или, когда один или более R⁵-R⁷обозначают алкинил, тогда он или они не обязательно замещены силилом, замещенным тремя С₁-С₄-алкильными группами, или Х обозначает группу

- R¹⁰ где R⁸ и R⁹ одинаковые или различные и каждый независимо выбирают из водорода, гало, циано, С₁-С₅-карбалкокси, С₁-С₄-алкила, не обязательно замещенного от одного до трех галоатомами, циано, С₁-С₄-карбалкокси, С₁-С₄-алкокси или группой S(O)_m'' R¹¹, где m" равно 0, 1 или 2 и R¹¹обозначает С₁-С₄-алкил, С₁-С₄-алкокси или S(O)_m''' R¹², где m''' равно 0, 1 или 2 и R¹² обозначает С₁-С₄-алкил, не обязательно замещенный 1-3 атомами фтора, или R⁸ и R⁹ и атом углерода, к которому они присоединяются, образуют С₃-С₆-циклоалкильное кольцо, и R¹⁰ обозначает водород, гало-, гидрокси-, циано-, С₁-С₄-алкокси, С₁-С₄-ацилокси, С₁-С₅-карбалкокси или С₁-С₉-гидрокарбильную группу, не обязательно замещенную гидрокси, циано-, С₁-С₄-алкокси, С₁-С₄-ацилокси, С₁-С₄-карбалкокси, 1-3 галоатомами или группой S(O)_m'''' R¹³, где m'''' равно 0, 1 или 1 и R¹³ обозначает С₁-С₄-алкил, или R¹⁰ обозначает группу S(O)_m''''' R¹⁴, где m''''' равно 0, 1 или 2 и R¹⁴ обозначает С₁-С₄-алкил, не обязательно замещенный 1-3 атомами фтора.Thus, the invention provides a compound of the formula:

(1) where R is a C ₂ -C ₁₀ non-aromatic hydrocarbyl group, optionally substituted, or methyl substituted cyano, halo, C ₁ -C ₄ alkoxy, optionally substituted with halo, or a group S (O) _m R ³ , where R ³ is C ₁ -C ₄ alkyl optionally substituted with halo and m is 0, 1 or 2, or R is phenyl optionally substituted with C ₁ -C ₄ alkoxy, C ₁ -C ₃ - alkyl, C ₂ -C ₄ alkynyl, halo, C ₁ -C ₄ haloalkyl, cyano or the group S (O) R ³ as defined above,
R ¹ and R ² may be the same or different and each represents hydrogen, a halo or C ₁ -C ₃ aliphatic group, optionally substituted with a halo, cyano, C ₁ -C ₅ carbalkoxy, C ₁ -C ₄ - alkoxy, or a group S (O) _m 'R ⁴ , where m' is 0, 1 or 2 and R ⁴ is C ₁ -C ₄ alkyl, cyano, heme dimethyl or C ₁ -C ₅ carbalkoxy, or R ¹ and R ² and the carbon atoms to which they are attached form a C ₅ -C ₇ carbocyclic ring, optionally substituted with a halo, or a C ₁ -C ₃ aliphatic or alkoxy group,
AX contains 3-20 carbon atoms, where A represents a C ₂ -C ₁₂ non-aromatic hydrocarbyl group that does not necessarily contain 1-6 heteroatoms that are the same or different and each of which is selected from oxygen, sulfur, nitrogen, fluorine or chlorine, and each of which is optionally substituted with one or two hydroxyl groups, or A means CH ₂ O or a group CH ₂ S (O) _n , where n is 0, 1 or 2;
X is hydrogen, halo, SiR ⁵ , R ⁶ , R ⁷ or SnR ⁵ , R ⁶ , R ⁷ , where R ⁵ , R ⁶ and R ^{7 are the} same or different and each is a hydrocarbyl group containing up to 8 carbon atoms, optionally substituted 1-3 halo, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthylo, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, cyano, C ₁ -C ₆ acyloxy or C ₁ -C ₆ carbalkoxy groups, or when one or more R ⁵ -R ⁷ is alkynyl, then he or they are optionally substituted with silyl substituted with three C ₁ -C ₄ alkyl groups, or X is a group

- R ¹⁰ where R ⁸ and R ^{9 are the} same or different and each is independently selected from hydrogen, halo, cyano, C ₁ -C ₅ carbalkoxy, C ₁ -C ₄ alkyl, optionally substituted with one to three halo atoms, cyano, C ₁ -C ₄ carbalkoxy, C ₁ -C ₄ alkoxy or the group S (O) _m ″ R ¹¹ , where m ″ is 0, 1 or 2 and R ¹¹ is C ₁ -C ₄ alkyl, C ₁ —C ₄ alkoxy or S (O) _m ″ ″ R ¹² , where m ″ ″ is 0, 1 or 2, and R ¹² is C ₁ -C ₄ alkyl optionally substituted with 1 to 3 fluorine atoms, or r ⁸ and r ⁹ and the carbon atom to which they are attached, form a C ₃ -C ₆ cycloalkyl ring, and r ¹⁰ is hydrogen, halo, g droksi-, cyano, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -atsiloksi, C ₁ -C ₅ -karbalkoksi or C ₁ -C ₉ -gidrokarbilnuyu group is not necessarily substituted with hydroxy, cyano, C ₁ - C ₄ -alkoxy, C ₁ -C ₄ acyloxy, C ₁ -C ₄ -carbalkoxy, 1-3 halo atoms or the group S (O) _m ″ ″ R ¹³ , where m ″ ″ is 0, 1 or 1 and R ¹³ is C ₁ -C ₄ alkyl, or R ¹⁰ is a group S (O) _m ″ ″ ″ R ¹⁴ where m ″ ″ ″ is 0, 1 or 2 and R ¹⁴ is C ₁ -C ₄ -alkyl, optionally substituted with 1-3 fluorine atoms.

Y and Y ^{1 are the} same or different and each is selected from oxygen and S (O) _n ', where n' is 0, 1 or 2. Z is CH ₂ CH ₂ , CH ₂ O or CH ₂ S (O) _n ", where n "is 0, 1 or 2.

- R¹⁰, где R⁸, R⁹ и R¹⁰ имеют вышеприведенные значения, за исключением того, что R⁸ и R⁹ не обозначают водород.Provided that when A does not contain a fragment C = C, X denotes a group

- R ¹⁰ where R ⁸ , R ⁹ and R ¹⁰ have the above meanings, except that R ⁸ and R ^{9 are} not hydrogen.

 In the determination of Z, the first atom mentioned is adjacent to position 4 of the bicyclic ring system.

 When R is an alkyl, alkenyl or alkynyl, cycloalkyl or cycloalkenyl group, which preferably contains up to 6 carbon atoms. It is convenient when R is substituted so that there are up to 7 substituents when the substituent is fluoro, 3 substituents when the substituents are chloro or bromo, or 1 substituent when it is other than halo.

Suitably, if R is an aliphatic or alicyclic group containing from 2 to 8 carbon atoms, or phenyl, each of them is optionally substituted with cyano, 1-7 halo atoms, C ₁ -C ₄ alkoxy or the group S (O) _m R ⁴ defined above. Most suitable when R is propyl, butyl, pentyl, C ₂ -C ₅ alkenyl or alkynyl, cyclopropylmethyl, C ₃ -C ₇ cycloalkyl or phenyl, each of which is optionally substituted with fluoro, chloro or bromo, for example, n- propyl, n-butyl, i-butyl, sec-butyl, t-butyl, prop-2-enyl, 2-methylprop-2-enyl, but-3-enyl, phenyl, cyclopentyl or cyclohexyl. Preferably, when R is n-propyl, n-butyl, i-butyl, t-butyl or phenyl.

Suitably, if R ¹ is hydrogen, halo, cyano, methyl or ethyl, each of which is optionally substituted with cyano, methoxy, methylthio, chloro, bromo or fluoro. Most suitable if R ¹ is hydrogen, methyl, cyano, trifluoromethyl or ethyl. Preferably, when R ¹ is hydrogen, methyl, cyano or trifluoromethyl.

Suitable if R ² is hydrogen, cyano, methyl or trifluoromethyl. Most suitable if R ² is hydrogen or methyl. Preferably, if R ² is hydrogen.

Preferably, when Z is CH ₂ S or CH ₂ O.

Suitable if Y and Y ¹ are selected from oxygen or sulfur.

, группу -СН=СН(СН₂)₂С≡С-, группу СН₂О(СН₂)₂С≡С-, группу -(СН₂)₃СН-(СН₃)-С≡С-, группу -(СН₂)₂СН(СН₃)СН₂С≡С-, группу-СН₂СН-(СН₃) (СН₂)₂- С≡С-, группу (СН₂)₂СН=СН С≡ С- или группу -(СН₂)₃С≡С- и Х обозначает С₁-С₄-алкил, не обязательно замещенный гидрокси-, С₁-С₄-алкокси или С₁-С₄-ацилокси или 1-3 галоатомами. Во втором предпочтительном варианте А обозначает -СН₂СН₂-, -СН=СН- или С≡С-группу и Х обозначает группу

- R¹⁰. Пригодно, когда R⁸, R⁹ и R¹⁰ каждый выбирают из хлоро, бромо, метокси или метила, не обязательно замещенного метокси или фторо.Suitable if A is a C ₂ -C ₈ non-aromatic hydrocarbyl group that does not necessarily contain 1-3 heteroatoms, as defined above. In one preferred embodiment, A is a C ₅ -C ₈ non-aromatic hydrocarbyl group that optionally contains one heteroatom and ends in a -C≡C moiety adjacent to X. Preferably A is a - (CH ₂ ) ₄ C≡C- group

the group —CH = CH (CH ₂ ) ₂ C≡C—, the group CH ₂ O (CH ₂ ) ₂ C≡C-, the group - (CH ₂ ) ₃ CH- (CH ₃ ) —C≡C-, the group - (CH ₂ ) ₂ CH (CH ₃ ) CH ₂ С≡С-, group-СН ₂ СН- (СН ₃ ) (СН ₂ ) ₂ - С≡С-, group (СН ₂ ) ₂ СН = СН С≡ C- or group - (CH ₂ ) ₃ C≡C- and X is C ₁ -C ₄ alkyl optionally substituted with hydroxy, C ₁ -C ₄ alkoxy or C ₁ -C ₄ acyloxy or 1-3 haloatoms. In a second preferred embodiment, A is —CH ₂ CH ₂ -, —CH═CH— or a C≡C group, and X is a group

- R ¹⁰ . Suitable when R ⁸ , R ⁹ and R ^{10 are} each selected from chloro, bromo, methoxy or methyl, optionally substituted with methoxy or fluoro.

The compounds of formula (1) can exist in a variety of isomeric forms. The present invention provides single isomers of compounds of formula (1) and mixtures thereof. The present invention also encompasses compounds of formula (1) containing radioactive isotopes, in particular those in which one carbon atom is C ¹⁴ or 1-3 hydrogen atoms substituted with tritium.

(C ≡ C)_q R¹⁵(C ≡ C)_t X⁹
(2) где R^a обозначает С₂-С₁₀-алкил, алкенил или алкинил, каждый не обязательно замещен, или метилзамещен, циано-, гало-, С₃-С₄-циклоалкилом, не обязательно замещенным гало, С₁-С₄-алкокси, не обязательно замещенным гало, или группой S(O)_mR³, определенной выше, или R^a обозначает С₃-С₁₀-циклоалкил, С₄-С₁₀-циклоалкенил или фенил, каждый не обязательно замещен С₁-С₄-алкокси, С₁-С₃-алкилом, не обязательно замещенным до трех галоатомами, С₂-С₄-алкинилом, гало-, циано- или группой S(O)_mR³, определенной выше;
R^1a и R^2a могут быть одинаковыми или различными и каждый обозначает водород, гало или алифатическую группу, содержащую до 3 атомов углерода, не обязательно замещенную гало, циано, С₁-С₄-алкокси или группой S(O)_mR⁴, определенной выше; алкилкарбалокси, содержащую до 6 атомов углерода, или алкинил, замещенный три-С₁-С₄-алкилсилилом, или R^1aобозначает СОО-С₁-С₄-алкил, циано, гемдиметил, или R^1a и R^a и атомы углерода, к которым они присоединены, образуют С₅-С₇-карбоциклическое кольцо, не обязательно замещенное гало-, С₁-С₃-алкилом или алкокси или С₂-С₃-алкенилом;
R¹⁵ обозначает простую связь или группу R^15', где R^15' обозначает группу

a или не обязательно замещенную 1-5 метиловыми группами или галоатомами, где W обозначает кислород, группу S(O)_р, где р равно 0, 1 или 2, или (CH₂)_r, где r равно1, 2 или 3, и фрагмент (С≡ С)_tХ^а присоединяется к положению а или b кольца, или R^15' обозначает алифатическую цепь, содержащую 1-8 атомов углерода, где один или два гетероатома могут быть помещены, причем цепь или R^15' не обязательно замещена 1-4 заместителями, которые могут быть одинаковыми или различными и которые независимо друг от друга выбирают из гидрокси-, оксо-, гало-, С₁-С₄-алкила или С₁-С₄-алкокси, каждый из которых не обязательно замещен не более чем тремя галоатомами, С₁-С₄-ацилокси, эпокси-, С₁-С₄-алкилиденовой группой, С₁-С₆-карбалкокси-группой, циано, группой S(O)_p'R^4a, где p' равно 0, 1 или 2 и R^4a обозначает С₁-С₄-алкил, Х^а выбирают из водорода, гало-, С₁-С₁₀-гидрокарбила, не обязательно замещенного гидрокси-, С₁-С₄-алкокси- или С₁-С₄-ацилоксигруппой или 1-3 галоатомами, или Х^аобозначает группу SiR^5aR^6aR^7a или SnR^5aR^6aR^7a, где R^5aR^6a и R^7a-одинаковые или различные и каждый обозначает гидрокарбильную группу, содержащую до 6 атомов углерода, не обязательно замещенную 1-3 гало-, циано-, алкокси-, алкилтио-, ацилокси- или карбалкоксигруппами, содержащими до 6 атомов углерода, или Х^а обозначает группу R¹⁶ ОСО, где R¹⁶ обозначает С₁-С₄-алкил. q обозначает 0 или 1 и t обозначает 1 или 2 при условии, что сумма q и t не превышает 2,
Y и Y¹ одинаковые или различные и каждый выбирают из кислорода и S(O)_n', где n' равно 0, 1 или 2; Z обозначает СН₂О или СН₂S(O)_n'', где n" равно 0, 1 или 2, за исключением того, что Х^а не может быть водородом, когда q равно 0, t равно 1 и R¹⁵ обозначает простую связь.One preferred group of compounds of the present invention are compounds of the formula:
R

(C ≡ C) _q R ¹⁵ (C ≡ C) _t X ⁹
(2) where R ^a is C ₂ -C ₁₀ alkyl, alkenyl or alkynyl, each is optionally substituted, or methyl substituted, cyano, halo, C ₃ -C ₄ cycloalkyl optionally substituted with halo, C ₁ -C _4- alkoxy, optionally substituted with halo, or with the group S (O) _m R ³ as defined above, or R ^a is C ₃ -C ₁₀ cycloalkyl, C ₄ -C ₁₀ cycloalkenyl or phenyl, each optionally substituted with C ₁ -C ₄ alkoxy, C ₁ -C ₃ alkyl optionally substituted with up to three halo atoms, C ₂ -C ₄ alkynyl, halo, cyano or S (O) _m R ³ group as defined above;
R ^1a and R ^2a may be the same or different and each represents a hydrogen, halo or aliphatic group containing up to 3 carbon atoms, optionally substituted by halo, cyano, C ₁ -C ₄ alkoxy or the group S (O) _m R ⁴ , defined above; alkylcarbalkoxy containing up to 6 carbon atoms, or alkynyl substituted with tri-C ₁ -C ₄ -alkylsilyl, or R ^1a is COO-C ₁ -C ₄ -alkyl, cyano, heme dimethyl, or R ^1a and R ^a and carbon atoms, to which they are attached, form a C ₅ -C ₇ carbocyclic ring, optionally substituted with halo, C ₁ -C ₃ alkyl or alkoxy or C ₂ -C ₃ alkenyl;
R ¹⁵ denotes a single bond or a group R ^{15 '} , where R ^15' denotes a group

a or optionally substituted with 1-5 methyl groups or halo atoms, where W is oxygen, a group S (O) _p , where p is 0, 1 or 2, or (CH ₂ ) _r , where r is 1, 2 or 3, and fragment (S≡ C) _t X ^a is attached to the a or b position of the ring, or R ^{15 'is} an aliphatic chain containing 1-8 carbon atoms wherein one or two heteroatoms may be placed, wherein the chain or R ^15' is not necessarily substituted 1-4 substituents, which may be the same or different and which are independently selected from hydroxy, oxo, halo, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alk hydroxy, each of which is not necessarily substituted by no more than three halo atoms, a C ₁ -C ₄ acyloxy, epoxy, C ₁ -C ₄ alkylidene group, a C ₁ -C ₆ carbalkoxy group, cyano, a group S (O ) _p 'R ^4a , where p' is 0, 1 or 2 and R ^4a is C ₁ -C ₄ -alkyl, X ^{a is} selected from hydrogen, halo, C ₁ -C ₁₀ -hydrocarbyl, optionally substituted with hydroxy, A C ₁ -C ₄ alkoxy or C ₁ -C ₄ acyloxy group or 1 to 3 halo atoms, or X ^a is a SiR ^5a R ^6a R ^7a or SnR ^5a R ^6a R ^7a group, where R ^5a R ^6a and R ^7a are identical or different and each denotes a hydrocarbyl group containing up to 6 carbon atoms an ode optionally substituted with 1 to 3 halo, cyano, alkoxy, alkylthio, acyloxy or carbalkoxy groups containing up to 6 carbon atoms, or X ^a is an R ¹⁶ OCO group, where R ¹⁶ is C ₁ -C ₄ - alkyl. q is 0 or 1 and t is 1 or 2, provided that the sum of q and t does not exceed 2,
Y and Y ^{1 are the} same or different and each is selected from oxygen and S (O) _n ′, where n ′ is 0, 1 or 2; Z is CH ₂ O or CH ₂ S (O) _n ″, where n ″ is 0, 1 or 2, except that X ^a cannot be hydrogen when q is 0, t is 1 and R ¹⁵ is simple connection.

 Suitable heteroatoms for placement in an alkylene chain include oxygen, nitrogen, and sulfur, with sulfur not necessarily oxidized as sulfoxide or sulfone. The oxygen and nitrogen atoms can adjoin each other, in which case they can form an oxime.

Suitable and preferred values for the groups R ^a , R ^1a , R ^2a , Y, Z, and Y ^{1 are} defined above for the groups R, R ¹ , R ² , Y, Z, and Y ^1, respectively. Suitable if R ¹⁵ denotes a single bond, a 1,4-cyclohexyl group or an aliphatic chain, as defined above, which has 2-6 carbon atoms, not necessarily placed by an oxygen or sulfur atom. Suitable when X ^a is hydrogen, C ₁ -C ₃ alkoxymethyl or a SiR ¹⁷ R ¹⁸ R ¹⁹ group, where R ¹⁷ , R ¹⁸ and R ^{19 are the} same or different and each is C ₁ -C ₄ alkyl. Preferably, if n is 0.

(3) где R^a, R^1a, R^2a, X^a, Y, Y¹, Z и t имеют вышеприведенные значения и R^15aобозначает простую связь или группу R^15', определенную выше.One preferred group of compounds of formula (1) of the present invention are compounds of formula

(3) where R ^a , R ^1a , R ^2a , X ^a , Y, Y ¹ , Z and t have the above meanings and R ^15a is a single bond or a group R ^{15 ′} as defined above.

Suitable if R ^1a is 1,4-cyclohexyl, t is 1 and X ^a is hydrogen or C ₁ -C ₄ alkyl optionally substituted with hydroxy, C ₁ -C ₄ alkoxy or C ₁ -C ₄ - an acyloxy group, or 1-3 halo atoms, or R ^15a denotes a single bond, t is 1 and X ^a is C ₁ -C ₄ alkyl optionally substituted with hydroxy, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxy group or 1-3 halo atoms. X ^{a is} preferably a tertiary group. Preferably, if R ^15a is cyclohexyl and X ^a is hydrogen, or R ^15a is a single bond and X ^a is tertiary butyl.

B-D-

R²⁰,
(4) где R^b обозначает С₂-С₁₀-неароматическую гидрокарбильную группу, не обязательно замещенную циано-, гало-, С₁-С₄-алкокси или группой S(O)_mbR^3b, где R^3b обозначает С₁-С₄-алкил и m^b равно 0, 1 или 2, или R^bобозначает фенил, не обязательно замещенный С₁-С₄-алкокси, С₁-С₃-алкилом, С₂-С₄-алкинилом, гало-, С₁-С₄-галоалкилом, циано- или группой S(O)_nbR^3b, определенной выше.Another preferred group of compounds of the present invention includes compounds of the formula:
R

Bd-

R ²⁰ ,
(4) where R ^b is a C ₂ -C ₁₀ non-aromatic hydrocarbyl group, optionally substituted with cyano, halo, C ₁ -C ₄ alkoxy or S (O) _m bR ^3b , where R ^3b is C ₁ - C ₄ -alkyl and m ^b is 0, 1 or 2, or R ^b is phenyl, optionally substituted with C ₁ -C ₄ alkoxy, C ₁ -C ₃ -alkyl, C ₂ -C ₄ -alkynyl, halo, With ₁ -C ₄ haloalkyl, cyano or S (O) _n bR ^3b group as defined above.

R ^1b and R ^2b may be the same or different and each represents hydrogen, a halo or C ₁ -C ₃ aliphatic group, optionally substituted with a halo, cyano, C ₁ -C ₅ carbalkoxy or C ₁ -C ₄ - alkoxy; a group S (O) _m 'R ⁴ , where m' is 0, 1 or 2 and R ⁴ is C ₁ -C ₄ alkyl; C ₂ -C ₃ alkynyl, cyano, heme dimethyl or C ₁ -C ₅ carbalkoxy, or R ^1b and R ^b and the carbon atoms to which they are attached form a C ₅ -C ₇ carbocyclic ring, optionally substituted halo, C ₁ -C ₃ -alkyl or alkoxy or C ₂ -C ₃ -alkenyl.

R ⁸ , R ⁹ are as defined above, R ²⁰ is an R ⁸ group as defined above.

B denotes a single bond, a methylene or C ₂ -C ₆ aliphatic chain, which may contain one or two heteroatoms and / or double bonds, but not triple bonds introduced into the chain, and which may be substituted by 1-4 substituents, the same or various, each of which is independently selected from hydroxy, oxo, halo, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ acyloxy, epoxy, C ₁ -C ₄ an alkylidene group, a C ₁ -C ₆ carbalko group, a C ₁ -C ₄ haloalkyl or cyano.

D is a single bond or a group CH ₂ O, CH ₂ S (O) _n , where n is 0, 1 or 2, or D is a 1,2-cyclopropyl group.

Y and Y ¹ as well as Z have the above meanings, provided that B cannot be a single bond or a methylene group when D is a single bond.

Suitable when R ^b is propyl, butyl, pentyl, C ₂ -C ₅ alkenyl or alkynyl, C ₅ -C ₇ cycloalkyl or phenyl, each of which is optionally substituted with fluoro, chloro or bromo. Most suitable if R ^b is n-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, phenyl, cyclopentyl or cyclohexyl, and preferably if R ^b is n-propyl, n-butyl, and butyl or tert-butyl.

Suitable when R ^1b is hydrogen, cyano, methyl or ethyl, each of which is optionally substituted with cyano, methoxy, methylthio, chloro, bromo or fluoro. Most suitable if R ^1b is hydrogen, methyl, cyano, trifluoromethyl or ethyl. Preferably, if R ^1b is hydrogen, methyl, cyano or trifluoromethyl.

 Suitable heteroatoms for inclusion in B are oxygen, nitrogen and sulfur, and sulfur is not necessarily oxidized as sulfoxide or sulfone.

Suitable if R ⁸ , R ²⁰ and R ^{9 are} each selected from chloro, bromo, methoxy or methyl, optionally substituted with methoxy or fluoro.

Suitable if B is a group (CH ₂ ) ₂ or —CH═CH—.

 Suitable if D is a single bond.

Suitable and preferred values for the groups R ^2b , Z, Y, and Y ′ are defined above for the groups R ² , Z, Y, and Y ′, respectively.

Preferred compounds of the present invention include:
1- (Hex-5-ynyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane
1- (Pent-4-ynyl) -4-propyl-3-trifluoromethyl-2,6,7-trioxabicyclo [2.2.2] octane
1- (Hex-5-ynyl) -4-propyl-3-trifluoromethyl-2,6,7-trioxabicyclo [2.2.2] octane
1- (Pent-4-ynyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (Hex-5-ynyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
4- (Cyclohexyl) -1- (pent-4-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane
4- (Cyclohexyl) -1- (hex-5-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane
4-tert-Butyl-1- (hex-5-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane
4-tert-Butyl-1- (6-trimethylsilylhex-5-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane
1- (4-Ethinylcyclohexyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane
4-tert-Butyl-1- (4-ethynylcyclohexyl) -2, 6,7-trioxabicyclo [2.2.2] octane (cis and trans isomers)
4-tert-Butyl-1- (3,3-dimethylbut-1-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane 1- (3,3-dimethylbut-1-ynyl) -4-propyl -2,6,7-trioxabicyclo [2.2.2] octane-3-carbon it-ril
4-tert-Butyl-1- (hex-5-ynyl) -2,6,7-dioxa-7-thiabicyclo [2.2.2] octane
1- (Hex-5-ynyl) -4-propyl-2-oxa-6,7-diabiabicyclo [2.2.2] octane
1- (Hex-5-ynyl) -4-propyl-2,6,7-trithiabicyclo [2.2.2] octane
4-tert-Butyl-1- [2- (prop-2-ynylthio) ethyl] -2,6,7-trioxabicyclo [2.2.2] octane 4-Propyl-1- [2- (prop-2-ynylthio) ethyl] -2,6,7-trioxabicyclo [2.2.2] octane 4-tert-butyl-1- [2- (prop-2-ynoxyloxy) ethyl] -2,6,7-trioxabicyclo [2.2.2 ] octane
4-Propyl-1- [2- (prop-2-ynyloxy) ethyl] -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (But-3-yniloxymethyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane
4-tert-Butyl-1-but-3-yniloxymethyl) -2, 6,7-trioxabicyclo [2.2.2] octane 1- (but-3-yniloxymethyl) -4-propyl-2,6,7-trioxabicyclo [ 2.2.2] octane-3-carbonite -ri
4-tert-Butyl-1- (hept-6-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane
1- (Hept-6-ynyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane
4-Butyl-1- (hex-5-ynyl) -2,6,7-trioxab-acyclo [2.2.2] octane-3-carbonitrile
1- (Hex-5-ynyl) -4- (2-methylprop-2-enyl) -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (Hex-5-ynyl) -4- (prop-2-enyl) -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (Hex-5-ynyl) -4- (prop-2-enyl) -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (But-3-yniloxymethyl) -4- (prop-2-enyl) -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
4- (But-3-enyl) -1- (hex-5-ynyl) -2,6,7-tri-oxabicyclo [2.2.2] octane-3-carbonitrile
4-tert-Butyl-1- (4-methylhex-5-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane
1- [2-But-3-ynyloxy) ethyl] -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane
1- [1- (But-3-ynyloxy) ethyl] -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane
1- (But-3-ynylthiomethyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane
4-tert-Butyl-1- (but-3-ynylthiomethyl) 2,6,7-trioxabicyclo [2.2.2] octane
4-Butyl-1- (hex-5-ynyl) -2-oxa-6,7-dithi-abicyclo [2.2.2] octane
4-tert-Butyl-1- (hex-5-ynyl) -2-oxa-6,7-diabiabicyclo [2.2.2] octane
4-tert-Butyl-1- (hex-5-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (Hex-5-ynyl) -4-isobutyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
4-Ethoxymethyl-1- (hex-5-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (1-methylhex-5-ynyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane
4-tert-Butyl-1- (1-methylhex-5-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane
1- (1-Methylhex-5-ynyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
Methyl-7- (4-propyl-2,6,7-trioxabicyclo [2.2.2] oct-1-yl) hepta-2-inoate
1- (Hex-5-ynyl) -4-phenyl-2,6,7-trioxa-bicyclo [2.2.2] octane
1- (Hex-5-ynyl) -4-isobutyl-2-oxa-6,7-dithiabicyclo [2.2.2] octane 1- (Hex-5-ynyl) -3-methyl-4-propyl-2-ok -sa-6,7-dithiabicyclo [2.2.2] octane
1- (3-Methylhex-5-ynyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (2-Methylhex-5-ynyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (3,3-Dimethylbuti-1-ynyl) -4-isobutyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (But-3-yniloxymethyl) -4-propyl-2,6,7-trithiabicyclo [2.2.2] octane
1- (trans-4) e (-ethynylcyclohexyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
4-Propyl-1 - [(E / Z) -6- (trimethylsilyl) hex-3-en-5-ynyl] -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- [E / Z) -Hex-3-en-5-ynyl] -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile (E: Z 1: 2)
1 - [(E / Z) -7-Methoxyhept-3-en-5-ynyl] -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile (E: Z 1: 2 )
1 - [(E / Z) -7-Hydroxyhept-3-en-5-ynyl] -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
4-tert-Butyl-1 - [(E) -hex-1-en-5-ynyl] -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
4-Propyl-2,6,7-trioxabicyclo [2.2.2] octane-1-carboxaldehyde oxime O- (prop-2-ynyl) ether
1- (Hex-5-ynyl) -4-isobutyl-2,6,7-trity-abicyclo [2.2.2] octane
1- (Hex-5-ynyl) -4-phenyl-2-oxa-6,7-di-thiabicyclo [2.2.2] octane
4-Propyl-1- (4-methylhex-5-ynyl) -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
4-Ethyl-1- (hex-5-ynyl) -2,6,7-tritiabi-cyclo [2.2.2] octane
1- (Hex-5-ynyl) -4-phenyl-2,6,7-trioxa-bicyclo [2.2.2] octane-3-carbonitrile
4-Cyclopropylmethyl-1- (hex-5-ynyl) -2, 6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile 4-Isobutyl-1- (3-methylhex-5-ynyl) 2.6, 7-trioxabicyclo [2.2.2] octane-3-carbonitrile 1 - [(S) -3-Methylhex-5-ynyl] -4-propyl-2,6,7-trioxabicyclo [2.2.2] octan-3- carbo nitrile
1- (2-Methylhex-5-ynyl-4-propyl-2-enyl) -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
4-tert-Butyl-1- (3,3-dimethylbutyl) 2,6,7-trioxabicyclo [2.2.2] octane
1- (3,3-Dimethylbutyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1 - [(E) -3,3-Dimethylbut-1-enyl] -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile 1- (tert-butylthiomethyl) -4-propyl -2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitre il
1 - [(Z) -1-fluoro-3,3-dimethylbutyl-1-enyl] -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane-3-carbonitrile
1- (Hept-5-ynyl) -4-propyl-2,6,7-trioxabicyclo [2.2.2] octane
By the term “hydrocarbyl” group is meant alkyl, alkenyl (including cyclic alkyl and alkenyl, as well as alkyl and alkenyl substituted with cyclic alkyl and alkenyl), alkynyl, aryl and aralkyl groups. “Hydrocarbyloxy” means a hydrocarbyl group as defined above when attached to oxygen. By the term “aliphatic” group is meant an alkyl, alkenyl or alkynyl group. By the term “halo” is meant fluoro, chloro, bromo or iodine.

(5) где R, R¹, R², А и Х имеют вышеприведенные значения, в присутствии кислотного катализатора. Этерат трехфтористого бора является особенно предпочтительным кислотным катализатором для этой циклизации, которую обычно осуществляют в инертном растворителе, таком как галоидзамещенный углеводород, как правило, дихлорметан при температуре окружающей среды или ниже таковой, например от -100 до 50^оС и, как правило, от -70 до -25^оС.The compounds used in the present invention can be obtained by any method known in the art for the preparation of similar compounds, for example, when Y and Y ¹ are hydrogen and Z is CH ₂ O, by cyclization of a compound of the formula:

(5) where R, R ¹ , R ² , A and X are as defined above, in the presence of an acid catalyst. Boron trifluoride etherate is a particularly preferred acid catalyst for this cyclisation which is usually performed in an inert solvent such as a halogenated hydrocarbon, typically dichloromethane at ambient temperature or below per se, for example from -100 ^to 50 ° C and usually from -70 to -25 ^about C.

 The compounds of formula (1) are part of the pesticidal composition and can be used to control pests such as arthropods, for example insects and acarid pests, and parasitic worms. Thus, the invention provides a method for controlling arthropods and / or helminths (parasitic worms), which comprises applying an arthropod-effective amount of a compound of the formula (1) to an arthropod and / or helminth, or to their environment. The invention also provides a method for controlling and / or killing infections by arthropods and / or helminths of animals (including humans) and / or plants (including trees) and / or stored products, which comprises applying to an animal or locus an effective amount of a compound of formula (1) . The present invention also provides compounds of formula (1) for use in human and veterinary medicine, in a public health department, and in agriculture for controlling arthropods and / or helminth pests.

 The compounds of formula (1) are of particular value in the protection of field, fodder, perennial (on the plantation), greenhouse, garden and vineyard crops, ornamental plants, as well as plantation and forest trees, for example, cereals (corn, wheat, rice, sorghum) , cotton, tobacco, vegetables and salads (legumes, cabbage, lettuce, onions, tomatoes and peppers), field crops (potatoes, sugar beets, peanuts, cultivated soybeans, turnips), sugarcane, fodder (corn, sorghum, alfalfa) plantations (tea, coffee, cocoa, banana, oilseed lemon, coconut, rubber, spices), garden and forest (stone fruits and single-seed fruits, citrus fruits, avocados, mangoes, olives and nuts), vineyards, ornamental plants, flowers and shrubs under glass and in gardens and parks, trees (as falling and evergreen) in forests, nurseries, and plantations.

 They are valuable in protecting drill timber (standing, felled, processed, or building) from attack by sawflies (e.g. Urocerus) or beetles (scolithids, platipodids, lactides, bostrichids, kerambicides, anobiids).

 The compounds of formula (1) are used to protect stored products, such as grains, fruits, nuts, spices, tobacco, either in whole form, crushed, or in molded products, from moths, beetles and ticks. They also protect stored animal products, such as leather, hair, wool and feathers in natural or processed form (for example, in the form of carpets or textiles) from the attack of moths and beetles, and also protect meat and fish from the attacks of beetles, ticks and flies .

 The compounds of general formula (1) are valuable in the control of arthropods or helminths, which are harmful or act as carriers of diseases for humans and domestic animals, for example those mentioned above, and especially in the fight against ticks, lice, fleas, small dipterans insects and biting and annoying flies.

 The compounds of formula (1) can be used for such purposes by applying the compounds themselves or in diluted form in a known manner as an impregnating composition, sprayable material, fog, varnish, foam, dust, powder, aqueous suspension, paste, gel, cream, shampoo, grease, flammable solid, evaporative turf, flake, seed, feed additive, wettable powder, granule, aerosol, emulsifiable concentrate, oil suspension, pressure packaging, impregnation product or other their standard formulations well known to those skilled in the art. The impregnation concentrates are not applied perse, but diluted with water, and the animals are immersed in an impregnation bath containing an impregnation wash. Sprayable material can be applied manually or using a spray channel or arch. Treated animals, soil, plants or the surface can be saturated with the sprayed material by introducing small or ultra-small doses. Aqueous suspensions may be applied in the same manner as spray materials or impregnation formulations. Dusts can be scattered using a powder-based spreader, or, in the case of processing animals, introduced into perforated bags attached to trees or rods. Pastes, shampoos and lubricants can be applied manually or scattered on the surface of an inert material, such as that rubbed by animals, and transfer materials to their skin. Poured formulations are scattered as a unit of small volume liquid onto the spokes of the animals so that all or most of the liquid remains on the animals.

 The compounds of formula (1) can be obtained either in the form of compositions ready for use on animals, plants or surfaces, or in the form of compositions that need to be diluted before use, however, both types of composition contain a compound of formula (1) in a mixture with one or more carriers or diluents. The carriers may be liquid, solid or gaseous, or contain mixtures of such substances. The compound of formula (1) may be present at a concentration of from 0.025 to 99% by weight to volume, depending on whether further dilution of the composition is necessary or not.

 Dusts, powders and granules, as well as other solid compositions contain a compound of formula (1) in a mixture with a powdery solid inert carrier. For example, clays, kaolin, bentonite, attapulgite, absorbent carbon black, talc, mica, chalk, gypsum, tricalcium phosphate, powdered cork, magnesium silicate, vegetable carriers, starch and diatomaceous earth are suitable. Such solid compositions are generally prepared by impregnating solid diluents with solutions of the compound of formula (1) in volatile solvents, evaporating the solvents and, if necessary, grinding the products so as to obtain powders and, if desired, granulating, compacting or encapsulating the products.

 The sprayable materials of the compound of formula (1) may contain a solution in an organic solvent or an emulsion in water (dummy washing or irrigated washing) obtained in a field of emulsifiable concentrate (known as water miscible oil), which can also be used for dipping. The concentrate preferably contains a mixture of the active component with or without addition of an organic solvent and one or more emulsifiers. Solvents can be present over a wide range, however, preferably in an amount of 0-90% by weight to volume of the composition, and can be selected from kerosene, ketone, alcohols, xylene, aromatic naphtha and other solvents known in the formulation technology. The concentration of emulsifiers can vary within wide limits, however, preferably in the range of 5 to 25% by weight to volume. Emulsifiers are typically nonionic surfactants, including polyoxyalkylene esters of alkyl phenols and polyoxyethylene derivatives of hexite anhydrides, as well as anionic surfactants, including sodium lauryl sulfate, fatty alcohol ether sulfates, sodium and calcium salts of alkylarylsulfonyl sulfonates. Cationic emulsifiers include benzalkonium chloride and quaternary ammonium ethosulfates.

 Amphoteric emulsifiers include carboxymethylated oleic imidazoline and alkyldimethyl betaine.

 Evaporative turfs usually contain a mixture of cotton and cellulose, compressed into a tile measuring approximately 35 x 22 x 3 mm, treated with 0.3 ml of concentrate containing the active ingredient in an organic solvent and (optionally) an antioxidant, dye and flavor. The insecticide is evaporated using a heat source such as an electrically controlled sod heater.

 Flammable solids usually contain wood powder and a binder mixed with the active ingredient and formed into curly (usually spiral) strips. Dye and fungicide may be added.

 Wettable powders contain an inert solid carrier, one or more surfactants, and, optionally, stabilizers and / or antioxidants.

 Emulsifiable concentrates contain emulsifiers and often an organic solvent such as kerosene, ketones, alcohols, xylenes, aromatic naphthas and other known solvents. Wettable powders and emulsifiable concentrates usually contain from 5 to 95 wt. active component and diluted, for example, with water before use.

 Varnishes contain a solution of the active component in an organic solvent along with a resin and (optionally) a plasticizer.

 Dummy washes can be obtained not only from emulsifiable concentrates, but also from wettable powders, soap-based impregnations and aqueous suspensions containing a compound of formula (1) in a mixture with a dispersing agent and one or more surfactants.

 Aqueous suspensions of the compounds of formula (1) may contain a suspension in water together with suspending, stabilizing or other agents. Suspensions or solutions may be applied perse or in a diluted form.

 Lubricants (or ointments) can be obtained from vegetable oils, synthetic esters of fatty acids or wool fat together with an inert base such as low melting paraffin. The compound of formula (1) is preferably applied through a mixture in solution or suspension. Lubricants can also be made from emulsifiable concentrates by diluting them with an ointment base.

 Pastes and shampoos are semi-solid preparations in which the compound of formula (1) may be present as a uniform dispersion in a suitable base, such as low melting or liquid paraffin, or on a non-greasy basis with glycerin, gum arabic or a suitable soap. Since lubricants, shampoos, and pastes are usually applied without further dilution, they should contain an appropriate percentage of the compound of formula (1) required for processing.

 Spray aerosols can be prepared as a solution of the active component in a spray aerosol and a cosolvent such as halogenated alkanes and solvents mentioned above. Poured formulations can be prepared as a solution or suspension of a compound of formula (1) in a liquid medium. A bird or mammal can also be protected from infection with acaricidal ectoparasite by carrying a suitably molded, curly plastic article soaked in a compound of formula (1). Such products include impregnated collars, labels, dressings, tablets and strips, usually attached to suitable parts of the body. Suitable if the plastic is polyvinyl chloride (PVC).

 The concentration of the compound of formula (1) for application to an animal, internal or external zones will vary according to the selected compound, the interval between treatments, the nature of the composition and infection, however, as a rule, from 0.001 to 20.0% in terms of weight to volume, and preferably from 0.01 to 10% of the compound should be present in the composition. The amount of the compound applied to the animal will vary in accordance with the methods of application, the size of the animal, the concentration of the compound in the applied composition, the factor by which the composition is diluted, and the nature of the composition, as a rule, will be in the range of 0.0001-0.5 wt. with the exception of undiluted formulations, such as poured formulations, which are applied at a concentration in the range of 0.1-20.0%, preferably 0.1-10%, The amount of compound applied to stored products is typically 0.1-20 ppm. Sprayed materials at a distance can be used to obtain an average initial concentration of 0.001-1 mg of the compound of formula (1) per cubic meter of treated space.

 The compounds of formula (1) are used in the protection and treatment of plant species. An effective insecticidal, acaricidal or nematicidal amount of the active component is applied. The dose of application will vary in accordance with the selected compound, the nature of the composition, method of application, plant species, density of planting and infection, as well as other factors. As a rule, a suitable use dose for crops is 0.001-3 kg / ha, preferably 0.01-1 kg / ha. Typical formulations for agricultural use contain 0.0001-50% of the compounds of formula (1) and 0.1-15 wt. compounds of formula (1).

 Dusts, lubricants, pastes and sprays are usually used randomly, as described above, and concentrations of 0.001-20% in terms of weight to volume of the compound of formula (1) in the applied composition can be used).

 The compounds of formula (1) were found to be active against the common housefly (Musca domestica). In addition, certain compounds of formula (1) are active against other arthropod pests, including Myzus persical, Getranychus urtical Plutella xylostella, Culex spp. Gribolium castaneum, Sitophilus granarius, Periplaneta amiercana and Blatella germanica. The compounds of formula (1) are useful in combating arthropods, for example insects and acaricides, in any environment, for example, in agriculture, livestock farming, in domestic situations.

 Insect pests include members of the order (e.g., Anobium Ceutorhynchus, Phynchophorus, Cosmopolites, Zissorhoptrus, Meligethes, Hypothenemus, Hylesinus, Acalymma, Lenea, Phylliodes, Leptinotarsa, Citomitoniforida, Permonium, Cholephidae, Pholepidae, Pholepidae, Pholepidae, Pholepidae -nomus or Anthrenus spp.), Lepidoptera (e.g. Ephestia, Mamestra, Earias, Pectinophora, Ostrinia, Trichoplusia, Pieris, Laphygma, Agrotis, Amathes, Wiseana, Triporysa, Diatraea, Sporganothis, Cydia, Archipso, Plips, Helipso, Plips, Plips Spodoptera or Tineola spp.), Diptera (e.g. Musca, Aldes, Anopheles, Culex, Glossina, Simulium, Stomoxys, Haematobia, Tabanus, Hydrotaea, Lucilia, Chrysoma, Callitroga, Dermatobia, Gasterophilus, Hypoderma Aryma, Hylem , Ceratitis, Liriomyza and Melophagus spp.), Phthiraptera (Malophaga, e.g. Damalina spp. And Anoplura spp. E.g. L inoghathus and Haematopinus spp.), Hemiptera (e.g. Aphis, Bemisia, Phorodon, Alneomalia, Empoasca, Parkinsiella, Pyrilla, Aonidiella, Coccus, Pseudococus, Helopeltis, Lygus, Dysolercus, Oxycarenus, Megara, Nezara, Nezra , Phylloxera, Adelyes, Nilopavata, Nephrotetix or Cimex spp.), Orthoptera (e.g. Locusta, Gryllus, Schistocerca or Aeluta spp), Dictyoptera (e.g. Blatella, Periplaneta or Blatta spp.), Hymenoptalia, Ceus, e.g. , Solenopsis, Monomorium spp.), Isoptera (e.g., Odontotermes and Reticulitermes spp.), Siphonaptera (e.g., Ctenocep-halides or Pulex spp.), Thysanura (e.g., Lepisma), Dermaptera (e.g., Forficula), Pscocustera and Thysanoptera (Thrips tabaci).

 Acaricidal insects include members of the genera, Haemaphysalis, Dermacentor, Anocentor, and ticks and itching insects such as Acarus, Getranychus, Psoropter, Notoednes, Sarcoptes, Psorer-gates, Chorioptes, Eutrombicula, Demodex, Panonychus, Bryobiaula, Bryobia Polyfes, Bryobia polyphys, Scutigerella, Oniscus spp.

 Nematodes that infect plants and trees that are important for agriculture, forestry, horticulture either directly or by spreading bacterial, viral, mycoplasmic or fungal diseases of plants include root nematodes such as Meloidogyne (e.g. M.incognita), cyst-forming nematodes such as Globodera (e.g. G.rostochiensis), Heterodera (e.g. H.avenae). Radopholus (e.g. R. similis), damaged nematodes such as Pratylenchus (e.g. P. pratensis), Belonolaimus (e.g. B. gracilis), Tylenchulus (e.g. T. semipenetrans), Rotylenchulus), R. reni-formis, Rotylenchus (e.g. R.robustus), Helicotylenchus (e.g. H.multicinctus), Hemicycliophora (e.g. H. gracilis), Criconemoides (e.g. C. similis), Trichodorus (e.g. T.primitivus), Xiphinema (e.g. X.diversicandatum), Longidorus (e.g. L. elongatis), Hoplolaimus (e.g. H. coronatus), Aphelenchoides spp. (e.g. A.ritzema-bosi), A.besslyi, as well as stem and bulb nematodes, such as Ditylenchus (e.g. D.dipsaci).

 The compounds of the present invention may be combined with one or more other pesticidal active components (e.g., pyrethroids, carbamates and organophosphates) and / or attractants, repellents, bactericides, fungicides, non-methocides, anthelmintics and the like. In addition, the activity of the compounds of the present invention can be enhanced by the addition of a synergist or potentiator, for example one of the class of synergist oxidase inhibitors, such as piperonyl butoxide or propyl 2-propynyl phenyl phosphonate, the second compound of the invention or the pesticidal pyrethroid compound. When an oxidase inhibitory synergist is present in the claims, the ratio of the synergist to the compound of formula (1) is 25: 1-1: 25, for example 10: 1.

 Stabilizers to prevent any chemical degradation that may occur with the compounds of the present invention include, for example, antioxidants (such as tocopherols, butylhydroxyanisole and butylhydroxytoluene) and absorbents (such as epichlorohydrin) and organic or inorganic bases, such as trialkylamines can act as a base stabilizer and as an absorber.

 The compounds of formula (1) included in the pesticidal composition according to the present invention are presented in tables 1-4.

 Compositions, wt.

2. Смачиваемый порошок
Соединение фор-
мулы (1) 25,00
Аттапульгит 69,50
Изопропилбен-
золсульфонат
натрия 0,50
Натриевая соль
конденсированной
нафталинсульфо-
кислоты 2,50
Бутилированный
окситолуол 2,50

3. Дуст (порошок)
Соединение фор-
мулы (1) 0,50
Бутилированный
гваякол 0,10
Тальк 99,40

4. Приманка
Соединение фор-
мулы (1) 40,25
Ледяной сахар 59,65
Бутилированный
окситолуол 0,10

5. Лак
Соединение фор-
мулы (1) 0,1
Бутилат пиперо-
нила 0,5
Бутилированный
гваякол 10,1
Высокоаромати-
ческий уайт-спирит 92,0

6. Аэрозоль
Соединение фор-
мулы (1) 0,30
Бутилированный
гваякол 0,10
1,1,1-трихлорэтан 4,00
Непахнущий
керосин 15,60
Арктон 11/12,
50:50 смесь 80,00

7. Спрэй (раствор для опрыскивания)
Соединение фор-
мулы (1) 0,1
Бутилированный
гваякол 0,1
Ксилол 10,0
Непахнущий
керосин 89,8

8. Спрэй с усиливающим действием
Соединение фор-
мулы (1) 0,1
Бутилат пипе-
ронила 0,5
Бутилированный
гваякол 0,1
Ксилол 10,1
Непахнущий
керосин 89,2

Активность соединений предлагаемого изобретения испытывали при растворении заявленных соединений в ацетоне (5%), а затем разведении полученного раствора в смеси вода: Synperonic (94,5%0,5%) для получения водной эмульсии. Указанный раствор используют для обработки следующих вредителей-насекомых.1. Emulsifiable concentrate
Compound for
mules (1) 10.00
Ethylan KEO 20.00
Xylene 67.50
Bottled
guaiacol 2.50

2. Wettable powder
Compound for
mules (1) 25.00
Attapulgite 69.50
Isopropylben-
zolsulfonate
sodium 0.50
Sodium salt
condensed
naphthalenesulfo-
acid 2.50
Bottled
oxytoluene 2.50

3. Dust (powder)
Compound for
mules (1) 0.50
Bottled
guaiacol 0.10
Talc 99.40

4. The bait
Compound for
mules (1) 40.25
Ice sugar 59.65
Bottled
oxytoluene 0.10

5. Varnish
Compound for
mules (1) 0.1
Butylate piper
nile 0.5
Bottled
guaiacol 10.1
High aromatic-
White Spirit 92.0

6. Aerosol
Compound for
mules (1) 0.30
Bottled
guaiacol 0.10
1,1,1-trichloroethane 4.00
Odorless
kerosene 15.60
Arcton 11/12,
50:50 mix 80.00

7. Spray (spray solution)
Compound for
mules (1) 0.1
Bottled
guaiacol 0.1
Xylene 10.0
Odorless
kerosene 89.8

8. Strengthening spray
Compound for
mules (1) 0.1
Butylate Pipe
dropped 0.5
Bottled
guaiacol 0.1
Xylene 10.1
Odorless
kerosene 89.2

The activity of the compounds of the invention was tested by dissolving the claimed compounds in acetone (5%), and then diluting the resulting solution in a mixture of water: Synperonic (94.5% 0.5%) to obtain an aqueous emulsion. The specified solution is used to treat the following insect pests.

Musca domestica. 20 females are placed in a cardboard cylinder with a net on both sides. A solution containing the test compound is sprayed onto the insect through a wire mesh. After 48 hours at ²⁵ ° C the mortality assessed.

 The following compounds exhibit activity at less than 1000 ppm. 4,5,14, 20,21,22,24,24,25,26,28,32,43,44,45,50,53, 54,56,69,71,72,76, 77,82, 88.89.

 The following compounds exhibit pesticidal activity at less than 200 ppm. 6,9,10,11,12,13,15,16,17,29,30,31,33,34,46,47,48,52,57,58,59,60,61,62,63, 64.65.68.74.75.78, 79, 79.80.81.83.84.85.90.

Sitophilus granaris and Gribolium castaneum. 20 adults of Sitophilus and Gribolium are added to 10 g of wheat, the grains of which are pre-treated with 2 ml of a solution containing the proposed compounds. Mortality rate after 6 days at 25 ^about C.

 The following compounds exhibit pesticidal activity against Sitophilus granaris at less than 1000 ppm. 7,10,19,22,23,25,26,27,32,43,44,50,56,69,82, 85,89,90. The following compounds are active against Sitophilus granaris at a flow rate of less than 200 ppm. 3,4,5,6,9,12,14,15,16.17,29,30,31,33,34,45,47, 48,53,54,57,58,60, 61,62,68, 72.74.75.76.77.78, 79.80.61.

 The following compounds exhibit activity against Gribolium castaneum at a dose of less than 1000 ppm. 4,6,10,14,17,33,53, 57,58,65,71,76,79,79,82,84.

 The following compounds are active as pesticides against Gribolium castaneum at 200 ppm. 9,12,15,16,34,46,63,74,75.

Myzus persical. 10 adults of Myzus are placed on a plate of a leaf of Chinese cabbage. After 24 hours, the leaf blade is sprayed with a solution containing the test compound. Mortality rate after 2 days at 25 ^about C.

 The following compounds exhibit pesticidal activity at a dose of less than 1000 ppm. 4,9,17,37,46,53,56,60,71,77,78, 79,80,81,84.

 The following compounds exhibit pesticidal activity in a dose of less than 200 ppm. 6.45.47.48.57.58.59.62.53.74.75.76.

Plutella xylostella. 7 Plutella larvae are sprayed with a solution containing the test compound and placed on a leaf of Chinese cabbage, which is similarly sprayed with the test compound and allowed to dry. Alternatively, 9-10 Plutella larvae are placed on leaf blades and sprayed with a solution containing the test compound. The mortality rate is calculated after 2 days at 25 ^about C.

 The following compounds exhibit pesticidal activity at less than 1000 ppm. 15,16,25,29,31,33,34,35,48,55,56,58,59,65,68,71,75,77,78,79,80,81,83,85,87.

 The following compounds exhibit activity at a dose of less than 200 ppm. 9,12,13,46,47,57,74.

Getranychus urtical. Leaf plates containing a mixed Getranyclues urtical population are sprayed with a test compound solution. Mortality was assessed after 2 days at 25 ^C. The following compounds were active at a dose of less than 1000 hr. / Mlg. 78.81.83.90.

 The following compounds exhibit pesticidal activity in a dose of less than 200 ppm. 60.80.

Additional tests for the action of a spray solution. The pesticidal activity of the compounds of the invention was investigated further. The compounds are dissolved in acetone (75%) and then water is added. The specified solution is used for spraying the following pests:
Aphis fabae. A mixed population of Aphis fabae was tested on nasturtium leaves.

 The following compounds exhibit pesticidal activity at a dose of less than 1000 ppm. 4,6,13,16,17,25,26,29,30,31,33, 46,47,50,54,63,65.

 Macrosteles fascifrons.

 Adult Macrosteles fascifrons were tested on wheat germ.

 The following compounds exhibit activity at a dose of less than 1000 ppm. 6.9,13,16,17,23,25,26,29,31,33,34,46,47,63,65,68.

 Getranychus certical. A mixed Getranychus urtical population was tested on legume leaves. The following compounds exhibit activity at a dose of less than 1000 ppm. 5.9,16,30,33,31,46,47,50,65,68.

 Diabrotica undecimpunctata in the third stage of development is tested on filter paper.

 The following compounds exhibit pesticidal activity at a dose of less than 1000 ppm. 3,4,5,6,13,16,17,23,25,26,29,30,31,33,34,46,47,53,63,65,68.

 The activity of the proposed compounds against the non-anesthetized female of the Musca domestica common fly (WRL line) is indicated for topical application of a solution containing the test compound and piperonyl butylate in butanone to the insect tested. Mortality is assessed after 48 hours.

 The following compounds exhibit pesticidal activity at a dose of 1 μg: 9,10,11,12,13,15,17,29,30,31,33,34,47,52,63, 64,68,83,84,85.

 The activity of the proposed compounds against the anesthetized male Periplaneta americana was demonstrated by topical application of a solution containing the test compound in butanone to the insect tested. Mortality is assessed after 6 days.

 The following compounds exhibit activity in a dose of less than 50 μg: 2,6,16,17,25, 31,39,83.

 The pesticidal activity of the compounds against the anesthetized male Blattella germanica was demonstrated by topical application of a solution containing the test compound in butanone on an insect tested.

 Mortality is determined after 6 days.

 The following compounds exhibit pesticidal activity in a dose of less than 5 μg: 6.9,12,14,15,16,17,20,29,30,31,33,34,45,46,48,56,57,58,59 , 60.61.62.63.65.66, 67.774.75.83.84.90.

 Nematicidal activity.

 Meloidogyne incognita. Selected compounds of the invention were analyzed on the newly hatched nematode Meloidogine incognita 2. The test solution contains a mixture of 1% acetone with 100 ppm Triton X-100. Nematicidal activity determined after 24 hours

 The following compounds exhibit activity in a dose of less than 100 ppm. 6,16,17,26.

 The toxicity of the proposed compounds was established by oral intubation of a Charles RiverCPL mouse fasting for 3 hours. The test compounds were administered as solutions in DMSO at a dose of 200 mg / 10 ml / kg, 20 mg / 10 ml / kg and 2 mg / 10 ml / kg. Toxicity is determined 14 days after administration.

The following ratios are toxic with an LD _{50 of} 200 mg / kg ^-1 : 17.60.

The following compounds exhibit toxicity with LD ₅₀ in the range of 20-200 mg / kg ^-1 : 16.75.

 The results of comparative tests of the compounds of the present invention are presented in table.5.

Table 5 gives the following notation:
Di Diabratica undecimpunctata (long-lipped flea);
Ma Macrostiles fascifrans (circadian);
Ap Aphis fabal (aphid bean);
Tu Getranychus urtical (two-spotted spider mite);
Sg Sitophilus granarius adults (calendaring);
Tc Gribolium castaneum adults (mealworm);
Px Plutelia xylostella larvae (cabbage moth);
Mp Myzus persical adults (aphid peach);
Bg Blattella hermanica adults (red cockroach);
Md Musca domestica adults (housefly)
U is not synergized by piperonyl butoxide.

 Typically, tests on Blattella are not synergized and tests on Musca are not synergized.

Claims (3)

1. INSECTOACARICIDAL COMPOSITION, comprising the active ingredient - a derivative of bicyclooctanes and target additives, characterized in that as a derivative of bicyclooctane it contains a compound of the general formula

where R is n.propyl, tert.butyl;
R ¹ is hydrogen, trifluoromethyl, cyano;
.R ² is hydrogen;
AX is hexynyl, butynyloxymethyl, 3, 3-dimethylbutyl, 4-ethynylcyclohexyl;
Y and Y ¹ have the same values selected from oxygen and sulfur;
Z is CH ₂ O, CH ₂ S,
with the following ingredients, wt.%:
Bicyclooctane derivative - 0.1 - 40.25
Targeted Supplements - Else
2. The composition according to claim 1, characterized in that it further comprises piperonyl butylate in an amount of 0.5 wt.%. 3. The composition according to p. 1, characterized in that it contains a compound of the formula 1, according to claim 1, where R is n.propyl, tert.butyl;
R ¹ is hydrogen, trifluoromethyl, cyano;
R ² is hydrogen;
AX is hexynyl, butynyloxymethyl, 3, 3-dimethylbutyl, 4-ethynylcyclohexyl;
Y and Y ¹ have the same values selected from oxygen, sulfur;
Z is CH ₂ O, CH ₂ S. 4. The composition according to p. 1, characterized in that it contains a compound of formula 1 according to claim 1, where R is n.propyl, tert.butyl;
R ¹ is hydrogen, cyano;
R ² is hydrogen;
AX - hexynyl,
Y and Y ¹ have the same values selected from oxygen and sulfur;
Z - CH ₂ O.

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