TW200902505A - Insecticidal derivatives of substituted phenylalkylamines - Google Patents

Abstract

The present invention relates to novel derivatives of substituted phenylalkylamines, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects.

Description

200902505 IX. DESCRIPTION OF THE INVENTION: TECHNICAL FIELD OF THE INVENTION The present invention relates to insecticidal derivatives of novel substituted phenylalkylamines, methods for their preparation, and their use for controlling animal pests, particularly arthropods 5 The use of objects, especially insects. A benzylamino heterocyclic derivative of the insecticidal and arachnid of the following general formula is disclosed in WO 2006/127426 as a specific example (see, for example, Formula IB, page 8) r2 R\

R R--N=/ R1 10 wherein R is 1-naphthyl, phenyl or phenyl substituted by one or two selected from halogen or (CrC2)alkyl; R1 is selected from hydrogen, (Ci-Q) Alkyl and (CrC2)haloalkyl; R2 is hydrogen; R5 is selected from cyano, (CVC2) alkoxy (CrC2) alkyl, 4-(CrC2) alkoxy-15-benzyl, R\X R10 0 X II -P; —C-0-^—R11 II -N-R13 R14 X Η (1) (3) (5) X —Sx(〇)a II -R16 —c: Η二N—R19 (6) (7) ( 9) 200902505 where

X 5 :: or ^ R and R are (Ci_C2) alkoxy or (Ci_C2)-alkyl; r10 di/((VC4) alkyl; Rl3 is (Cl-C2) alkyl; Rl4 is hydrogen or two thereof Ff ; a 4 2 ; Rl5 is (cc picking base: ): 2) second compound base amine di-glycine:,, (Cl-C2) fluorenyl or (Ci_C2) alkoxy; and R19 is (CVC2) alkane Or a (Ci-Q) alkoxy group; f is a naphthyl group and R5 is a formula (5) (wherein X is sulfur, R13 is methyl and is stupid and wind is ((YC2)) excipient; and R is 3-gas-2-indenyl 10:, when it is hydrogen, R is a formula (5) (wherein X is oxygen, R13 is sulfhydryl and rm ', , wind) or formula (6) (where 2 and 5 is methyl) except for a. However, there is a need for an insecticide and arachnid which is not only safer than the known compounds, but also more suitable for the new head. Novel compounds of formula (I) are now available

R7 (1) 15 wherein R _R and R independently of each other represent hydrogen, halogen, thiol, alkyl, alkoxy, iialkyl, alkoxyalkyl, cycloalkyl, cyanoalkyl, _alkoxy, Alkylthio, ialkylthio, alkylsulfonyl, alkylsulfonyloxy, haloalkylsulfonyl, haloalkylsulfonyloxy, alkoxycarbonyl, ethylidene, 20 alkane Carbocarbonyl, alkenylcarbonyl, pentafluorosulfonyl, amine, mono- and dialkylamine 6 200902505 ίο 15 20, cycloalkylamine, alkenyl, ethenyl, block, halo, cyano Or an aryl group, or independently of each other, an aryl, aryloxy or heteroaryl group optionally having one or more selected from the group consisting of halogen, alkyl, dentate, alkoxy, alkoxy, and oxygenated Substituents of a carbonyl group, a nitro group and a cyano group are substituted. Representing an alkyl group, a halogen group, a cycloalkyl group, an alkoxy group, an alkyl group, an alkenyl group or a fast group, or an aryl group or a heteroaryl group. a radical (tetra)yl or a heterocyclic group, optionally or a plurality selected from the group consisting of ", fluorene, and fluorenyl 1 substituted; representing hydrogen, alkyl or haloalkyl; representing -C(Z)R1() , -QZPR1. , -C(Z)Nrhr12 or _p(z)rI3r14 represents hydrazine or s; ' represents CVC2 alkyl; represents crc2 alkyl; represents hydrogen or crc2 alkyl; and Rl3 and R14 each represent Cl-C: 2 alkoxy a group or a CrC2_alkoxy group; the C-atom substituted by an island with R6 is asymmetric or palm-shaped and the compound of formula (1) is photoactive: active. A molecule whose mirrors do not overlap is called a palm; if these molecules are optically active, if the image is not heavy, the mirror must be a different molecule because the overlap is equivalent to the same. In each case of the optical activity of a pure compound, there are two and only two isomers, called photoisomers, which differ structurally only in their orientation from the left-hand side to the right-hand side. Mirroring isomers differ in that they rotate polarized light in opposite directions and that they react at different rates with other palm compounds or in the presence of a palmizer (see March High Order Organic Chemistry 5th) Edition; Wiley 2001, pp. 125-126). R6 R7 R8 Z R10 R11 R12 7 200902505 Asymmetric carbon atom can be based on the Cahn-Ingold-Prelog system in which four groups on asymmetric carbon atoms are arranged in descending order of atomic number. - or R-configuration exists (see March, Higher Order Organic Chemistry, Edition; 2001, page 139). 5 Depending on the successor substituent r1 to r6, the 'asymmetric carbon atom' exists in the R- or S-configuration. Compounds with limited rotation may have cis-trans isomerism. One type of cis-trans isomerism is caused by a double bond, such as N = 噚 咬 _ _ double bond. According to the Kang-Inge-Pilo system, which is arranged in the order of decreasing atomic number on the atoms of the double bond 10, the compound according to the invention may exist in Z or E form, and the z shape is in the double bond Isomers with two higher alignment groups on the same side (see March, Organic Chemistry, 5th Edition; Wiley 2001, pp. 157-158).

The novel compound of formula (1) of the present invention is not disclosed or suggested in WO2006/127426. In particular, it is not disclosed or suggested in WO2006/127426 that the compounds of formula (1) are superior to their optical mirrors or racemates in surprisingly significantly improved killing activity. As used herein, an "optical mirror image" of an S-mirror isomer is defined as an R-mirror isomer corresponding to 8 20 200902505, which differs only in the configuration of the c_atom of the rotationally polarized light in the opposite direction and In the corresponding S-mirror = thus the optical mirror of the R-mirror isomer 5 (I) provides a general definition of the compound of the invention. See below. Preferred substituents or ranges for the groups given in the formulas described herein, according to another preferred embodiment of the invention, /() RRR, R and r5 independently of each other represent hydrogen, halogen (preferably 10 ^ domain), thiol, fluorenyl (preferably CA alkyl), Cl_C4 (CrC2 alkoxy), crc4 haloalkyl (preferably Ci_c2: hospital base), (crc4); ^oxy (CrC4) filament (preferably (Ci_c2) oxy-oxygen = (Cl-C2) alkyl), C3-C8 cycloalkyl (preferably c3-c6 cycloalkyl), cyanide, (Crc4) Base (preferably chloro (Ci_c2) alkyl), i& (Ci_C4) 15 alkoxy (preferably dentate (Cl-C2) alkoxy), CrC4 thiol (preferably CVQ alkyl sulphide) Alkylthio (preferably halo (Ci_c2) t alkylthio), CrC4 alkylsulfonyl (preferably Ci_c2 alkylsulfonyl), C1-C4 alkyl Sulfhydryloxy (preferably ^-alkylsulfonyloxy), halogen (CrC4) alkylsulfonyl (preferably alkylsulfonyl), halogen (CrC4) alkylsulfonyloxy Base (preferably halo(crc2)alkylsulfonyloxy), CrC4 alkoxycarbonyl (preferably Ci_c2 alkoxycarbonyl), ethylidene Cl_C4 alkylcarbonyl (preferably G-C2 alkylcarbonyl), c2-c4 alkenylcarbonyl, pentafluorosulfonyl, amine, mono- and di(Ci_C4)alkylamino (preferably mono- and di-) (CrC2)alkylamino), c3_Cs cycloalkylamino (preferably 〇3-0:6 cycloalkylamino), C2-C4 alkenyl, j(c2_C4), c2_c4 alkynyl, 9 200902505 5 , a group (cvao fast radical, cyano or sulfo group, or independently of each other represents c _c 3 C preferably cvc6 aryl), C5_C8 aryloxy (preferably ^ square milk) < 5-8 member ring included a heteroaryl group comprising i, 2 or more hetero atoms of k, oxime, N, P and S, optionally having one or more selected from the group consisting of halogen, CrQ alkyl (preferably Crc2) Halogen (c (, preferably harc (crc2) filament), Ci_Q alkoxy (preferably alkoxy), halo (crc4) alkoxy (preferably halo (Ci_D decyloxy, CrC4) Alkoxycarbonyl (preferably a substituent of the Ci_C2 alkoxycarbonyl group 四(tetra)); ^ represents a Qq alkyl group (preferably a Ci_C2 alkyl group), and Ci_C4 is a hospital group (preferably a CA halogen group), ^cycloalkyl (preferably & cycloalkyl), (cvc4) alkoxy (Cl_C4) alkyl (preferably (Ci_C2) burned Yl (q_C2) burn-yl), CVC4 burning thiol group (Ci_c4) burning group (preferably to a thiol group (CRC2) burn-yl), c2-c4 C2_C4 alkenyl or alkynyl group, or on behalf;

a Cs-C8 aryl group (preferably a Cs-C6 aryl group), a heteroaryl group comprising a 5-8 membered ring, which comprises 1, 2 or more heteroatoms selected from the group consisting of ruthenium, N, p&s, i-selective One or more selected from the group consisting of i-, CrC4 alkyl (preferably CrC2 alkyl),

a substituent of a Crh alkoxy group (preferably Cr(:2 alkoxy), a nitro group and a cyano group is substituted; 20 R represents hydrogen, a CrC4 alkyl group (preferably a CrC2 alkyl group) or a Cl_c4il alkyl group (more Preferably, crc2 ii alkyl); R represents _C(Z)Rl〇, _C(z)〇R10, -C(Z)NRUR12 or -P(z)R13R14; z represents o or s;

RlQ represents CVC2 alkyl; 200902505 R11 represents CrC2 alkyl; R represents hydrogen or crc2 alkyl; and R and R each represent Ci-C2 alkoxy or C1-C2 halooxy. As used herein, "alkyl" is defined as a straight or branched alkyl group, such as fluorenyl, ethyl, n- or i-propyl, n-, i-, second or third. Butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-decyl, n-undecyl, n-undecyl, etc. are preferably Cw alkane More preferably, it is a Ci 4 alkyl group. 10 "Alkenyl" is defined as a straight or branched C212 alkenyl group containing at least one double bond, such as ethenyl, propenyl, fluorenyl-propenyl, isopropenyl, propenbutyl, 2 diphenyl, 3_butyl, hydrazine, 3-butadienyl, pentyl, 2-pentenyl, 3-j alkenyl, 4-pentenyl, 1,3 pentadienyl, hexenyl, 2 _ hexenyl, 3-hexenyl, 4-hexenyl, 5-hexyl, M-hexadienyl, etc., preferably Gy, particularly preferably C2_4 alkenyl, most preferably Ci_c2 base. 15 "Alkynyl" is defined as a c2-12 alkynyl group containing at least one triple bond and optionally further comprising one or more double bonds, such as an ethynyl group, a L-propyl block group, preferably a c2-6 alkynyl group, particularly preferably C24 alkynyl. "2" "Oxygen", "Silicon", "Pure Money", "Fujiji", "F-Amine", "(A)oxy", "Alkoxy" The part of the silk, such as "the hospital oxygen prison base" y alkoxy county silk, and 20 parts. k h lane"; it is defined as & cycloalkyl group such as cyclopropyl, cyclobutyl, hetero Si ί 'cyclooctyl #, preferably ^ ring group. It is defined as a ring-containing group containing 5-8 tributary rings. 2 or more heteroatoms selected from 〇, n, ms, such as four 11 200902505 hydroquinone, tetrahydroanthracene Phenyl, pyridine, oxathiolan, oxime, tetrahydrofuran, piperidine, bisaki, etc., preferably tetrahydrofuran. "Aryl" is defined as saturated A C5-C12 cycloalkyl group such as phenyl, α- or β-naphthyl, preferably phenyl. 5 "Heteroaryl" is defined as an aryl group containing a 5-8 membered ring containing 1, 2 or more heteroatoms selected from the group consisting of ruthenium, osmium, iridium and S, such as furan, thiophene, pyroline, π 0 sitting, α plugging, π than 嗤,. Than σ,. Density σ, π ratio σ sitting, etc., preferably π π and σ 毕 洛. The "aralkyl group" is defined, for example, as a benzyl group, a phenethyl group or an α-mercaptobenzyl group, and more preferably a benzyl group. 10 "Halogen" is defined as fluorine, gas, bromine or iodine, preferably fluorine or chlorine. As a "halogen-based group", "halogen-burning oxy group", "halogen-sintering thio group", "halogen-burning sulphur-based sassafrasyl", "haloalkylsulfonyloxy", "haloalkenyl", "haloalkynyl" The halogen portion of the etc. is as listed above. According to a particularly preferred embodiment, R1, R2, R3, R4 and R5 of the formula (1) independently of each other represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, alkoxyalkyl, bad alkyl, 13⁄4 Alkoxy group, beaker base, halogenated sulfur group, pyridyl fluorinyl group, pyridyl fluorenyloxy group, halogenated fluorenylxanthyl group, alkoxycarbonyl group, ethyl fluorenyl group, alkylcarbonyl group, alkenylcarbonyl group, Alkylamino, cycloalkylamino, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cyano or 20 wall; R6 represents alkyl, dentate, cycloalkyl, alkoxyalkyl, alkane a thiolalkyl, alkenyl or alkynyl group, or an aryl group, optionally substituted with one or more substituents selected from halogen; R7 represents hydrogen or alkyl; 12 200902505 R8 represents -C(0) R10, -C(0)OR10, -C(S)NRUR12 or _p(8)rur14. Riq represents CVC2 alkyl; 'R11 represents crc2 alkyl; R represents murine or C1-C2 alkyl; and R and R each represent 匚广匚2 alkoxy or Ci-C2 halogen alkoxy. Ίο 15 20 According to one of the special examples of the above-defined definitions, the compound of formula (1), 1, 12, 113, 114 and 115 independently represent hydrogen and 2 (preferably gas or fluorine). ), acrQ alkyl group (preferably Cl_C2 alkyl group), a Ci_c4 alkyl group (preferably Ci-C: 2 alkoxy group), a CVC4 halogen group (preferably a c^c halogen group), (CrC4) Alkoxy (CrC4) alkyl (preferably (Ci_c2) alkoxy (CrC2) alkyl), CVC8 cycloalkyl (preferably C3_c6 cycloalkyl), halo (CrC4) alkoxy (comparative) Preferably, it is a aryl group (Cl_c2) alkoxy group, a Cl-c alkylthio group (preferably a CVC2 alkylthio group), a functional group (CrC4) disulfide group, and a halogen group (C^C: 2). Sulfhydryl), CrC4 alkylsulfonyl (preferably C) _C2 alkylsulfonyl), CrC4 alkylsulfonyloxy (preferably Ci_C2 alkyl 2 fluorenyloxy), halogen (CrC: 4) alkylsulfonyl (preferably alkylsulfonyl), crc4 alkoxycarbonyl (preferably Ci_C2 alkoxycarbonyl), ethylidene, CrC4 alkylcarbonyl (preferably Ci_c2) Alkylcarbonyl), Q-C4 alkenylcarbonyl, bis(CKC4)alkylamino (preferably di(Ci_c2)alkylamino), CV C8 cycloalkylamino group (preferably CVC6 cycloalkylamino), C2_C4 alkenyl, halogen (c2-c4), c2_c4, dentate (6), fast, cyano or nitro; R6 represents crc4 An alkyl group (preferably a Cl_c2 group), a Ci_C4 dentate group (preferably a crC2 dentate group), a C3_Cs cycloalkyl group (preferably a c3_c6 cycloalkyl group), 13 200902505 5 10 (crc4) alkoxy group ( CrC4 is a base (preferably (Ci_c oxyalkyl), crc4 thiol (CVC4), (C), (c), c2_C4 thiol or C2_C4*, Is a cva aryl group, optionally substituted with - or a plurality of substituents of a halogen; represents hydrogen, a CrQ alkyl group (preferably a Ci_C2 alkyl group); represents -C(9)Rio, _C(O)〇Rl0, a moiety亮 ll Rl 2 or represents Crc 2 alkyl; UK ' represents CVC 2 alkyl; represents hydrogen or CrC 2 alkyl; and R and 尺 14 each represent C _C 2 alkoxy or crc 2 halo oxy. According to an excellent embodiment of the invention , (I), 2, 3, 3, and 5 independently of each other represent hydrogen, halogen, alkane, alkoxy or haloalkyl; represents an alkyl or adentate alkyl group, or represents an aryl group, Selective one or more Substituted from a halogen substituent; represents hydrogen; represents -C(0)R10, _C(0)〇R10, _c(S)NRuR12 or -P(S)R13R14; represents crc2 alkyl; represents crc2 alkyl; Representing hydrogen; and 13 R and R 14 independently of each other represent an oxy group. A compound of a particular group according to one of the excellent specific examples defined above, R1, R2, R3, & 4 and R5 of formula (I) independently of each other represent hydrogen, halogen (轼铗R7 R8 Rio R11 R12 13 15 R6 20 R7 R8R10 Ru R12 14 200902505 is chlorine or fluorine), CrC4 alkyl (preferably Cl_C2 alkyl), Ci_C4 alkoxy (preferably CrC2 alkoxy), crC4 halogenated (preferably c halogen) Alkyl); 1 2 R6 represents Cr (:4 alkyl (preferably Ci_C2 alkyl) or Ci_C4 haloalkyl (more preferably Cl_C2 haloalkyl), or CVC8 aryl (preferably (:^)仏aryl), optionally substituted by one or more substituents selected from dentate; r7 represents hydrogen; R8 represents ·C(〇)R10, _C(〇)〇R1〇, _c(s)nr11r12 or p(3)r13r14 R1() represents a crc2 alkyl group; 10 R11 represents a CrC2 alkyl group; R12 represents hydrogen; and R13 and R14 each represent (^-(^ alkoxy group. According to a preferred embodiment of the invention, R1 of the formula (I) , R 2 , R 3 , R 4 and R 5 independently of each other represent hydrogen, halogen, alkyl, 15 decyloxy or alkoxy; R 6 represents an alkyl group; R 7 represents hydrogen; r 8 represents -c(s) nrur12 or -p(s )r13r14 ; R11 stands for CVC 2 alkyl; 20 R12 represents hydrogen; and R13 and R14 independently of each other represent CVC2 alkoxy. A special group of compounds according to one of the best definitions defined above, R1, R2, R3, R4 and R5 of formula (1) Respectively, independently of each other, hydrogen, halogen (preferably gas or fluorine), C1-C4 alkyl (preferably Ci-C2 alkyl), Ci_C4 oxygenated 15 200902505 (preferably Q-C2 alkoxy), crC4 haloalkyl (preferably C1_C2 haloalkyl); R6 represents crc4 alkyl (preferably crc2 alkyl); R7 represents hydrogen; 5 R8 represents -C(S)NRnR12 or -P(S)R13R14; R11 Represents a crc2 alkyl group; R12 represents hydrogen; and R13 and R14 independently of each other represent an oxy group. As another specific example, the present invention provides a novel compound of formula (lb), ie, a racemic mixture of a compound of formula 10 (I),

Wherein R1, R2, R3, R4 and R5 independently of each other represent hydrogen, halogen, hydroxy, alkyl, 15 alkoxy, haloalkyl, alkoxyalkyl, cycloalkyl, cyanoalkyl, i alkoxy Alkylthio, haloalkylthio, alkylsulfonyl, alkylsulfonyloxy, haloalkylsulfonyl, haloalkylsulfonyloxy, alkoxycarbonyl, ethylidene, An alkyl group, an alkenyl group, a pentafluoro group, an amine group, a mono- and a diammonium group, a cycloalkylamine group, an alkenyl group, an alkenyl group, a fast group, a fast-acting group, a cyano group or a nitrate a group of 20, or independently of each other, representing an aryl, aryloxy or heteroaryl group having a selectivity of 16 200902505 via one or more selected from the group consisting of halogen, alkyl, dentate, alkoxy, alkoxy, alkane The substituents of the oxycarbonyl group, the nitro group and the cyano group are substituted; preferably, R1, R, R, R and R independently of each other represent hydrogen, _, calcin, alkoxy or haloalkyl; At least one of R1, R2, R3, R4 and R5 is 5 hydroxy, alkoxy, _alkyl, alkoxyalkyl, cycloalkyl, cyanoalkyl, haloalkoxy, alkylthio, || Alkylthio, alkylsulfonyl, alkylsulfonyl , haloalkylsulfonyl, t-alkylsulfonyloxy, alkoxycarbonyl, ethenyl, alkylcarbonyl, alkenylcarbonyl, pentafluorosulfonyl, amine, mono- and dioxane An amine group, a cycloalkylamino group, an alkenyl group, a alkenyl group, an alkynyl group, an alkynyl group, a 1 fluorenyl group or a nitro group, or an aryl group, an aryloxy group or a heteroaryl group, the selectivity of which is one or more Substituents selected from the group consisting of a ruthenium, an alkyl group, an alkyl group, an alkoxy group, a halogen alkoxy group, a 6 alkoxycarbonyl group, a nitro group and a cyano group are substituted; R represents an alkyl group, a halogen group, a ring burn a base, an alkoxyalkyl group, a thiol thiol group, an alkenyl group or a aryl group, or an aryl group, a heteroaryl group or a heterocyclic group, optionally selected from - or a plurality selected from dentate a substituted alkoxy group, an alkoxy group, a decyl group and a cyano group; preferably, R6 represents an alkyl group or an i-ray, or an aryl group, the selectivity of which is substituted by halogen; ^ represents hydrogen, an alkyl group or a Preferably, R7 represents hydrogen; 20^ represents -C(Z)Rl°, ^1. , _C(Z)NRUr12 or -P(Z)r13r14; 20 Z represents Ο or S;

Rl() represents a Ci-C2 alkyl group; RU represents a CVC2 alkyl group;

Rl2 represents hydrogen or a CrC2 alkyl group; and R independently of each other represents a Ci_C2 alkoxy group or a Ci_C2 halogenated alkoxy group. 200902505 As another specific example, the present invention provides a novel compound of the formula (Ib) wherein R1 5 10 15 R6 20 R7 R8 2 Rio R11 R2, R3, R4 and R5 independently of each other represent hydrogen, halogen, hydroxy, alkyl, Alkoxy, haloalkyl, alkoxyalkyl, cycloalkyl, cyanoalkyl, haloalkoxy, alkylthio, ialkylthio, alkylsulfonyl, alkylsulfonyloxy, Haloalkylsulfonyl, oxaalkylsulfonyloxy, alkoxycarbonyl, ethyl fluorenyl, alkylcarbonyl, alkenylcarbonyl, pentafluorosulfonyl, amine, mono- and dialkylamino, Cyclone, fluorenyl, fluorenyl, fluorenyl, chloro, cyano or trihydryl, or mutually depleted iL aryl, oxy or oligo, optionally having one or more selected from the group consisting of halogen and silk And (4) a base, an alkoxy group, a halogenated alkoxy group, a calcined 2 milk-based base group, a stone succinyl group and a cyano group substituent are substituted; preferably, r1, ^, R, R4 and -R5 each independently represent hydrogen, _素, 烧基,院氧:J-alkyl; premise, no more than two of r2, r3, r4 and r5 represent nitrogen, alkyl, alkoxyalkyl, alkylthiol η: Selected from, prime, alkyl, alkoxy, indeed And nitrogen-diyl group to be substituted, R represents an alkyl group or teeth to be burned halo substituent group〗 party 'through which intake Optional represents hydrogen, alkyl or haloalkyl; Preferably, R7 Representative -C ^ R1. , _C (Z) C) Rl. _ r11r12= ' 4 represents 0 or S; AP(Z)RR ' represents crc2 alkyl; represents crc2 alkyl; 18 200902505 5 10 R12 represents hydrogen or CrC2 alkyl; and R and R each represent Ci-C2 oxygenate Base or Ci-C] halogenated alkoxy group. As a further specific example, the present invention provides a novel compound of the formula (Ib) wherein R 2 , R 3 , R 4 and R 5 independently of each other represent hydrogen, halogen, hydroxy, alkyl, alkoxy, i-alkyl, alkoxyalkyl Base, cycloalkyl, cyanoalkyl, haloalkoxy, alkylthio, alkylthio, alkylsulfonyl, alkylsulfonyloxy, haloalkylsulfonyl, alkylsulfonyl Alkoxy, alkoxycarbonyl, ethyl fluorenyl, alkylcarbonyl, alkenylcarbonyl, pentafluorosulfonyl, amine, mono- and dialkylamino, cycloalkylamino, alkenyl, alkenyl, An alkynyl group, an alkynyl group, a cyano group or a nitro group or independently of one another represents an aryl group, an aryloxy group or a heteroaryl group, the selectivity, which is selected from the group consisting of dentate, alkyl, halogen, The substituents of the alkoxy group, the functional alkoxy group, the =oxy group and the cyano group are substituted; preferably, R1 and R independently of each other represent hydrogen, halogen, affiliation, alkoxy or ifi. $表%, group, alkoxyalkyl group, alkylthiolalkyl, alkenyl or alkynyl group, ^ represents a aryl group, an aryl group or a heterocyclic group, optionally via - or a plurality selected from halogen & And a substituent of a cyano group is substituted; preferably 2 represents an aryl group, which is selectively substituted by a functional group; a core 11'-alkyl group; preferably, r7 represents hydrogen; C(Z)R, _c(z)〇 Rl0, r11r12 3r14; represents 〇 or s; represents crc2 alkyl; represents crc2 alkyl; represents hydrogen or Ci-Q alkyl;

R 15 R6 R7 20 R8 Z R10 R11 R12 19 200902505 R13 and R14 each represent a CrC2 alkoxy group or a CrQ haloalkoxy group. The general or preferred group definitions or explanations given above apply to the product and the corresponding precursors and intermediates. These group definitions can be combined with one another as desired, including a combination of individual preferred ranges. 5 According to the invention, a compound of the formula (I) which comprises the above-mentioned combination of preferred meanings is preferred. Particularly preferred according to the present invention is a compound of the formula (1) which comprises a combination of the above-mentioned particularly preferred meanings. It is an excellent one according to the present invention to include the compound of the formula (1) which is a combination of the above. Preferred according to the invention is a compound of formula (I) which comprises a combination of the above in a best sense. The invention further relates to a composition comprising at least one compound of formula (I) as defined in any of the above specific examples, and conventional extenders and/or surface active agents. Conventional extenders and/or surfactants are defined as follows. The invention also relates to a method of controlling pests, wherein the compound of formula (I) as defined in any of the above specific examples, or at least one compound of formula (I) as defined in any of the above specific examples, and conventional extenders and / or a composition of the surfactant acts on the pests and / or their habitat. 20 A novel compound of formula (I) wherein R8 is -C(S)NRUR12 and R12 is hydrogen is a compound of formula (II) 20 200902505

R TN Λ NIH wherein R1, R2, R3, R4, r5, r6 and r7 are as defined above and a compound of formula (III)

Rn-NCS (III) wherein R11 is as defined above and N,N-main di-isopropyl acetyl-anthracene is in an aprotic solvent (such as dichloromethane, gas ίο; 丄二, 2 〇, depending The ratio obtained by the reaction under the solvent:; ===:=, compound: Further, in the formula (I), r8^c(s) nri1r12 and n. Also when R is a novel compound of hydrazine, a compound of formula (II)

H6 and R7 are as defined above

Ri, R2, R3, R4, R5, and thiododyldimoxide 21 15 200902505 s and the compound of formula (IV) r11-NH2 (IV) wherein 5 R is as defined above in a non-bei zizi agent (such as a chlorine In the case of methyl, chloroform, acetonitrile, dimethylformamide, tetrahydrofuran or ethyl acetate), it is obtained at a temperature of from 2 hr to i2 (r. preferably 〇 4 (rc, depending on the solvent). The reaction time is 丨 to 2 〇, the ratio of precipitates, the compound of formula II: thiocarbonyldiimidazole: the compound of formula m is i: 10 1 : 1 to 1: 2 : 2, preferably 1: u : u ( Method 2) The isocyanate of dextroamine is not commercially available (for example, aminoacetonitrile), and this method is preferred, and the corresponding amine itself can be used to shorten the synthesis route. In general, amine and thiocarbonyl are used. The synthesis of thiourea by imidazole reaction is known (see W〇2〇〇5/〇_卜, page 5 (4)). However, it is synthesized by reacting salivary with sulfur 15-based diimidazole and primary or secondary amines. Amino oxazolidine _3_ thioguanamine has not been previously disclosed. Surprisingly, it has been found that oxazolidine and thiocarbonyl dimiso and s- or secondary amines are found. It should be feasible. This is unpredictable for those skilled in the art due to the stagnation of alkalinity. Beta-amine (IV), keji-dimethoate and iso-sulphuric acid are generally known and It can be said from the market 20. WO 2006/ Compounds of the general formula (II) can be obtained by a method similar to that known from the literature (for example, 127426). 22 200902505 Scheme 1

The reaction of a suitably substituted benzylamine with a suitably substituted 2-chloroethyl isocyanate (e.g., 1,4-dioxane or dichloromethane), as shown in Scheme 1, yields a suitably 5-substituted 1-benzyl group. -3-(2-chloroethyl)urea, in combination with a base (eg NaOH, H20, 1,4-dihydroalkane or diazo(1,3)bicyclo[5.4.0]undecane (DBU), After heating with acetonitrile, an appropriately substituted 1,3-hydrazine amine (II) is produced. Such methods are generally known to those skilled in the art (WO 2006/127426, pages 22, 26; WO 2005/063724, page 56, and references cited therein). 10 A novel substituted compound of formula (I) wherein R8 is -P(S)RnR14 is a compound of formula (II)

Wherein R1, R2, R3, R4, R5, R6 and R7 are as defined above 23 200902505 and a chlorophosphorothioate of formula (χι) C1-P(S)R13R14 (XI) wherein R13R14 is as defined above and organic or An inorganic base in an aprotic solvent such as dichloromethane, gas, acetonitrile, dimethyl decylamine, tetrahydrofuran or ethyl acetate at a temperature of from -20 to 120 ° C (preferably 0- Obtained at 40 ° C depending on the solvent. The reaction time is from 1 to 20 hours, and the ratio of the precipitates, the compound of the formula II: chlorothiophosphoric acid S: the base is from 1:1:1 to 1:2:5, preferably 1:1.1:3. Preferred bases are amines such as triethylamine, diisopropylethylamine, pyridine, dinonylaminopyridine. 10

0,0-Dialkylchlorothiophosphate (XI) is well known and commercially available (eg, 0,0-dimercaptochlorophosphorothioate [CAS 2524-03-0], 0,0-two Ethyl gas 15 phosphorothioate [CAS 2524-04-1]). A novel substituted compound of formula (I) wherein R8 is -C(0)R1Q or -C(0)OR10 and R12 is hydrogen, as a compound of formula (II) 24 20 200902505

7 NIH

R

R and a compound of the formula (V) XC(0)R10 or XC(O)ORi0(V), wherein R1Q and R11 are as defined above and X is a leaving group such as halogen, or a compound O of the formula (VI) (- C(O)R10)2 (VI) Obtained under alkaline conditions in an aprotic solvent. Such reactions are well known to those skilled in the art (see WO 2006/10 127426, pages 23 and 32). Compounds of formula (VI) are well known and commercially available from the market. Process 2

R

R,

Solvent

25 200902505 In the reaction shown, 'organic and inorganic bases are useful "column U soil fee, money potassium"' is preferably non-quality, preferably between the machine. 5, the last is now novel The compound of formula (1) has remarkable biological characteristics, and is particularly suitable for controlling the regrets encountered in agriculture, forests, storage products, and in the health industry, and the animals are covered, especially Insects, arachnids, and green worms. - "Two types: The upper objects may exist in different homomorphic forms or different from the same '10'. Pure homogeneous homomorphic and homogeneous polymorphic mixtures are provided by the present invention and can be used in accordance with the present invention. - combining the active compounds with good plant tolerance, suitable toxicity to warm gold animals and enduring the active compounds of the invention, which are suitable for the protection of plants and plants: the yield of the sylvestre or the sorghum, improving the quality of the harvested material and Control animal pests, knowing how to be in the industry, horticulture, animal husbandry, forests, flower gardens and leisure equipment, 15 in the protection of stored products and materials, and insects, arachnids, creeps commonly found in the health industry. Insects, nematodes and mollusks. They are preferably used as crop protection agents. They are active against general sensitive and resistant species and for all or part of the development phase. The above pests include: 13⁄4 mesh (Ranunculus), such as the genus Damalini, the genus Haemat0_ 20 pinus, the genus Linognathus, the genus Pediculus, and the Trich-odectes. ) genus. Arachnidae such as Acarus siro, Aceria sheldoni, Aculops, Aculus, Amblyomma, Argas Genus, Boophilus genus, Brevipalpus 26 200902505 Genus, Bryobia praetiosa, Chorioptes genus, Dermanyssus gallinae, Eotetranychus genus, Epitrimerus pyri, Eutetranychus, Eriophyes, Hemitarsonemus, Hyalomma, Ixodes, Black widow, Latrodectus mactans, Metatetranychus, Oligonychus, Ornitho-doros, Panonychus ), Polyphagotarsonemus latus, Psoroptes, Rhipicephalus, Rhizoglyphus, Sarcoptes, Scorpio maurus, Narrow Line (Stenotarso-nemus), line (Tarsonemus), leaf full (Tetran Ychus) genus, tomato thin worm (Vasates lycopersici). Bivalve, such as the genus Dreissena. The lip-footed genus, such as the genus Geophilus and the genus Scutigera. 15 Coleoptera, such as Acanthoscelides obtectus, Adoretus genus, Agelastica alni, Agriotes genus, Amphimallon solstitialis, furniture mites (Anobium) Punctatum), Anoplophora genus, Anthonomus, Anthrenus, Apogonia, 20 Atomaria, Attagenus, soybean Elephant (Bruchidius obtectus), Bean (Bruchus) genus, Ceuthorhynchus genus, Cleonus mendicus, Conoderus genus, Cosmopolites genus, Grassland terrapins (Costelytrazealandica) ), Curculio, Cryptorhynchus lapathi, Dermestes 27 200902505 Genus, Diabrotica, Epilachna, Faustinus cubae, naked Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hyena weevil (Hy Pera 5 postica), Hypothenemus genus, Lachnosterna consanguinea, Leptinotarsa decemlineata 'Lissorhoptrus oryzophilus, Lithus genus, Lyctus Genus, Aquila aereus, Melolontha melolontha, Migdolus genus, Mono-10 chamus genus, Naupactus xanthographus, Yellow spider mites (Naupactus xanthographus) Niptus hololeucus), Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga, Popillia japonica, Premnotrypes, Psylliodes chrysocephala, Ptinus, Ladybug (Rhizobius-i. ventralis) , Rhizopertha dominica, Sitophilus, Sphenophorus, Sternechus, and Sym-phy Letes), Tenebriomolitor, 20 genus of Tribolium, genus Trogoderma, genus Tychius, genus Xylo-trechus, walking distance Zabrus) genus. The bullet tail ‘for example, the insect nematode (Onychiurus armatus). The genus Hymenoptera, such as the Forficula auricularia. The foot of the genus 'Blaniulus guttulatus'. 28 200902505 Diptera, such as Aedes, Anopheles, Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia Spiral fly ((: 〇0]11丨〇11^3) genus, anthropomorphic larvae ((:(^(171〇1^&11〇〇??〇?1^§3), 5 library Culex, genus Cutrebra, Dacus-oleae, Dermatobia hominis, Drosophila genus, Fannia genus, Gastrophilus genus, The genus Hylemyia, Hypoposca, Hypoderma, Liriomyza, Lucilia, Musca, Nezara , Oestrus genus, Oscinella frit, Pegomyia hyoscyami, Phorbia, Stomoxys, Tabanus, Tannia Genus, Tripulapaludosa, and genus Wohlfahrtia. Gastropods such as the genus Arion, the genus Biomphalaria, and the water 15 snail (Bulinus) genus, genus (Deroceras), genus (Galba), genus Lymnaea, genus Oncomelania, genus Succinea. Spirulina, such as duodenal hookworm (Ancylostoma) Duodenale), Ancylostoma ceylanicum, Acylostoma brazi-liensis, Ancylostoma genus, Ascaris lubri-20 coides, Ascaris genus, Malay Brugia malayi, Brugia timori, Bunostomum, Chabertia, Clonorchis, Cooperia, Dicrocoelium, Dictyocaulus filarial, Diphyllobothrium latum, Dracunculus 29 200902505 medinensis, Echinococcus granulosus, Echinococcus multilocularis Enterobius vermin-cularis, Faciola genus, Haemonchus genus, Heterakis genus, short-coated aphid (Hymenole) Pis nana), 5 Hyostrongulus genus, Loa Loa, Nematodirus, Oesophagostomum, Opisthorchis, Onchocerca volvulus, Ostertagia genus, Paragonimus genus, Schistosomen genus, Stron-gyloides fuelleborni, Strongyloides stercoralis, 10 genus Stronyloides, Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella native, Trichinella britovi, Trichinella nelsoni, Trichinella pseudoopsiralis, Trichostrongulus genus, Trichuris trichuria, Wuch-15 ereria bancrofti. It further controls protozoa, such as Eimeria. Heteroptera, such as Anasa tristis, Antestiopsis, Blissus, Calocoris, Cam-pylommalivida, Cavelerius, bedbugs (Cimex) genus, Creontiades dilutus, Dasynus piperis, Diechels furcatus, Diconocoris hewetti, Dysdercus genus, Euschistus genus, Eurygaster, Heliopeltis, Horcias nobilellus, Leptocorisa, Leptoglossus phyllopus, Lygus genus, 椿30 200902505 (Macropes excavatus), blind Miridae, Nezara, Oebalus, Pentomidae, Piesema quadrata, Piezodorus, Pseudos Seriatus), lace bed bug (Pseudacysta persea), rhododendron (Rhodnius), 5 cocoa blind singularis (Shlbergella singularis), Scorpion genus (Scotinophora) genus, and sacred scorpion scorpion (Stephanitis nash) i), the genus Tibraca and the genus Triatoma. Homoptera, such as the genus Acyrthosipon, Aeneolamia, Agonoscena, Aleurodes, Aleurolobus barodensis, Aleurothrixus), Amrasca genus, Anuraphis cardui, Aonidiella genus, Aphanostigma piri, Aphis genus, Arboridia apicalis, small round Aspidiella, Aspidiotus, Atanus, Aulacorthum 15 solani, Bemisia, Brachycaudus heli-chrysii, Brachycolus genus, Brevicoryne brass-icae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cerco-pidae, Ceroplastes, Chaetosiphon fragae-20 folii, Indonesian Chionaspis tegalensis, Chlorita onukii, Chromaphis jugla Ndicola), Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus genus, Cryptomyzus ribis, Dalbulus genus, powder l^(Dialeurodes Genus, Diaphorina genus, genus 31 200902505 genus Diaspis, genus Doralis, Drosicha genus, Dysaphis genus, Dysmicoccus genus, leaf mites Empoasca) genus, Eriosoma genus, Erythroneura genus, Euceleli bilobatus, coffee. Geococcus coffeae, Homalodisca coagulate, Hyalopterus arundinis, Icerya genus, Idiocerus genus, Idyscopus Genus, Laofeiphax striatellus, Lecanium genus, Lepidosaphes genus, Lipaphis erysimi, Macrosiphum genus, Mahanarva fim-brolata ), Melanaphis sacchari, Metcalfiella, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecalis, Myzus, Lettuce (Nasonovia ribisnigri), Nephotettix genus, Nilaparvata lugens, Oncometopia genus, Orthezia 15 praelonga, Parabemisia myricae, 枸杞Paratrioza, Parlatoria, Pemphigus, Peregrinusmaidis, Phenacoccus, and Ploeloeyz Us passerinii), Phoropon humuli, Phylloxera genus, Pinnaspis aspidistrae, 20 genus Planococcus, Protopulvinaria pyriformis, Pseudaulacaspis penta-gona, Pseudococcus, Psylla, Ptero-malus, Pyrilla, Pyraspidiotus ), Quesada gigas, Rastrococcus genus, Rhopalosiphum 32 200902505 genus, Saissetia genus, Scaphoides titanus, Schizaphis graminum, thorn round shield scale (Selenaspidus articulatus), scorpion (Sogata), Sogatella furcifera, Sogatodes genus, Stictocephala festina 'Tenalaphara malayensis, Tinocallis 5 caryaefoliae, Tomispis, Toxoptera Genus, Trialeurodes vaporariorum, Trioza genus, Typhlocyba genus, Unaspis genus, Square grape phylloxera (Viteus vitifolii). Hymenoptera, such as the genus Diprion, the genus Hoplocampa, the genus 10 of the genus Lasius, the genus Monomorium pharaonis, and the genus Vespa. Isopods, such as Armadillidium vulgare, Oniscus asellus, Porcellio scaber, etc., such as the genus Reticulitermes and the genus Odonto-15 termes. Lepidoptera, such as Acronicta major, Aedia leucomelas, Agrotis genus, Alabama moth (Bucculatrix thurberiella), pine scorpion (Bupalus 20 piniarius) ), Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo genus, Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus genus, cotton spotted moth (Eariasin-5111&11&), Mediterranean pink spotted mold (£11681^1) <;1^111^11&), brown-tailed moth (ugly 1*0〇1^33 200902505 chrysorrhoea), genus Euzoa, genus Feltia, auspicious (Galleria) Mellonella), Helicoverpa genus, Heliothis genus, Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma genus, Lithocolletis Blancardella), Lithhophane antennata, Loxagrotis albicosta, Lymantria genus, yellow-brown caterpillar (]^1&1&003011^1^1181;1^), cabbage blue moth (]\^111651^1^338 &;6), Mocis repanda, Mythimna separate, Oria genus, Oulema oryzae, Panolis flammea, Pectino-10 phora gossypiella, citrus Phyllocnistis citrella, Pieris genus, Plutella xylostella, Prodenia genus, Pseudaletia genus, Pseudoplusia inclu dens, Rhododendron (Pyrausta nubilalis), Spodoptera genus, The Rmesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia. Orthoptera, such as Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa, Florida (Leucophaeamaderae), Locusta, and Emperor Melanoplus, Periplaneta Americana, Schistocerca gregaria, 蚤, such as Ceratophyllus, Xenopsylla cheopis ° Symphyla For example, Scutigerella immaculate. Thysanoptera, such as Balithrips biformis, Enneothrips 34 200902505 flavens, Frankliniella, Heliothrips, Hercinothrips femoralis, Kakothrips, Rhipiphorothrips cruentatus, Scirtothrips, Taeniothrips cardamoni, and Thrips. 5 total tail, such as Lepisma saccharina. Plant parasitic nematodes, including, for example, the genus Anguina, the genus Aphelenchoides, the genus Belenoaimus, the genus Bursaphelenchus, the genus Ditylenchus dipsaci, and the genus Globodera , Heliocotylenchus genus, Heterodera genus, Longidorus genus, Meloidogyne genus, Platyllenchus genus, Radopholus similes, Rotylenchus genus, The genus Trichodorus, the genus Tylenchorhynchus, the genus Tylenchulus, the genus Tylenchulus semipenetrans, and the genus Xiphinema. 15 If appropriate, the active compounds according to the invention, at certain concentrations or application rates, can also be used as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example fungicides Agents, antifungal agents, bactericides, viricides (including antiviral agents) or as agents against yjL〇 (Mycoplasma-like organisms) and RLO (rickettsial-like organisms). 20 If appropriate, 4 can also be used as an intermediate for the synthesis of other active compounds. / The active compound can be converted into traditional formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for dispersion Suspension_emulsion concentrate 35 5 10 15 20 200902505 The substance, the natural substance soaked with the active compound, the substance soaked with the active compound, the fertilizer and the microencapsulation in the polymerizable substance. D. These formulations are prepared in a known manner, for example by mixing the active compound and the second agent, which are liquid solvents and/or solid carriers, optionally using surface agents and/or dispersants and/or foams. _Ingredients). The formulation is prepared at a suitable factory or elsewhere during use or during use. ', suitable for use as an adjuvant is suitable for imparting the active compound itself and / / (for example, spray liquid, Seed dressings (Special properties (such as secret and / or special biological impurities) (4). Typical additives are: extenders, solvents and carriers. 7 Rare as St extender such as water, polar and non-polar organic chemistry Liquid, Example 13 Fragrance and non-aromatic hydrocarbons (such as paraffin, p, A ^, chlorobenzene), alcohols and polyols, silk naphthalene / shame, right right Substituted, etherified and/or sulfonated), ketones (such as acetone, cyclohexanone), vinegars and (poly)ethers, unsubstituted and substituted amines '9 bases (4) and (10), brewed; ^ The liquid solvent of dimethyl 1 * field is: aromatic compound, such as gas stupid, gas Γΐϊΐ na; gasified aromatic Compounds and chlorinated aliphatic hydrocarbons, ethers and vinegars of these; _/methods, as far as butanol or ethylene glycol, and cyclohexyl. Strong 炻1 such as acetone, acetophenone, sulfhydryl Isobutyl ketone or = strong polar agent, such as dimethyl sulphur; and water. Suitable solid carrier: 36 200902505 For example, ammonium salts and ground natural minerals such as kaolin, clay, talc, sarcophagus, quartz , magnesium aluminum sepiolite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely dispersed fine vermiculite, bauxite and citrate; suitable solid carriers for granules are: natural pulverized and classified Rocks, such as calcite, marble, pumice, 5 sepiolite and dolomite, as well as synthetic particles of inorganic and organic grain flour, and particles of organic matter such as paper, sawdust, coconut shell, corn cob and tobacco rod; suitable emulsification Agents and/or foam formers are, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkyl aryl poly(ethylene ether ethers), alkyl sulphate salts, bases Sulfate, aryl rhein And protein ίο hydrolysate; suitable dispersions are nonionic and/or ionic substances, such as from alcohol-POE- and/or -POP, acids, acids and/or p〇p_p〇E vinegars, aryl aryl And/or Ρ0Ρ-Ρ0Εethers, lipid-and/or P〇p_p〇E adducts, p〇E_ and/or POP-polyol derivatives, p〇E_ and/or p〇p_sorbose Alcohol vinegar _ or sugar adduct, alkyl or aryl sulphate, phenolic or aryl sulphate and alkyl or 15 s sate or corresponding P 〇--addition. In addition, appropriate Oligomers or polymers such as those derived from ethylene monomer, derived from acrylic acid, derived from EO and/or PO alone or in combination with, for example, (poly)alcohols or (poly)amines. Lignin and its sulfonic acid derivatives, unmodified and modified cellulose, aromatic and/or aliphatic acid and their adducts with meth can be used. 20 tackifiers, such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as acacia, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, And synthetic phospholipids can be used in the formulation. Colorants such as inorganic pigments such as iron oxide, titanium oxide and 37 200902505 Prussian blue 'and organic dyes' such as alizarin dyes, azo dyes and metal phthalocyanine dyes and micronutrients such as iron, may also be used. Manganese, rotten, copper, Ming's molybdenum and zinc salts. Other possible additives are fragrances (mineral or vegetal), selectively modified oils, waxes and nutrients (including micronutrients) such as iron, manganese, boron, copper, indium, molybdenum and zinc salts. Stabilizers, such as low temperature stabilizers, preservatives, antioxidants, light stabilizers, or other agents that improve chemical and/or physical stability may also be present. The formulation typically comprises between 〇.〇1 and 98% by weight of the active compound, preferably between 0.5 and 90%. The active compounds according to the invention can be used in the formulations which are commercially obtainable, and can be one in the form of use prepared from such formulations, such as insecticides, attractants, A mixture of fungicides, bactericidal agents 15, acaricides, nematicides, fungicides, growth-adjusting substances, herbicides, safeners, fertilizers or semi-chemicals. Particularly desirable mixed ingredients are, for example, the following compounds: Fungicides: Benalaxyl, Bendari-M, Bupirimate, Chiralaxyl, Klein (clozylacon), dimethirimol, ethirimol, fural- axyl, hymexazol, metalaxyl, chlorpyrifos-methyl (ofurace), 杀xadixyl, oxolinic acid 38 200902505 Inhibitors of mitosis and cell division, benomyl, carbendazim, di-ethofencarb ), fuberidazole, pency-curon, thiabendazole, thiophanat-5 methyl, oxaxamide respiratory chain complex I inhibitor difluoride Forest (diflumetorim) inhibitor of respiratory chain complex II, boscalid, carboxin, fen-10 furam, flutolanil, fura gram ratio (furametpyr ), mepronil, oxycarboxin, D-bacteria (pen-thiopyrad), thifluzamide inhibitor of respiratory chain complex III, azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, Wherein (famo-xadone), fenamidone, fluoxa-strobin, kresoxim-methyl, metom-inostrobin, lysine (orysastrobin), pyra-clostrobin, picoxystrobin 20 decoupling agent dinocap, fluazinam inhibitor of ATP, fertin acetate (Fentin acetate) ), fentin chloride, fentin hydroxide, silthiofam 39 200902505 Amino acid biosynthesis and inhibitor of egg biosynthesis aniline σ Andoprim, blasticidin-S, cyprodinil, kasugamycin, carnitamicin hydrogen chloride hydrate, mepanipyrim, pyrimethanil Pyri- methanil) 5 information transmission inhibitor fenpiclonil, Flu dixonitrile, quinoxyfen, an inhibitor of fat and membrane synthesis, chlozolinate, iprodione, pro-10 cymidone, vinclozolin , apropylfos, ampicone, edi-fenphos, iprobenfos (IBP), iso-prothiolane, pyrazophos, armor Tolclofos-methyl, biphenyl 15 iodocarb, propamocarb, proppamide hydrogen ergosterol biosynthesis inhibitor fenhexamid , azaconazole, bitertanol, bro-muconazole, cyproconazole, diclobutrazole, difenoconazole, sulphate (dini-conazole), acesulfon-oxime, epoxiconazole, etaconazole, fenbuconazole, flu flu-nconazole, flusilazole, defensive Flutriafol, furconazole, fluconazole-cis, phoenix (hexa- conazole), 40 200902505 imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, Propiconazole, prothioconazole, simeconazole, tebuconazole, tetra-conazole, triadimefon, triadimenol, sterilization Triticonazole, uniconazole, voriconazole, imazalil, chlorhexidine sulfate, oxpoconazole, fenarimol, beta melamine (fhir-primidol) ), nuarimol, pyrifenox, triforine, pefurazoate, pro- chloraz, triflumizole, viniconazole , aldimorph, dodemorph, valerian acetate, fenpropimorph, tridemorph, fenpropidin, spiroxamine Enemy Naftifine), pyributicarb, terbi-nafine cell wall synthesis inhibitor bethiavalicarb, bialaphos, dimethomorph, flumorph ( Flumorph), iprova_ licarb, granulomycin 曱 (p〇ly〇xins) Agents carpropamid, diclocymet, grass herb 41 200902505 (fenoxanil), phthalide, pyroquilon, tricyclazole resistance induced Agent acibenzolar-S-methyl, proben-5 azole, tiadinil multisite (captafol), captanf (captan) , chloro-thalonil, copper salts (such as: copper hydroxide, copper naphthalate, copper oxide, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture 10 (Bordeaux mixture )), dichlofluanid, dithianon, dodine , more fruit, free base, ferbate, folpet, fluoro-folpet, guazatine, gram heat acetate, diimoctylamine, gram heat Net benzene sulfonate, bis-octylamine triacetate, mancopper, mancozeb, maneb, metiram, free of zinc, sulfhydryl Propineb, sulfur, and sulfur preparations containing polysulfide, thiram, tolylfluanid, zineb, ziram unknown mechanism 20 abromo (amibromdol), benthiazol, bethoxazin, capsimycin, car-vone, chinomethionat, chloropicrin, copper Cufraneb), cyflufenamid, cym-oxanil, dazomet, debacarb, chlorpyrifos 42 200902505 (diclomezine), dichlorophen, gram Diclo-ran, difenzoquat, benzoic acid, diphenylamine, 0 sputum (ethaboxam), ferimzone, flumetover, flusulphamide, fluopicolide, fluoroimide, hexachlorobenzene, 8-jing Base sulphate sulphate, irumamycin, metha-sulphocarb, metrafenone, guanidinium isothiocyanate 5, mildiomycin, streptomycin (natamycin) ), nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxy-fenthiin, pentachlorophenol and Salt, 2-phenylphenol and salt, piperalin, propanosine-sodium, propoxysium uranium (pr〇qUinazid), p ratio ρ each succinic acid reagent ( Pyrrolnitrin), quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamid and { 2,3,5,6-tetrachloro- 4-(methylsulfonyl)pyridine, N-(4-chloro-2-nitrophenyl)-ethyl-4-mercaptobenzenesulfonamide, 2-amino-4-indenyl-N -Phenyl-5-thiazolylmethamine, _2-gas-N-(2,3-dione-1,1,3-didecyl-1H-pyrimidin-4-yl)-3-α ratio Amine, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolin-3-yl]0-pyridyl, 20 cis 4-(4-carbo-phenyl)- 2-(1Η-1,2,4-triazol-1-yl)cycloheptanol, 2,4-dihydro-5-methoxy-2-mercaptotrifluoromethyl)phenyl]ethylidene Amino]oxy]indolyl] phenyl]-3Η-1,2,3-triazol-3-one (185336-79-2), methyl 1-(2,3-dihydro-2, 2-dimercapto-111-indol-1-yl)-111-imidazole-5-decanoate, 3,4,5-tris-2,6-pyridinedicarbonitrile, fluorenyl 2-[[[ring Propyl [(4_decyloxy43 200902505-phenyl)imido]indenyl]thio]indolyl>α·(decyloxyindenyl)phenyl acetate, 4-chloro-α- Propynyloxy_N_[2_[3_曱oxy_4_(2-propynyloxy)phenyl]ethyl]phenylethylamine, (2S)_ n_[2[4_[[3_( 4-(Chlorophenyl)-2propynyl]oxy-3-indolylphenyl]ethyl]_3_methyl_2_[(methylsulfonyl)amino]butanamine, 5-chloro-7 -(4-mercaptopiperidinyl)_6_(2,4,6-trifluorophenyl)[1,2,4]-triazolium, 5々]pyrimidine, 5-chloro-6 (2,4 ,6-trifluorophenyl)N [(1 ft)-1,2,2-dimercaptopropyl]_[1,2,4] 〇 基 基 、, 5-H-N-[(1R)-1,2-dimethylpropyl]_6_(2,4,6-trifluorophenyl)[1,2,4]triazolyl [i,5-a]pyrimidine_7-amine 'gas pyridine 2_yl)ethyl]-2,4-dichloronicotinium amide, ^_(5_bromo_3_chloropyridine_2-yl曱]]-2,4-dichloroacetone test guanamine, 2_butoxy _6_ -3-propylbenzopyrano-4 ketone, N-{(Z)-[(cyclopropyl) Methoxy)imino][6-(difluoromethoxy)_2,3-difluorophenyl]methyl}-2-phenylacetamide, N-(3-ethyl-3,5,5- Trimethylcyclohexyl)-3-decylamino-2-hydroxybenzamide, 2[[[[1-[3(1-fluoro-2-phenyl-ethyl)oxy]phenyl] Ethylene]amino]oxy]indolyl]_α_(methoxyimino)-indenyl-indenyl-αΕ-phenethylamine, Ν_gas_5_(trifluoromethyl) σ-pyridin_2_ Ethyl]ethyl}-2-(trifluoromethyl)benzamide, ν-(3,4,-dichloro-5-fluorobiphenyl-2-yl)-3-(monofluoroindolyl) -1-mercapto-lH-α ratio -4-anthracene amine, N-(6-decyloxy-3-pyridyl)cyclopropanecarbamide, b[(4-decyloxyphenoxy) Indenyl]-2,2-monomethylpropyl-1Η-σm β sit-1-carboxylic acid, 〇-[l-[(4-decyloxyphenoxy)indolyl]-2,2-di Mercaptopropyl-111-imidazole-1-thiopurine , 2_(2丨[6_(3_ gas-2-mercaptophenoxy)_5-fluoropyrimidin-4-yl]oxy}phenyl)_2-(methoxyimino)-indole-methyl- Acetamide 44 200902505 Fungicide: bronopol, dichlorophen, nitra-pyrin, nickel dithiocarbamate, kasu-gamycin ), octithrinone, 0 sulphonic acid, oxytetracycline, 5 probenazole, streptomycin, teclo-ftalam, copper sulphate and other copper preparations. Insecticides/Acaricides/Nematicides: Acetone cholinesterase (AChE) inhibitors, amino phthalates, such as alanycarb, aldicarb, aldoxycarb , allyxycarb, aminocarb, bendiocarb, benfuracarb, bu-fencarb, butacarb, butocarboxim, Butanone 15 (butoxycarboxim), carbaryl, carbofuran, carbosulphan, clo-ethocarb, dimetilan, ethiofencarb , fenobucarb, fenthiocarb, formetanate, furathiocarb, isopro-20 carb, metam-sodium ,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, prome- carb, propoxur , thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb Sansuimai 45 200902505 (triazamate) Organophosphates such as acephate, azamethiphos, azinphos (-mercapto'-ethyl), bromophos- Ethyl, Mofen 5 (bromfenvinfos) (-methyl), butathiofos cadusafos, carbophenothion, chlorethoxyfos, flufensone (chl 〇rfenvinphos), chlormephos, chl〇rpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenapyr Chlorfenvinphos, dimeton-S-methyl, dimeton-S-methyl sulphon, dialifos, diazinon, dichlofenthion, Dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulphoton, EPN, acesulfame (ethion), extho-prophos, etrimfos, ammonia (fam) Phur), fenamiphos, fenitrothion, fensu-lfothion, fenthion, flupyrazofos, fonofos, fosson ( Formothion), fosmethilan, fosthiazate, hepteno-phos, iodofenphos, iprob-enfos, isazofos , Isofens (isofenphos), isopropyl 0_salicylate, isoxathion, mara-thion, degassot 46 200902505 (mecarbam), methacrifos, damasson (methamidophos), methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion ) (-methyl/ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb , phoxim, pirimiphos (-mercapto/ethyl), profenofos, Propa- phos, propetamphos, prothiofos, prothoate, pyraclofos, pyri-daphenthion, pyridathion , quinal- phos, sebufos, sulfotep, sulprofos, tebupirimfos, teme_ phos, tofufos ), Le 15 tetrachlorvinphos, thiometon, triazophos, trichon lorfon, vamidothion sodium channel regulator / voltage-dependent sodium channel resistance Pyrethroid acetal vinegar, such as acrinathrin, allethrin (d-cis-trans, 20 d-trans), beta-saiconin, bifenthrin, bio-Asia Bioallethrin, 百亚烈宁-S-cyclopentyl-isomer, bioethanomethrin, bioperme-thrin, bioresmethrin, chloroproline (chlova- porthrin), cis-cyenmethrin, cis-column-Ning, cis-Bai-Ning, chlorofluoro Cyanocystine 47 200902505 clocythrin, CyCi〇pr〇thrin, Sai Fanning, Cyhalothrin, Sai Ningning (α-, β-, θ-, ζ_), match Cyphenothrin, deltamethrin, empenthrin (lR-isomer), esfenvaierate, ethenin 5 (et〇fenProx), fenfluthine ), fenpropathin, fenpy- rithrin, fenvalerate, fiubroCyh- rinate, flucythrinate, flufenfrin (f|ufenprox) ), fiumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, λ - lambda- cyhalothrin, metofluthrin, fentanin (cis-, trans-), phenothrin (1R-trans-isomer), Plein Prallethrin, profluthrin, pr〇tri_ fenbute, pyresmethrin, resmethrin, RU-15525 Silafluofen, taufluva-linate, tefluthrin, terallethrin, tetramethrin (1R isomer), talazine (tralo-) Methrin), transfluthrin, ZXI 8901, pyrethrum

20 DDT Oral oxadiazines, such as indoxacarb, semi-carbazone, such as metaflumizone (BAS3201) 48 200902505 Acetylcholine receptor agonist/antagonist chloronicotinoid For example, acetamiprid, dothianidin, dinotefuran, imidacloprid, niten-5 Pyram, nithiazine, syke ( Thiacloprid), imidaclothiz, AKD-1022, thiamethoxam nicotine, bensultap, cartap, acetylcholine receptor modulator, spinosyns 10, for example, spinosad, spinetoram (XDE-175) GABA-controlled chloride channel antagonist organochlorines, such as camphechlor, chlordane, Endosulphan, γ-HCH, HCH, heptachlor, lindane, methoxychlor, fiprols, such as acetoprole, loved land White (ethiprole), fipronil, pyrafluprole , pyripole, vaniliprole 20 chloride channel activator mectins such as abamectin, emamectin, b. butyl benzoate , ivermectin, lepi- mectin, milbemycin 49 200902505 Juvenile hormone mimics such as diofenolan, ep0fen〇nane, Fenoxycarb, hydroprene, kinop-rene, metoprene, pyripr0Xyfen, triprene, peeling copper activator / destructive diterpenoids such as chromafenozide, hafenofozide methoxyfenozide, tebufenozide 10 chitinogenic synthesis inhibitor benzammonium, such as double three Bistrifluron, chlorfluaz- uron, diflubenzuron, fhiazuron, flucycloxuron, flufenoxuron, hex-15 Aflunmron), lufenuron, bisphenol fluoride (noval-uron), promise隆iflumuron, penfluron, teflubenzuron, triflumuron, buprofezin, cyromazine 20 oxidative phosphorylation inhibitor, ATP breaker Diafenthiuron organotin compounds, such as azocyclotin, cyhexatin, fenbutatin-oxide 50 200902505 oxidative squaring decoupling σ ratio by interference Η-proton gradient 11 types, such as chlorfenapyr dinitrophenols, 5 such as bina (acryl), din〇but〇n, white powder

(dinocap), DNOC address-I electron transport inhibitor METI's classes such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, pyridoxamine Tebu- fenpyrad), tolfenpyrad hydramethylnone dicofol address-II electron transport inhibitor 15 rotenone address-III electron transport inhibitor acequinocyl Fluacrypyrim Insect gut membrane microbial disruptor Surino strain 20 Fat synthesis inhibitor telronic acid, such as spirodiclofen, spiromesifen, tetramic acid Acids), for example spirotetramat 51 200902505 Amidamines such as flonicamid octopamine production activators such as amitraz 5 magnesium-irritant ATPase inhibitors, Oukou Farargite (neragetoxin) analogues such as thiocyclam hydrogen oxalate, thiosultap-sodium 10 ryanodine receptor antagonist benzoic acid II Indoleamines such as flubendiamide anthranilamides, such as rynaxypyr (3-bromo-N-{4-chloro-2-methyl-6-[(decylamine 15 yl) )carbonyl]phenyl}-1-(3-chloropyridin-2-yl)-1Η-pyrazole-5-decylamine) biological hormone or pheromones' azadirachtin, Bacillus subtilis, 20 active compounds such as Beauveria, codlemone, genus, genus, genus, and genus, and 12 active or non-specific mechanisms of action, such as morphogenesis Ilu, mercapto bromide, sulfuric acid fluoride antifeedant, such as cryolite, flonicamid, σ bottom deficiency 52 200902505 (pymetrozine) medium growth inhibitor, such as clofentezine (clofentezine), Etoxazole, hexythiazox 5 amidoflumet, benclothiaz, benzoximate, bifenazate, bromo-propylate ), buprofezin, chinome-thionat, chlordimeform, chloroben-zilate, chloropicrin, ring race Ping (clothiazoben), cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentri- fanil, flubenzimine , flufenerim, flutenzin, gossyplure, hydramethylnone, japonilure, meto-15 xadiazone, petroleum, Sunflower butyl oxide, potassium oleate, pyridalyl, sulfluramid, tetra-difon, tetrasul, triarathene, mabutin It is also feasible to improve a plant's properties with a mixture of other known active compounds, such as herbicides, fertilizers, growth regulators, safeners, semi-chemicals or other agents. The active compounds according to the invention, when used as insecticides, may additionally be present in their commercially available formulations and in the dosage forms prepared from such formulations, as a mixture with synergists . The synergist is a compound which can increase the activity of the active substance, and the added synergist itself is not necessarily used when the active compound according to the present invention is used as an insecticide. Commercially available Nass and Hearts _ Hexue exists as a commercially available blend of a history of inhibitors that reduce the decomposition of active compounds after use in a planting environment. The dosage form used for the preparation of the substance = not. The content of the substance can vary within a wide range of limits. The active human compound of the dosage form is between 0.00000001 and 95 γ 'length between 0.00001 and 1% by weight based on the weight of the active compound. 0 介于 is better than the compound in a conventional manner suitable for the dosage form. All plants and plant parts may be referred to herein as all plants and plant groups according to the present invention, and secondly, planting wild plants or crop plants (including naturally occurring crop plants and 2 can be used for the cultivation and optimization of traditional plants). Plants and genetic engineering obtained by combination of plant methods or combinations of such methods = plants that can or cannot be protected by the rights of plant breeders: planted plants and plant parts mean the above-ground and ground species of all plants. Flowers, examples of which can be mentioned are leaves, needles 2::: such as seedlings; fruits, fruits, seeds, roots, blocks of poor fruits and asexual and sexual reproduction (4), examples = plant parts also include Harvesting tillers and seeds. (4) For example, seedlings, tubers, underground stems, plants and plant parts according to the present invention, according to conventional treatment methods, such as Hn, f & the root brush application, injection, and "hair, atomization" In the case of spreading, coating, and seeding, it is also possible to directly or by means of the compound acting on the environment, and the mixture according to the invention is particularly suitable for treating seeds. Here, 5 10 15 preferably or particularly preferably the composition of the present invention may be mentioned as being preferred. Therefore, part of the damage caused to the crop plant caused by the pest is early from the time of storage = attack day & After the seeds are planted in the soil, during the germination period of the plant: 2. Immediately occurs. This stage is particularly important because the roots of the plant and the damage to the sheath of the plant can cause the whole plant to grow. It is especially important to use suitable composition to protect seeds and germinating plants. It has long been known to treat plant seeds to control pests, and is 2 = good theme. 'However, the treatment of seeds is usually not satisfactory' Solve the series problem. Therefore, it is desirable to develop a method for protecting seeds and germs' which can eliminate additional application after sowing or after the start of the plant stomach. More desirably, the activity used in this way Compound = Appropriate in use to provide maximum protection of the seed and germinating plants from pest infestation without harming the plant itself by the active compound used. In particular, seed = The method also considers the inner silkworm (4) to kill insects, so as to protect the shaft seeds and hair materials under the minimum use of the crops. 20 This 'special wealth of the invention relates to i protect seeds and hair # plants from pests and insects The method of treating the seed by the active compound according to the invention, the invention likewise relates to the use of the active compound according to the invention for the treatment of seeds, in order to protect the seed and the formed plant from pests. Furthermore, the invention It is a seed which has been treated by the active compound according to the invention to obtain protection from ▲ Bao. 55 200902505 The advantage lies in the special system according to the composition of the invention, the treatment of these active compounds not only protects the seed itself, but also protects The plants formed after the teeth are protected from insect pests. In this way, it is possible to dispense with the immediate treatment of the crops at or shortly after sowing. 5 10 15 Furthermore, it must be considered that it is advantageous for the active compound according to the invention to be used for the basal seed, whereby the plants formed by the seed can express the self-quality of the eggs. Fine (d) This is a daily active compounding reduction of these species f. Some pests can be controlled only by the performance of, for example, insecticidal eggs, and are also protected from damage by the active compounds according to the invention. The active compounds according to the invention are suitable for protection; r are the seeds of the above-mentioned plant varieties used in agriculture,/warming, forest or horticulture. In particular, this is, for example, j, metaplasia, rapeseed, canola, sweet millet, soybean, cotton, sugar fungus (eg, beet and feed, sweet leeks), rice, sorghum and millet, wheat, barley, oatmeal, ... Seeds of sunflower, tobacco, horse yam or vegetables (eg tomatoes, cabbage plants). The active compounds according to the invention are likewise suitable for the treatment of watery and vegetable seed forms. The handling of seeds of corn, soybeans, jobs, wheat and two or canola is particularly important. It is also of particular importance to treat gene-transferred seeds with the active compounds according to the invention as mentioned before. This is, for example, a plant seed, which typically comprises at least one heterologous gene that is capable of producing a polypeptide having particular insecticidal properties. In this context, a heterologous gene in a gene-transferred seed can be derived from a microorganism, such as Bacillus subtilis, nodule, 'Tianca, Pseudomonas, Agrobacterium, Trichoderma, Corynebacterium, Mycorrhizal or genus Penicillium. The present invention is particularly suitable for the treatment of genetically modified seeds comprising at least one heterologous gene derived from Bacillus subtilis and whose gene product exhibits resistance to resistance to European jade 56 200902505 Mie** and/or corn rootworm. Particularly preferred are heterologous genes derived from S. cerevisiae. In the context of the present invention, the active compounds according to the invention may be applied to the seed either alone or in a suitable formulation. Preferably, the seed is treated in a condition sufficient to avoid the erroneous condition during the treatment 5. Usually, seeds can be disposed of at any point of the day between harvesting and sowing. The seeds generally used have been isolated from plants and have no flesh, cobs, stems, seed coats, hair or fruit flesh. When treating seeds, it is generally necessary to note that the amount of active compound and/or other added amounts of the active compound applied to the seed is selected such that the germination of the seed 10 is not adversely affected or the formed plants are not damaged. By. This is particularly important in the case of active compounds having phytotoxic effects at certain application rates. As mentioned above, all plants and parts thereof can be treated in accordance with the present invention. In a preferred embodiment, wild plant species and plant varieties, 15 or those obtained by conventional biological breeding methods (such as hybridization or protoplast fusion) are obtained. In another preferred embodiment, the genetically modified plants and plant varieties (genetically modified organisms) obtained by the combination of the conventional methods and the parts thereof are processed by the genetic engineering s'. The terms "part" or "part of plant" or "plant part" have been described above. 20 Particularly good plants which are respectively available from the mall or in the plant variety in use can be treated in accordance with the invention. It should be understood that plant variety has been planted by traditional planting, by mutation or by recombinant DNA technology with novel characteristics ("features"). They may be variants, biotypes and genotypes. Depending on the plant species or plant species, their geographical area and the growing environment (soil, 57 200902505 climate, growing season, nutrition), the treatment according to the invention may also result in superadditive (co-multiplicative) effects. Thus, for example, the application rate and/or the range of action is reduced and/or the activity of the active compounds and compositions used according to the invention is increased, better plant growth, increased tolerance to high or low temperatures, increased Tolerance to drought or water content or soil salt content, increased flowering behavior, easier harvesting, accelerated ripening, higher yield, higher yield of shellfish and/or higher nutritional value Better storage stability and/or processability of the harvested product may exceed the expected effect. Ίο 15

Preferably, the genetically transformed plant or plant variety (obtained by genetic engineering) treated according to the present invention includes all plants which have been genetically modified to receive genetic material which confers such beneficial effects on the rabbits. . Examples of such characteristics ^ better plant growth, increased tolerance to high or low temperature J or water or soil salt content, increased flowering. Force II The heat generation rate, the higher yield, the higher quality and/or the harvested product. More storage stability of the product and/or processing of biological hazards (such as resistance to the disease: plant resistance to animals and micro or viral) strong pathogenic mold, bacteria and / / resistance And increase the plant's special active herbicidal active compounds' such as mites (wheat, 财 [Wang 帛t's example for important crops tomato, said Qifen * ^ not) jade, soybean, horse yam, beet, (fruit Such as apple, half mm Yuzhuo oil and fruit plant soybeans, Ma Yuqi, said 2 orange fruit, feed) 'Special emphasis on corn, in the booty! ^ Road cotton, tobacco and oil & seed. The special emphasis is on the nature of the toxins formed in the complex object (especially the genetic material 58 200902505, such as the genes CrylA (a), Cryl A (b), Cryl A (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, and combinations thereof, which are grown in plants (hereinafter referred to as "Bt plants"), which are plant resistant to insects, arachnids, nematodes And the defensive and snail's defense 5 forces. Special emphasis is placed on increasing plant-induced disease resistance (SAR), systemin, plant antibiotics, evoked factors, and resistance genes, as well as proteins and toxins derived from plants that are resistant to mold, bacteria, and viruses. The defense. Other characteristics that are particularly emphasized are the increased tolerance of plants to certain active herbicidal active compounds such as imidazolium, sulfonium sulfonium, ketones or phosphinotricin (eg "PAT" genes). The genes of the desired characteristics can also be combined with each other in the genetically transformed plants. Examples of "Bt plants" which may be mentioned are corn varieties, cotton varieties, soybean varieties and potato varieties. They are sold under the trade name YIELD. GARD® (eg corn, cotton, soybeans), KnockOut® (eg corn), StarLink® (eg 15 maize), Bollgard® (eg cotton), Nucotn® (cotton) and NewLeaf® (potato). Weeding can be mentioned Examples of agent-tolerant plants are corn varieties, cotton-like ασ species, and large five varieties 'People's traded under the trade name R〇un (JUp Rea (jy® (tolerant Linji, such as corn, cotton) , Soy), Liberty Link® (tolerant to grass, such as rapeseed), IMI® (tolerance to imidazolium), and STS® (tolerant to 20 sulfonylureas, such as corn). Herbicide tolerant Plant (tolerant to herbicides) Examples of plants which are grown in a conventional manner include those sold under the trade name clearfield <S) (for example, corn). Of course, such statements also apply to genetic traits having such genetic traits or developed in the future. A plant variety which will be developed and/or sold in the future. 59 200902505 The plant according to the invention can be treated in a particularly advantageous manner, i.e. by the active compound of the formula I according to the invention. The above preferred ranges of active compounds are also suitable for the treatment of such plants. It is particularly emphasized that the plants are treated with the active compounds specifically mentioned herein. 5 The active compounds according to the invention are not only resistant to plants, hygiene and storage products. Pests can also be used in the veterinary drug industry to combat animal parasites (extra- and intra-parasites) such as hard palate, soft palate, beast, leafhopper, fly (bite and cockroach), parasitic fly larvae, head lice, Feathers and fleas. These parasites include: Insects such as Haematopinus, Linognathus, and Pediculus , genus (Phtirus), tuber (Solenopotes) genus. Phyllostachys and genus and genus, such as Trimenopon genus, genus Menopon, geese (Trinoton) ) genus, Bovicola, Werneckiella, Lepikentron, Damalina, Trichodectes, Felicola. 15 Diptera and Nematocerina and Brachycerina, for example, Aedes, Anopheles, Culex, Simulium, true Eusimulium, Phlebotomus, Lutzomyia, Culicoides, Chrysops, Hybomitra, Atylotus, it 20 (Tabanus) genus, Heittopae genus, Philipomyia genus, Braula genus, Musca genus, Hydrotaea genus, Stomoxys genus, Haematobia Genus, Morellia, Fannia, Glossina, Calliphora, Lucilia, Chrysomyia, Wohlfahrtia Genus, meat rope 60 200902505 (8&1^0卩1^8&) genus, Niu Ji (〇631; 1*113) genus, leather problem (11丫卩0 (161*111&) genus, stomach genus (Gasterophilus) genus, Hippotosca genus, Lipoptena genus, and Melophagus genus. Eyes, such as genus (Pulex), genus Ctenocephalides, genus 5 蚤(Xenopsylla) genus, genus Ceratophyllus. Heteropterida, such as the genus Cimex, Triatoma, Rhodnius, Panstrongylus From the order of the eye, for example, Blatta orientalis, Periplaneta americana, Blattella germanica, Supella genus. Acarina and post-and-middle Meta- and Meso-stigmata, such as the genus Argas, the genus Ornithodorus, the genus Otobius, the genus Ixodes, the flower bud (Amblyomma) ), 15 genus Boophilus, Dermacentor, Jemo phy (Haemo-physalis), Hyaloma genus, Rhipicephalus genus, Dermanyssus genus , the genus Raillietia, the genus Pneumonyssus, the genus Sternostoma, and the genus Varroa. Spodoptera (former valve suborder) and powder worm (no valve suborder), such as the genus Acarapis, the genus Cheyletiella, the genus Ornithocheyletia, the genus Myobia, Psorergates Genus, Demodex genus, Trimbula genus, Listrophorus, Acarus genus, Tyrophagus genus, Caloglyphus genus, Hypodectes genus, Pterolichus, Psoroptes, Chorioptes 61 200902505 • Aphids (Noto-'s larvae (Lami-genus, genus Otodectes, argus (Sarcoptes) edres) ) genus, KnemidoCOptes, Cytodites nosioptes). The compound is also suitable for controlling parasitic agricultural production (such as cattle, sheep, goats, horses, pigs, donkeys, _, buffalo, mutans, chickens, turkeys, ducks, cranes and bees), other pets ( Such as dogs, tracing, cage birds and aquarium fish, as well as arthropods on so-called test animals (such as warehousing, rats and mice). By controlling these sections: easy to die and productivity (for meat, milk, hair, skin, eggs, honey =, can reduce the loss of the valley 10 Ό skin - K 隹, etc.), so that the active compound according to the present invention can have more Economical and more animal husbandry. The active compounds according to the invention are used in the veterinary industry and in the animal husbandry industry in a conventional manner, for example, in the form of tablets, capsules, beverages, veterinary syrups, granules, pastes, daiwan music, penetration methods and drug-drugs. The suppository form 15 is used, for example, by injection (intramuscular, subcutaneous, intravenous, ventral membranous = pre); transplantation, nasal administration, by, for example, soaking or bathing, sneezing, pouring, rubbing, washing, And rubbing powder and application by means of a skin comprising a molded composition of active ingredients such as collars, ear tags, tail tags, limb end bands, reins, marking devices, and the like. When used in livestock, poultry, pets, etc., the active compound of the formula (1) may be in the form of a formulation of the active compound (for example, a powder, an emulsion, a free-flowing composition) of from 203 to 80% by weight, directly or at 100 to They are used after 10,000-fold dilution, or they can be used as chemical baths. It has further been found that the compounds according to the invention also have a strong insecticidal activity against insects which destroy industrial substances. 62 200902505 The following insects can be mentioned as examples and are preferred (but not limited to): bees, such as North American Tenjin (1^1〇1:1*叩68匕3 know1115), 〇11〇 1'〇011〇1^ pilosis, furniture beetle (into 11〇1^11111卩1111(^1:11111), \631:〇1^11111〇1[(^11〇-sum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon Aequale, Minthes rugicollis, Xyleborus genus, Tryptoden-dron genus, Apate monachus, Bostrychus capucins, 10 Heterobostrychus brunneus, double spines (Sinoxylon) genus, Dinoderus minutus; Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, tree bee ( Urocerus augur); 15 termites, such as Europe Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santo-nensis, Reticulitermes lucifugus, Mastotennes darwiniensis , South American termites (Zotermopsis nevadensis), domestic termites 20 (Coptotermes formosanus); Bristletails (Brisletails), such as Lepisma saccharina. The industrial substances described herein should be understood to mean non-living substances, such as (preferably) Plastics, adhesives, coatings, paper and board, leather, wool and processed wool products and coating compositions. 63 200902505 A suitable composition may additionally comprise an insecticide and, if appropriate, one or more fungicides. With regard to other possible additives, the above-mentioned insecticides and fungicides can be mentioned. 5 The compounds according to the invention are likewise useful for protecting objects (especially shells, screens, nets, buildings, moorings and systems) in contact with salt water or brackish water from fouling. Further, the compound according to the present invention, alone or in combination with other active compounds, can be used as an antifouling agent. 10 In the protection of household, sanitary and stored goods, the active compounds are also suitable for controlling animal pests, especially insects and arachnids in confined spaces (eg residential, factory corridors, office to, car trunks, etc.) tick. They may also be used in household insecticidal products alone or in combination with other active compounds and adjuvants to control such pests. They are sensitive to and resistant to species and active for all stages of growth. These pests include: Gossips such as Buthus occitanus. The order of the genus 'Argas persicus, Argas reflexus, Bryobia, Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, 20 enterprises Rhipicephalus sanguineus, Trombula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae °, such as Arvideidae, Araneidae 64 200902505 is a genus. Blind spiders, such as Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, and Opileons phalanxgium. Isopods, such as Oniscus asellus, Porcellio scaber. 5 times the foot of the eye, such as the genus Blanciulus guttulatus, the genus Polydesmus. Lips and feet, such as the genus Geophilus. The suborder of the squid, such as the genus Ctenolepisma, Lepisma saccharina, Lepismodes inquilinus ° 10 蜚蠊, for example, Blatta orientalis, Blattella germanica , Blattella asahinai, Leucophaea maderae, Panchlora genus, Parcoblatta genus, Periplaneta australlasiae, Periplaneta Americana, plucking 蜚Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa. Jumping suborders, such as Acheta domesticus. The genus Hymenoptera, such as the Forficula auricularia. Isoptera, such as the genus Kalotermes and the genus Reticuli-termes. 20 Phytophthora, such as the genus Lepinatus, the genus Liposcelis. Coleoptera, such as the genus Anthrenus, the genus Attagenus, the genus Dermestes, the Latheticus oryzae, the genus Necrobia, the genus Ptinus, the valley Rhizopertha dominica, Sitophilus granaries, Sitophilus oryzae, corn elephant 65 200902505 (Sitophilus zeamais), scorpion locust (Stegobium paniceum). Diptera's such as Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles, Blowfly (匸&1冲11€^ 671;111*006卩11313),〇1730201^口11^也118,热5, Culex quinquefasciatus, Culex pipiens, Culextarsalis, Drosophila , Fanniacani-cularis, Muscadomestica, Phlebotomus, Sarcophagacamaria, Simulium, Stomoxys, Stomoxys calcitrans, Muddy mosquito (Tipulapaludosa). 10 Lepidoptera, such as Achroia grisella, Galleria mellonella, Plodia intei^punctella, Tinea cloacella, Tinea pellionella, and belted clothes moths ( Tineola bisselliella). Hymenoptera, such as enocephalides canis, enocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis. 'Hymenoptera, such as Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula genus, 20 paving Ant (Tetramorium caespitum). For example, Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus genus, Phylloera vastatrix, and Phithrus pubis. Heteroptera, such as the tropical bed bug (Cimex hemipterus), the warm bed bug 66 200902505 (Cimex lectularius), Rhodius prolixus, Triatoma infestans ° In terms of household insecticides, the active compounds according to the invention may be used alone or In combination with other suitable active compounds, such as phosates, amino phthalates, pyrethroids, new nicotines, growth regulators or active compounds from other known classes of insecticides Use it. The active compounds according to the invention can be used in aerosols, pressureless spray products, such as cartridges and micronized sprays, automatic sprays, foams, gels, from cellulose or polymers. Evaporative tablet evaporator product, liquid evaporation 10, gel and membrane evaporator, propellant-driven evaporator, energy-free or passive evaporation system, locust paper and locust rubber, used in the form of granules or powder Spread the bait or use it for feeding. [Examples] 15 Preparation Example: (2Z)-2-{[(lS)-l-(2-fluorophenyl)ethyl Iimino}-N-methyl-1,3-oxazolidine -3-" thioguanamine

Compound (3) 67 200902505 First, 260 mg (1.25 mM Moore) of S-H2-phenylethyl) 13 rosin-2-ylamine was charged to 10 ml of 91*g (1.25 mmol) ) a dichloro T-burn of methyl isothionate, followed by dropwise addition of 150 g (ι, ΐ 6 mmol) ν, Ν-diisopropyl dissolved in soaring dichloropurine Ethylamine. At 2 〇. When the reaction mixture was stirred under stirring for 15 Torr, all the volatile components were finally evaporated and the obtained product was purified by column chromatography on dioxin. Obtained mg (66% of the value of the compound) of compound 3 (l〇g ρ acid 3 18,1H NMR (CDCl3 5.08 ppm)

The scheme can be similarly applied to the compound of the formula (1) wherein R8 is -C(S)N R R and R12 is hydrogen. 15 〇,〇-dimethyl [(2Z)-2-{[(lS)_l-yl] phosphorothioate phenylethyl]imino}-1,3-oxazolidine-3-

Compound (37) 68 200902505 3 〇 0 mg (1.58 Torr) of stupidylethyl] 4,5_di=sal-2-amine and 713 mg (5.52 mmol) of diisopropylethylamine Dissolved in the 2nd gram of the addition of 5 parts of the mixture should be dissolved in 1 ml of di-methane, 24, ') the second base "Sister M. . . The next counter-purification is purified by column chromatography using '1' of all volatile components and the obtained V value of the product. Obtained a combination of milligrams U 0 dV3%) 4"7 (1...Please1·4, brain MR (DMS〇-d6) q 4 66 ppm) 10

Test, solvent CI-P(S)(〇ivie)2 ___

Other compounds of formula (I) are listed in table i below. 69 200902505

荽Φ^(Ι)< :14 _toπ £ r _®-= : was forged (3) (to, latent) dboOI^-recap 9α ossa^(ν,Ιυαυ衾toeNNffi: fin base!ϊ#.Ί^ ν αή Capture physical data 4.78 q (A) 4.74 q(B) 5.08 q (A) 4.76 q(B) 4.78 q (A) ΘΟ P5 C(S)-NH-Me C(S)-NH-Et C (S)-NH-Me C(S)-NH-Et C(S)-NH-Me C(S)-NH-Et ο CD (D (US (U U Ρ fί ffi XKKK 0S XXXX Ρϋ X ffi XK <s (3⁄4 X ffi X P-ι X ffi [Xi pH κ k <0 CN m inch 200902505 physical data 5.85 s (B) 00 Ρϋ C(S)-NH-Me C(S)- NH-Et C(S)-NH-Me C(S)-NH-Et C(S)-NH-Me C(S)-NH-Et C(S)-NH-Me C(S)-NH- Et C(S)-NH-Me C(S)-NH-Et C(S)-NH-Me i C(S)-NH-Et C(S)-NH-Me ww cu s 〇OJ s < υ swmumuoo Ό sm PS ffi K ffi a X ffi XKX Tt K ffi ffi ffi ffi κ K ffi KK ψ "HX ffi ffi ffi KXKXXX κ 1 < ffi ffi ffi X 1 <i"MTMi A Ph b 1 < a X — Pi XXI 4 XKX w ffi X ^ 51 oo Os 〇r—H (N m inch yn oo a\ 200902505 toil ΛλΑ. w 禅龚碱00 P5 w 1 1 /-~N 00 u (ϋ 1 ^: 1 00 um 1 ffi 2; 1 /—v in u <D 1 ffi 1 /-~N GO u ω 1 X z 1 V 00 u (USI ffi 1 00 ow 1 ffi 1 / —V 00 u (U s 1 I /—N 00 uw 1 1 r—N 00 Ό (U s I 1 00 uw 1 z 1 /-—V 00 u V s 1 t /-—v 00 u ω 1 KI /—Ν 00 u <D 1 1 00 u ω 1 ffi 1 00 u mandatory ί <UV 2 V <υ V s V s tu S d> s (DS CD S (DS CD SDS < DD in KK k K ffi K ffi ffi X ffi ffi ffi K τΤ 0ί r "H ffi XX ffi KKK ffi QJ o (US o ffi K ffi ffi fn oi i 1 CD O <L) S 〇 (U o (DS 〇E a (U 2 (D 1 ^ rs PH K Ph iX< EKV so (U o X ffi EKXX a ffi (U s <U s <D o (US 〇<D CD S i H Gong Lai Φ (N (N m <N tn (N (N 〇〇(N 〇\ (N (N CO mm 200902505)

w alkaloid 4.66 q (B) 1.58 (C) 00 pH <D 1 Z 1 /—N 00 u ω 1 K 1 00 u CN "αΤ O y—'-N in Oh (N o 00 Oh CN "oT o 00 Ph <N 〇OO pL( (N <uo 00 <N /•"NW o /—N 00 CLh <NN <D or-s 00 pH CM o /-~N 00 Ph (S r - N < U o 00 s - ✓ (N Ο / - * Ν 00 Ph (NS o 00 £ o 00 CU (N / - NVS o / - N 00 ^ 0 / Ph < 〇Ρϋ (ϋ V <U tu SV s <〇s (U s ω w (D s DS CD S cu ω if) Ρί K ffi K ffi KK ffi ffi X ffi KXK ffi ffi X ffi ffi ffi ffi K r*5 (3⁄4 XXKK ffi K ffi ffi ffi fS PH m [X( u ro IL, u X κ ffi Ph ffi ffi ffi >··Ή ,| H [Jh κ K kk [X* m ffi , 丨一r * w Ffi k review ir> m \〇m P; oo mmor H m Ό OO 200902505 wmagong 00 αί <N £ Ο /—N 00 CN 〇/<--s 00 vw/ Ph (N 〇oo fN V o N in <N o /^N 00 C1h ΓΝί N (US o /*—N 00 Ph CN o 00 Oh (N /—NV 〇/—N 00 Ph <N 〇/—N 00 a. (N /--s V so /^v 00 '>«✓ PL( fN o /— 00 ¢^ <N /— (D o /*·--s 00 Ph CN 〇/--s υο ^—✓ dn Ρϋ ω m Ph υ r〇Ph u O 0 o μ (US 2 CD s (UDS (U cu 艺 ij Ρί ffi K ffi ffi ffi ffi XK ffi KK rr Ρύ ffi κ K ffi i 4 1 < ffi ffi w ffi f^l OS K a K I1"< 1 1 "< ( US o VS o (D o cu o ffi X ts ρμ XX PL< Ph K ffi (U o <υ % 〇Pi KK a X t " H ψ H ffi ffi ffi ffi *<〇<N m ^ T) 5; iT) 〇〇in \〇(N Ό 200902505 tell i&B^kw 禅赛碱00 (N /**—N 0) 〇N 00 Oh (N 〇00 'w^ Ph (N s &lt ;D 〇/^N 00 Ph (N o /-TMN 00 cu ω 〇(U o 〇〇CLh (N 2 〇00 Ph o V o 00 pH <N /^S <uo C>0 y^ / PH fN /*—N (U o /^\ 00 CS £ o in C1h 0> ouwousoumou <uou D 0> CD tu V (UV <u 0> (D CD CU CD <DV αί s S sss SSS ΙΛ (3⁄4 K ffi ffi K ffi XKKKX inch <υ ο (DS o K ffi K ffi ffi ak ffi K m K 0> V s 1"' <^―< ffi KKKKE fS 13⁄4 κ X w ffi amu ΓΛ (Jh u K ffi X Pl — Pi (U (U 1) so <D s 〇<v 2 s 1 1—( ffi ffi XX 赛 m ^r) Ό Ό Ό oo 〇ii (N m inch r- 200902505 荽 base 90 Oi wou 0> 〇omou (US ou ω ou &D; D 〇owou <D ouw 〇u (D 〇u ω 〇u (U souw 8 v〇 (U sw ω a> s <υ s cu s <U ω ω ΓΛ ur〇(X| uo ΰ IT) pi ffi ffi a κ KXKKKKX ffi oi ffi ffi e κ XK ffi ffi a XK fTi m ffi am XXK ffi EX ffi Rs (3⁄4 [X( w ffi X a 1—H I"·1 H pu. b (3⁄4 m KKX ffi ,丨丨丨H 1 < ffi K a EX ffi XX 荽娓〇〇s <N oc r 〇oc tn oc Ό OC oo oo 〇\ oo 200902505

Physical data (D ω < D m < D m (U w D ω (〇W CD SW iU 00 ο ί ou ο ou ou 〇uooou O u 〇u 〇uou 〇uou O u 〇u 〇u V CU < D <U <D <〇(UVVD <D tU CD <D o SS ss SSS s IT) Ρί ffi ffi X ffi ffi X ffi K ffi ffi Pi 1 ti "'·Η ffi K ffi ffi Ffi E ffi a OMe OMe ffi X ffi PH 1 t - - OMe OMe OMe OMe KXXXX <u (〇2 1 < n Pi XX PH Ph ! OMe OMe KXK ffi m — I 1 111 < k KKXE <υ 0) Art OMe OMe 0> s (U i 1 Celluloid Jj ^ T- -3⁄4 (N On m Os σ\ σ\ 〇〇0's 〇\ 〇\ oor··1^ 〇Γν| o r.丨H mor —H inch o H oi—H 200902505

Physical data 00 COEt 1_ COMe COEt COOMe COOEt COOMe COOEt 1 COOMe COOEt COOMe COOEe COOMe COOEt COOMe COOEt (3⁄4 (U s CD S s V cu s S <υ 0>a; sw ω CD CD D <υ 13⁄4 KK ffi KKX κ KK ffi ffi ffi κ Ά KEKX κ XE ffi ffi e Ρί i 1 KKXEX κ XK ffi X <s K r〇U m Ph u K ffi ffi [X. Ptn ffi X ffi ffi i 1 iH i 1 XKXXKKK ffi 1 * ffi X ^ 51 o r- o oo ooo 1—^ i—H t—H ” H (N r—H r_H m inch f 1 H 1 i *r^ i11 H '1 * Ό t—H ”&quot ; H 卜 · · "4 ψ · 1 < OO , _ H i - H Os t < 4 r - H 〇 (N r - H 200902505 physical data 00 COOMe COOEt COOMe . COOEt COOMe COOEe COOMe COOEt COOMe COOEt COOMe COOEt COOMe ω w ΓΛ [Xl um iXi uoo <υ s <DSV (DS (DD s ΙΛ ffi K ffi κ XK ffi ffi Tf K mm K i H i—H ffi ffi K ffi ffi κ K r—^ OMe OMe OMe OMe Μ pH Ph w ffi ffi OMe 1 Pi X k K a XF·( KW ffi ffi ¥铼i-H (N (N (N ψ -H m (N , _ 1 H inch < N ψ "H m (N (N 1 4 r- < N 1 -H oo (N w t ON <N o m r -H r -H m >" 4 <N m t 1H m m i i 200902505

Physical data 5.82 s (B) 00 COOEt COOMe COOEt COOMe COOEt COOMe i COOEt COOMe COOEt COOMe COOEt C(S)-NH-Me C(S)-NH-Me C(S)-NH-Me C(S)-NH -Me V s (U s (UDS cu S (DSD) (DSD = 1), DS 4=1 chf2 chf2 CH2F ΙΛ Οί K ffi ffi ffi K ffi XK ffi ffi ffi ffi Tf Ρύ a ffi OMe OMe ffi a K ffi KXK (3⁄4 XX ffi <DS (D 2 r HKEKX OS OMe XXX ffi E ΓΛ Uh u ro Uh u X Ph X — ffi tu s <υ OMe OMe (U s 0> s 1 1 &quot ; < XXX 荽娲41 ^ 寸 inch m 1—^ in m F丨H m y_H 卜m 〇〇m ON o inch-丨H inch (N inch - 1 H m inch f Ή inch inch i-Η inch f Ή 卜 inch oo inch r —H 200902505

Physical data CO pei C(S)-NH-Me C(S)-NH-Me C(S)-NH-Me C(S)-NH-Et s© 13⁄4 ch2f chf2 (U s ID PH K ffi ffi ffi m [X( Pi K b EXi u ei KX a *<〇Os inch〇»Ti r-H r 1 H (N i-H 200902505 Preparation of starting material > 1-[(18)-1-benzene Ethylethyl]-4,5-dihydro-1,3-oxazol-2-amine

0^'"« Step 1: Dissolve 6.1 g (50.3 mmol) of phenylethylamine [CAs 2627-86-3] and 5.6 g (55,3 mmol) of triethylamine in 45 ml In the dichlorohydrazine, 5.8 g (22.6 mmol) of 2-chloroethyl isocyanate was added dropwise. The mixture was allowed to react at 20 ° C for 15 hours. Evaporation of all the volatile components gave 1-(2-chloroethyl)-3-[(ls)-l-phenylethyl]urea (i 〇gp = 1.76) and was used without further purification In step 2. Step 2: 11.4 g (50.3 mmol) of ^(2-fluoroethylphenylethyl)urea and 9.6 g (63 mmol) of 1,8-diazabicyclo[5 4.〇] eleven The _7-ene (DBU) was heated to 6 Torr in 50 ml of acetonitrile. The oxime was evaporated to dryness. The residue was dissolved in ethyl acetate and washed three times with water. After evaporation, it was evaporated to give &[(!§)_!_phenylethyl]-4,5-dihydro-1,3-oxazol-2-amine (79% of theory). -NMR (DMSO-dg) 4·61 quartet) 82 200902505 Biological example Example 1 Myzus test (spray treatment) Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethyl carbamide emulsifier : 0.5 parts by weight of an alkylaryl polyglycol ether for the preparation of a suitable active compound, 1 part by weight of the active compound being mixed with the amount of solvent and emulsifier, and the concentrate diluted with water containing an emulsifier To the desired concentration. The green compound dish of each growth stage (Afyzws cabbage disc) is sprayed with the desired concentration of the active compound preparation. After the required time, the measurement effect %, 100% table All mites were killed; 0% means no mites were killed. In this test, for example, the following compounds of Table 1 showed at least 80% activity at a concentration of 500 g/ha: Compound No. 1, 2, 3, 4, 5, 37, 38. Example 2 Tetranychus test, OP-resistance (spray treatment) Solvent: 78 parts by weight of acetone 1.5 parts by weight of decylguanamine emulsifier: 0.5 part by weight of alkyl group The aryl polyglycol ether is prepared as a suitable active compound preparation, 1 part by weight of the active compound 83 200902505 is mixed with the solvent and emulsifier of the amount, and the concentrate is diluted with the emulsifier-containing water to the desired concentration. The bean strain (10) vw/garb), which is parasitic with the greenhouse red deficiency 1 spider end of each growth stage, is sprayed with the active compound preparation at the desired concentration. After the required time, the % effect was measured, 100% means that all spider mites were killed; 0% means that no spider mites were killed. In this test, for example, the following compounds of Table 1 showed at least 80% activity at a concentration of 100 g/ha: Compound Nos. 1, 3, 4, 5, 38. Example 3 Aphis gossypii - test solvent: 7 parts by weight of dimethyl decylamine emulsifier: 2 parts by weight of aryl aryl polyglycol ether to prepare suitable active compound preparation, 1 part by weight of activity The compound is mixed with the amount of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing the emulsifier. If necessary, an ammonium salt or ammonium salt and an osmotic promoter are added to the desired concentration. The preparation of the active compound of the desired concentration of cotton plants (GoMjpiwm / i/rswiwm) is soaked. After a certain time, the lethality is measured, 100% means that all the mites are killed. 0% means that no aphids were killed. 84 200902505 In this test, the following compounds obtained from the preparation examples showed a good activity of 280% at an application rate of 4 ppm: Example 4 In this test, for example, the following compounds were A good activity of 280% was shown at an application rate of 20 ppm: Compound No. 1, 5, 38. Example 4 Myzus persicae · Test solvent: 7 parts by weight of decyl decylamine emulsifier: 2 parts by weight The aryl aryl polyglycol ether is prepared as a suitable active compound preparation, 1 part by weight of the active compound is mixed with the amount of solvent and emulsifier, and the concentrate is diluted with the emulsifier-containing water to the desired concentration. If necessary, add an ammonium salt or ammonium salt and a penetration enhancer to the desired concentration. Soak the treatment with the active compound of the desired concentration, which is severely irritated by Myz (10) parasitic Chinese cabbage pe/anensis After a certain time, the lethality was measured, 100% means that all aphids were killed; 0% means that no aphids were killed. In this test, the following compounds obtained from the preparation examples showed 280 at an application rate of 20 ppm. Good activity of %: Compound No. 1, 2, 4, 5, 38. 85 200902505 Example 5 Musca domestica - Test solvent: Dimethyl sulfoxide is a preparation of a suitable active compound, 10 The milligram of active compound is dissolved in 0.5 ml of solvent and the concentrate is diluted with water to the desired concentration. Before the test, a kitchen sponge is dipped in a mixture of sugar and compound solution and placed in a container. The container is sealed with a perforated lid. After a certain time, the % lethality is measured, 100% means that all house flies are killed; 0% means that no housefly is killed. In this test, for example, the following compounds are at 100 ppm The application rate shows a good activity of 280%: Compound No. 38. Example 6 Lucilia cuprina - Test solvent: Dimercaptocarboxamidine is a preparation of a suitable active compound, which is activated by 10 mg. Dissolve in 0.5 ml of solvent and dilute the concentrate to the desired concentration with water. Transfer about 20-30 green fly larvae cwpr/πβ/flrvae) to a test tube containing 1 cubic centimeter of ground horse meat and 0.5 ml. An aqueous dilution of the test compound. After a certain time, the lethality was measured, 100% means that all larvae were killed; 0% means that no larvae were killed. 86 200902505 In this test, for example, the following compounds showed a good activity of 280% at a 100 ppm application rate: Compound No. 38. Example 7 Boophilus microplus - test (injection) Solvent: dimethyl hydrazine is a preparation of a suitable active compound, 10 mg of the active compound is dissolved in 0.5 ml of solvent, and the concentrate is diluted with water. To the desired concentration. The compound solution was injected into the abdomen of five adult female wall w/cro/?/(10)) adults. The wall is transferred to a replica disk and cultured in a climate chamber for a period of time. The egg stock of the hatching eggs was monitored after 7 days. After a specific time, the lethality was measured, 1% 表示% means that all eggs were not hatched and killed; 0% means all eggs hatched. In this test, for example, the following compounds showed > 80% good activity at an application rate of 20 μg/animal: Compound No. 3, 5, 38. Comparative Biological Example 1 Peach test (MYZUPE spray treatment) Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethyl carbamide emulsifier: 0.5 part by weight of alkyl aryl polyglycol ether 87 200902505 For the preparation of the active compound, 1 part by weight of the active compound is mixed with the amount of solvent and emulsifier, and the concentrate is diluted with the emulsifier-containing water to the desired concentration. The preparation of the active compound of the desired concentration of the green cabbage disk of Afyzwi1 is sprinkled with each growth stage. After the required time, the % effect is measured, 100% means that all the mites are killed; % indicates that no aphids have been killed. In this test, for example, the following compounds of Table 1 show superiority to the prior art: see Table 2. Fantasy 2 leaf test; OP-resistant (TETRUR spray treatment) Solvent: 78 weight 1.5 parts by weight of acetone dimethyl carbamide emulsifier: 0.5 parts by weight of alkyl aryl polyglycol ether is a preparation of a suitable active compound, 1 part by weight of active compound and the amount of solvent and emulsifier Mix and dilute the concentrate to the desired concentration with water containing emulsifier. Spray the desired concentration of the bean leaf (6) vwfeflni) on the disk of the greenhouse red stalk Preparation of the compound. After the desired time, the measurement effect % '100% means that all spiders were killed; 0% means that no spiders were killed. 88 200902505 In this test, for example, the following compounds of Table 1 show superiority to the prior art: see Table 2. Table 2 Comparative Example Compound 1. MY Spray gram / ZUPE Application % 6 days 2. ΎΕ 1 Spray gram / hectare "RUR application % 6 days 2 According to the invention (Table 1) 20 100 100 70 B49 According to WO2006/127426 Page 48 20 0 100 0 89

Claims (1)

200902505 X. Patent application scope: 1. Compound of formula (I) (I) wherein R1, R2, R3, R4 and R5 independently of each other represent hydrazine, halogen, hydroxy, alkyl, alkoxy, i-alkyl, alkoxyalkyl, cycloalkyl, cyanogen, halogen Oxygen, sulfur-burning group, ||sulfuryl group, alkyl group, decyl group, decyloxy group, calcinyl group, calcinyl group, alkoxycarbonyl group, ethyl hydrazine Base, alkylcarbonyl, alkenylcarbonyl, pentafluorosulfonyl, amine, mono- and dialkylamino, cycloalkylamino, alkenyl, alkenyl, alkynyl, alkynyl, cyano or nitrate Or, independently of each other, an aryl, aryloxy or heteroaryl group optionally having one or more selected from halo, alkyl, alkyl, alkoxy, haloalkoxy, alkoxycarbonyl Substituents for nitro and cyano are substituted; r6 represents alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl or alkynyl, or represents aryl, a heteroaryl or heterocyclic group optionally substituted with one or more substituents selected from the group consisting of _, alkyl, alkoxy, nitro and cyano; R7 represents argon, alkyl or halo; r8 Represents -c(z)r10, -C(Z)OR10 , -C(Z)NR"R12 or -p(z)r13r14; 90 200902505 z represents o or s; R1() represents c!-c2 alkyl; R11 represents cvq alkyl; R12 represents hydrogen or cvq alkyl; And 2 R13 and R14 each represent a Cl_C2 alkoxy group or a Ci_C2 haloalkoxy group. A compound according to the formula (1) of claim i, wherein R, R2, R3, R4 and R5 independently of each other represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, alkoxyalkyl, naphthenic , haloalkoxy, alkylthio, iialkylthio, alkylsulfonyl, alkylsulfonyloxy, haloalkylsulfonyl, alkoxycarbonyl, ethylidene, alkylcarbonyl, Alkenylcarbonyl, dialkylamino, cycloalkylamino, alkenyl, alkenyl, block, block, cyano or nitro; R represents alkyl, haloalkyl, cycloalkyl, alkoxyalkane a group, an alkylthiolalkyl group, an alkenyl group or an alkynyl group, or an aryl group, optionally substituted with one or more substituents selected from the group consisting of: R represents hydrogen or daunyl; represents -C(0 R1(), -C(0)0R1(), -C(S)NR"R12 or -P(S)R13R14; Rl() represents CVC2 alkyl; RU represents CVC2 alkyl; 12 represents hydrogen or cvq alkane And 3 R and 尺 14 each represent a Cl_c2 alkoxy group or a fluorenyl alkoxy group. • A compound of the formula (1) according to claim 1 or 2, wherein R, R, R3, R4 and R5 independently of each other represent hydrogen, halogen, alkyl, alkoxy or ketone; 91 200902505 r6 represents An alkyl or _alkyl group, or an aryl group, optionally substituted with one or more substituents selected from halogen; R represents hydrogen; R8 represents -C(0)R10, -CXCOOR1. , -C(S)NRUR12 or -P(S)R13R14; R1() represents cvq alkyl; R11 represents Ci-c2 alkyl; R12 represents hydrogen; and R13 and R14 independently of each other represent alkoxy. 4. The compound of formula (I) according to any one of claims 1 to 3, wherein R1, R2, R3, R4 and R5 independently of each other represent hydrogen, halogen, alkyl, alkoxy or alkenyl R6 represents an alkyl group; R7 represents hydrogen; r8 represents -c(s)nrur12 or -P(S)RnR14; R11 represents c"c2 alkyl; R12 represents hydrogen; and R13 and R14 stand independently of each other (^-( Alkoxy. A method of preparing a compound of the formula (I) according to any one of claims 1 to 4, wherein R8 is -C(S)NRnR12 and R12 is hydrogen, wherein ) compound 92 200902505 R6 Ν R5 R > R7 N' H (II) wherein R1, R2, R3, R4, R6, R7 and r9 are as defined above, with thiocarbonyldiimidazole v\N〇S and compound RU of formula (III) NH2 (III) wherein R11 is reacted in an aprotic solvent as defined above. A composition comprising at least one compound of the formula (I) according to any one of claims 1 to 4 and a conventional extender and/or surfactant. 7. A method of controlling pests, which is based on the scope of the patent application! The compound of the formula (1) according to any one of the four items or the composition according to item 6 of the scope of the patent application acts on pests and/or their habitats. 8--A type according to any one of items i to 4 of the patent application or a composition according to item 6 of the patent application scope for controlling pests σ 93 200902505 VII. Designated representative map: (1) Representative of the case The picture shows: the (none) picture. (2) Simple description of the symbol of the representative figure: No. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: No 10% 11200902505 IX. Description of the invention: 1-—【Technical field to which the invention belongs The present invention relates to insecticidal derivatives of novel substituted phenylalkylamines, to methods of their preparation, and to their use for controlling animal pests, particularly arthropods, particularly insects. [Prior Art] A benzylamino heterocyclic derivative of the insecticidal and arachnid of the following formula is disclosed in WO 2006/127426 as a specific example (see, for example, Formula IB, page 8) R\R- N=< N- ίο R1 〇- 15 wherein R is a 1-naphthylphenyl group R1 is selected from hydrogen selected from the group consisting of cyanobenzyl, phenyl or one or two selected from halogen or (CkQ) alkyl Taking (CVC4)alkyl and (CVC2)haloalkyl; R2 is hydrogen; R5(CVC2)alkoxy(CVC2)alkyl, ((Ci-cy alkoxy R\X i?-p, , -co- 11- X Η (1) (3) X — sN(〇) 5a II -R16 (6) (7) -R 11 X -N-R13 R14 (5) FN—R 19 (9) 200902505 5 10 where X is oxygen Or sulfur; R7 and R8 are (Cl_C2) morpho are hydrogen; R11 is (crc4) alkyl; Ru is 乂 phase alkyl; r10 (CA) alkyl; a is 2; Rl5 is (CVc Chengji 2 ^ R14 is nitrogen or a group; R6 is (c-c2) alkyl or (cvc2) alkoxy: dialkylamine alkyl or (CVC2) alkoxy; 'and R is ... broad) Precondition is when naphthalene And r5 is a formula (5) (wherein R14 is hydrogen), wherein R1 is a (Cl-C2) alkyl group; and ♦ horse sulfur, R 3 is a methyl group and a phenyl group and R1 is hydrogen, R5 is (5) (wherein χ is gas, 夂 chloro-2-methyl is hydrogen) or formula (6) (where a is 2 and R15 is fluorenyl) except that methyl is methyl and R14 However, there is a continuing need for a It is known that it is incorporated into ^Yinyi, especially more novel (4) m killing = full and more convenient [inventive content] field agent. The present invention now provides a novel compound of formula (1) r»1 r>6 * _ 15 Wherein R1, R2, R3, R4 and R5 independently of each other represent hydrogen, halogen, thiol, alkyl, alkoxy, dentate, alkoxyalkyl, cycloalkyl, cyanogen, and oxygenated Base, alkylthio, haloalkylthio, alkylsulfonyl, alkylsulfonyloxy, halogenated sulphate, sulphur-based yellow oxygen, alkoxy, ethyl , alkyl group, benzyl group, pentafluoro extender, amine group, mono- and di-honey amine (I) 6 20