TW200800026A - Substituted 6-phenyl-7-amino-[1,2,4]-triazolo[1,5-a] pyrimidines and their use for controlling harmful fungi - Google Patents

Abstract

The present invention relates to substituted 6-phenyl-7-amino-[1,2,4]-triazolo[1,5-a]-pyrimidines of the formula I and their agriculturally acceptable salts and their use for controlling harmful fungi. The invention also relates to compositions comprising at least one substituted 6-phenyl-7-amino-[1,2,4]-triazolo[1,5-a]pyrimidine of the formula I or an agriculturally acceptable salt thereof. In formula I, the substituents are as defined below: R1 is optionally substituted C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl or phenyl, naphthyl, or a five-or six-membered heterocycle which comprises one, two, three or four heteroatoms from the group consisting of O, N and S, R2 is hydrogen or one of the groups mentioned for R1, L1 is C1-C4-alkyl or C1-C4-alkoxy, L2 is fluorine, chlorine or C1-C4-alkyl, X is halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C2-haloalkoxy.

Description

200800026 IX. DESCRIPTION OF THE INVENTION: TECHNICAL FIELD OF THE INVENTION The present invention relates to substituted 6-phenyl-7-aminotriazolo[l,5-a]pyrimidines and their use in controlling harmful fungi. The invention is also directed to compositions comprising at least one substituted 6-phenyl-7-aminotriazolo-[l,5-a] bite. [Prior Art] Substituted 6-phenyl-7-amino-[ΐ52,4]-triazolo[na]pyrimidines and their use in controlling harmful fungi have been described in various publications. In general, it is known from the European Patent No. A 71 792 and the European Patent No. A 55 〇 113 that the 5- gas-6-phenyl-7-aminotrisium sigma is sinusoidal. WO 99/48893 describes the use of 6-(2-halo-4-alkoxyphenyl)-7-amino-[1,2,4]-triazentidine for the control of harmful fungi. WO 03/93271 describes the use of 6-(2•halo-4_alkylphenyl)-7-amino-[1,2,4]-triazolo-[u'aj pyrimidine for the control of harmful fungi. _ US Patent No. 6,204, 2.69 describes an optically active amine with a palmitic 2'2'2 fluoro"-l-(Ci-C4_alkyl)ethyl group at the 7-amine nitrogen Base_% halogen-6-phenyl[1,2,4]-triazolo[i,5-a]-pyrimidine. In particular, WO 02/02563 proposes a compound for the control of tumors 5-chloro-6-(2,5-difluoro-4-indolyloxyphenyl)-7-((1,2,2-trimethylpropane-^) Amino))[1,2,4]three alpha sits and _[i,5_a]p 唆. However, the / tongue properties of 6-phenyl-7-amino-[1,2,4]-triazolo-[i,5-a]pyrimidine are known to be unsatisfactory in many cases. Based on this, it is an object of the present invention to provide a compound having improved activity and/or a broader spectrum of activity 118620.doc 200800026. Surprisingly, a substituted 6-phenyl-7 of I [invention], The purpose and other objects can be attained by the formula 7-amino-[1,2,4]-trisino[i,5-a] stilbene described below. Use of sex fungi: Therefore, the present invention relates to substituted 6-phenyl-7 amino-[丨, 2,4b-tris-[l,5-a](iv) and its agriculturally acceptable Salt control: plant destruction

Wherein the substituents are defined as follows: R1 is cvc8_alkyl, Cl-c8-_alkyl, C3_C8jf, alkyl, C3-c8-halocycloalkyl, C2-C8-alkenyl, C2-(V halogen Alkenyl, c3-C6-cycloalkyl, C3-C6- _cycloalkenyl, c2-c8-alkynyl, C2-C8-haloalkynyl or phenyl, naphthyl or one containing 1, 2 3 or 4 heterocyclic rings derived from a hetero atom consisting of ruthenium, N and S, R2 hydrogen or one of the groups mentioned for R1, wherein the substituent R1 mentioned above And/or Han 2, 1, 2, 3 or 4 hydrogen atoms may be replaced by the same or different groups Ra:

Ra is a cyano group, a nitro group, a hydroxyl group, (VCV alkyl group, Ci-Cp halogenated leucoyl group, Ci-Ce aryl group, c3_C6-cycloalkyl group, CVCV alkoxy group, cvcv haloalkoxy group, Ci_C6_) Alkoxycarbonyl, cvcv thiol, cvcv alkylamino, di-Cl-C6-alkyl 118620.doc amine, C2-C8-alkenyl, c2-C8-haloalkenyl, c3-c8- Cycloalkenyl, C2-C6-alkenyloxy, c3_c6-haloalkenyloxy, C2-C6-alkynyl, C2-CV haloalkynyl, c3-C6-alkynyloxy, c3-c6-haloalkyne Oxy, CrC6-cycloalkoxy, c3-C6-cycloalkenyloxy, oxy-Ci-C: 3-aralkyloxy, phenyl, naphthyl, one containing 1 to 4 from 〇, N And a 5 to 10 membered saturated heterocyclic ring of a hetero atom of the group consisting of s, wherein the aliphatic, cycloaliphatic or aromatic moiety may be partially or fully halogenated or may carry 1, 2 or 3 groups Rb : R is a cyano group, a nitro group, a thiol group, a sulfhydryl group, an amine group, a carboxyl group, an aminocarbonyl group, an aminothiocarbonyl group, an alkyl group, a halogenated alkyl group, an alkenyl group, an alkenyloxy group, an alkynyloxy group, an alkoxy group. , haloalkoxy, alkylthio, alkylamino, dialkylamino, fluorenyl, alkylcarbonyl, alkylsulfonyl, alkyl Anthracenyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, wherein the alkane in the group The group contains 1 to 6 carbon atoms and the alkenyl or alkynyl group mentioned in the groups contains 2 to 8 carbon atoms; and/or 1 to 3 or less groups: a cycloalkyl group, a cycloalkyloxy group a heterocyclic group, a heterocyclic oxy group, wherein the ring system comprises 3 to 1 ring members; aryl, aryloxy, arylthio, aryl-Ci-Cr alkoxy, aryl-Ci- C6-alkyl, heteroaryl, heteroaryloxy, heteroaromatic sulfur 200800026, wherein the aryl groups preferably comprise from 6 to 1 ring members, the heteroaryl groups comprising 5 or 6 a ring member, wherein the ring systems may be partially or fully substituted by a tooth or may be substituted with a burnt or a dentate group;

Or R1 and R2 together with the nitrogen atom to which they are attached may also form a 5- or 6-membered heterocyclic ring which is linked via nitrogen and further contains ^, 2 or 3 groups consisting of 〇, ^s A hetero atom is a ring member and may carry 1, 2, 3 or 4 substituents from the group consisting of: a pixel, a Ci_C6_alkyl group, a Ci_C6_haloalkyl group, a c2-C6-alkenyl group , C2_C6_haloalkenyl, Cl·c6-alkoxy, Cl_c6-haloalkoxy, alkenyloxy, C3-C6-!S-alkenyloxy, (exo)_Ci_c6-alkylene and oxy-Ci -Cs-Extended alkoxy; Cnc4-alkyl or C^CV alkoxy, fluoro, gas or C^Czr alkyl, phenyl, cyano, CKC4-alkyl 'Cl_c4_haloalkyl CieCV is an alkoxy halogenated alkoxy group; wherein when R2 is hydrogen and X is halogen, R1 is not a group of the formula CH(CF3) gas Ci_C4_alkyl). The present invention also relates to the above formula: 6 phenylamino hydrazino, 2,4]-triazolo[l,5-a]pyrimidine and an agriculturally acceptable salt thereof, wherein R1 is a formula cH(CF3) a group of _(Ci C4 alkyl), a compound of the formula I wherein R2 is hydrogen and an X-based halogen, and a salt thereof, and further a compound 5-chloro-6 乂2,5-difluoro-4-methoxyphenyl )_7_((1,2,2-dimercaptopropen-1-yl)amino)-[1,2,4]triazolo-[1,5-uracil and I18620.doc -9- 200800026 Except salt. The present invention also relates to the following 6-phenyl-7-amino-triazolo[l,5-a]pyrimidine and its agriculturally acceptable salt··5-chloro-6-(2,5- Difluoro-4-methylphenyl)-7q(2,2,2-trifluoro-l-methylethyl)amino)_[1,2,4]di-sigma-[l,5- a] bite; -5-mercapto-6-(2,5-difluoro-4-methylphenyl)-7-((2,2,2-trifluoro-1-methylethyl)amine )[1,2,4]triazolo-[i,5_a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methylphenyl)-7-(2 , 2,2-trifluoro-i-mercaptoethyl)amino)-[1,2,4]triazolo-[i,5-a]pyrimidine; -5-methoxy·6-(2,5 -difluoro-4-methylphenyl-7-((2,2,2-trifluoro-fluorenylfluorenyl)-amino)-[1,2,4]triazolo-[i, 5-a]pyrimidine; -5-methyl·6-(2,5-difluoro-4-decyloxyphenyl)-7-((252,2-trifluoro-1_methylethyl)- Amino)-[1,2,4]triazolo-[15-a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methoxyphenyl)_7-(2 , 2,2-trifluoroq-methylethyl)-amino)-[1,2,4]triazolo-[i,5-a]pyrimidine; _ 5-decyloxy-6-(2 ,5-difluoro-4-methoxyphenyl)-7-((2,2,2-trifluoro_1-decylethyl)-amino)-[152,4]triazolo-[1 ,5-&pyrimidine And the use thereof for controlling plant destructive fungi. The invention further provides a method for controlling a plant damage (= phytopathogenic) fungus, wherein an effective amount of at least one of the formulas "the compound and the agriculturally acceptable Salt treating the fungus or material, plant, soil or seed to be protected from fungal attack. The invention further provides a composition suitable for controlling a harmful fungus, the composition comprising at least one compound of the formula I and/or An agriculturally acceptable salt thereof and at least one liquid or solid carrier. 118620.doc -10- 200800026 The present invention additionally provides preferably from 1 g/100 kg of seed to (7) g / g (9)

The amount of the seed contains at least one seed of the formula [the compound and/or its agriculturally acceptable salt 2). X The salts which are useful in agriculture are, in particular, the salts of their cations or the acid addition salts of these acids which do not adversely affect the fungicidal action of the cations and anions of the compounds of the formula I, respectively. Therefore, suitable cations are particularly selected from the group consisting of alkali metals, preferably sodium and unloading; alkaline earth metals, preferably calcium, barium and strontium; transition metals, preferably manganese, copper, zinc and iron; and (if needed) Ammonium ion having up to 4 6-(:4-alkyl substituents and/or a phenyl or a benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium , trimethylbenzylammonium; additional scaly ion; cerium ion, preferably tris(Ci_C4_alkyl) fluorene; and oxonium ion, preferably tris(C^CU-alkyl) oxonium. The anions of salt formation are mainly chloride, bromide, fluoride, hydrogen sulfate, sulphate, sulphate, acid nitrogen, sulphate, nitrate, bicarbonate 'carbonate, six An anion of fluorite, hexahydrate, benzoate anion and Cl_C4·alkanoic acid (preferably formate, acetate, propionate and butyrate) 1 is formed by reacting with a corresponding anionic acid (preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid). The variables given in the above formula are determined. In the above, a general term is used, which is usually a representative of the substituent. The term ^^ denotes the number of possible carbon atoms in the substituent or substituent moiety in each case: halogen: fluorine, chlorine, bromine and iodine Alkyl·saturated linear or branched hydrocarbon having from 1 to 4, 6 or 8 carbon atoms 118620.doc -11 · 200800026 Group 'for example 'Ci-C6_alkyl group' eg thiol, B Base, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-mercaptopropyl, iota; μ dimethylethyl, pentyl, 1-decyl butyl, 2 -methylbutyl, 3-nonylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, dimethylpropyl, 1,2-dimercaptopropyl, 1- Methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-mercaptopentyl, 1,1-dimethylbutyl, it-didecylbutyl, '-decylbutyl, 2,2·dimercaptobutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, hydrazine, 2_ Trimethyl propyl, ^ H2-dimethylpropyl, 1-ethyl-1-mercaptopropyl and 1-ethyl-2-mercaptopropyl; haloalkyl · 1 to 2 4, 6 or 8 a linear or branched alkyl group of a carbon atom (as described above) wherein some or all of the hydrogen atoms of the group may be replaced by a halogen atom as described above: especially a Cl_c2_haloalkyl group, such as a chloroantimonyl group, bromine Sulfhydryl, digas sulfhydryl, trimethylmethyl, fluoroindolyl, difluoromethyl, trifluoromethyl, fluorofluoromethyl, difluorofluoroindolyl, chlorodifluoroindolyl, "sweet fluoroethyl, 1-, / stinky ethyl, 1-decylethyl, 2-fluoroethyl, 2,2-di-Iethyl, 2,2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 2-Chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and '1,1,1_three Fluoropropan-2-yl; 'alkenyl: an unsaturated straight or branched hydrocarbon group having 2 to 4, 6 or 8 carbon atoms and 1 or 2 double bonds at any position, for example, ^_(^_Alkenyl group such as vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentene 118620.doc -12- 200800026, 2-pentyl Alkenyl, 3-pentenyl, 4- Alkenyl, 1-methyl-1-butenyl, 2-mercapto-1-butenyl, 3-mercapto-1-butenyl, U-mercapto-2-butenyl, 2-methyl 2-butenyl, 3-mercapto-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-mercapto-3-butene 1,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, L2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1 -ethyl-2.propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexyldecyl, 1-methyl-1-pentenyl, 2-mercapto-1-pentenyl, 3-mercapto-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-nonenyl, 2-methyl-2 -pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-decyl-3-pentenyl, 2-mercapto-3-pentenyl, 3 -mercapto-3-pentenyl, 4-mercapto-3-nonenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4- Pentenyl, 4-mercapto-4-pentenyl, l,l-dimercapto-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl 1-butenyl, 1,2-dimercapto-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1 , 3·2 2-butenyl, 1,3-dimethyl-3-butenyl, 2.2-dimercapto-3-butenyl, 2,3-dimercapto-1-butenyl, 2, 3-dimethyl-2-butenyl, 2,3-dimercapto-3-butenyl, 3,3-dimethyl-1-butenyl, 3.3-dimethyl-2-butene Base, 1-ethyl-1-butenyl, ethylbutenyl, 1-ethyl-3-butanyl, 2-ethyl-1-butenyl, 2-ethyl-2-butene , 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-l-decyl-2-propenyl, 1-ethyl-2 -Methyl-1-propenyl, 1 ethylmethyl-2-propenyl; haloalkenyl: 1 or 2 double bonds having 2 to 8 carbon atoms and located at any position as described above a saturated linear or branched hydrocarbon group wherein some or all of the hydrogen atoms of the group 118620.doc -13 - 200800026 are replaced by the above halogen atoms (especially fluorine, chlorine and bromine);

Alkynyl: a straight or branched hydrocarbon group having from 2 to 4, 6 or 8 carbon atoms and at any position or two triple bonds, for example, c2_c6-alkynyl, for example ethynyl, 1- Propynyl, 2-propynyl, ^butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, indolyl, pentynyl, 3 _Pentynyl, 4-pentynyl, 1-indolyl-2-butynyl, hydrazino-3-butynyl, 2-methyl-3-butynyl, 3-methyl-hydrazine Alkynyl, dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 'hexynyl, 5-hexyl Alkynyl, i-methyl Ipentynyl, 丨-methyl:pentynyl, methyl-4-pentynyl, 2-mercapto-3-pentynyl, methylpentynyl, 3-methyl Small pentynyl, 3-methyl-4-pentynyl, 4-mercapto + pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, ^ Dimethyl_3_butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-diindenylbutynyl , 1-ethyl-2-butynyl, bethyl-3-butynyl, ethyl-3-butynyl and 1-ethyl-fluorenyl-2-ylpropynyl; cycloalkyl: I There are 3 a monocyclic or bicyclic saturated group of 6 or 8 carbon ring members, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group; an alkylthio group: the above Ci_Cp alkyl group bonded via a sulfur atom; Sulfhydryl (also known as alkyl): the above-mentioned alkyl group attached via a so group; alkyl group: the above-mentioned term 5 to 1G heterocyclic ring bonded via 10) 2 hydrazine Or a 5-membered or heterocyclic ring containing a saturated or partially unsaturated heterocyclic group having 5 or 6 118620.doc -14-200800026 and 5, 6, 7, 8, 9 or 10 atoms as ring members, respectively And an aromatic heterocyclic group (heteroaryl), wherein 丄, 2 3 or 4 of the atoms are derived from a hetero atom of a group consisting of 0, N and s, wherein the heterocyclic groups are specifically There are 1, 2, 3 or 4 nitrogen atoms or 1 or 2 heteroatoms selected from oxygen and sulfur and, if appropriate, another hydrazine or 2 heteroatoms selected from nitrogen as ring members. These include, inter alia: a 5, 6 or 7 membered heterocyclic group containing from 1 to 3 nitrogen atoms and/or 1 oxygen or sulfur atom or 2 or 2 oxygen and/or sulfur atoms, for example 2 to tetrahydrofuranyl, 3_tetrahydrofuranyl, 2-tetrahydrothiophenyl, 3-tetrahydrothiophenyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-iso Oxazolidine, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidine, 2-ox Zyridinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolyl, 4-thiazolidinyl, 5-oxazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2 - pyrroline 2 base, bilorin-3-yl, 3_σ bilorin-2-yl, 3_吼洛琳_3-yl, 2_hexahydro. Bipyridyl, 3-hexahydropyridyl, 4·hexahydropyridyl, 1 decyl-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiophenyl '3-Hexhydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl and 2-piperidinyl; 5, 6 or 7-membered a ring group which is bonded via a nitrogen and which, in addition to a carbon ring member, also contains L, 2 or 3 nitrogen atoms or i, 2 or 3 nitrogen atoms and 1 sulfur or oxygen atom as a ring member, for example 1 - η is more than a bite base, 3 - ° is more than 嘻 · 1-l base, 丨 嗤唆 嗤唆 、, 2-imiline-1-yl, 1-hexahydro π 唆 、, 1 _ _ p well base, Benzinyl, thiomorpholin-4_yl and 4H-1,3,4-thiadiazin-4-yl; 118620.doc 200800026 - contains 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and / Or a 5-membered heteroaryl group of a sulfur or an oxygen atom: a 5-membered heteroaryl group which may have 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom as a ring member in addition to a carbon atom, For example, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-indolyl, 3- σ 峻 基, 4-11 fluorenyl, 5-° fluorenyl ,2-. Oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl and 1,3,4-triazole-2 a 5-membered heteroaryl group which is attached to the nitrogen and which, in addition to the carbon ring member, also contains 1, 2, 3 or 4 nitrogen atoms as a ring member, for example, 1 Η-pyrrol-1-yl, 1 Η-pyrazolyl, 1 Η -Saliva-1-yl, 1,2,3-tris-s-l-yl, 1,2,4-tris-1-yl, 1-tetrazol-1-yl and 2Η-tetrazole·2· a 6-membered heteroaryl group containing 1 to 3 or 1 to 4 nitrogen atoms: a 6-membered heteroaryl group which may have 1 to 3 or 1 to 4 nitrogen atoms as a ring member in addition to a carbon atom, for example 2-吼, 3-吼, 4-吼, 3-oxazinyl, 4-oxazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl Stretching base: a divalent unbranched chain containing 1 to 6 CH2 groups, such as ch2, ch2ch2, ch2ch2ch2, ch2ch2ch2ch2, CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2; oxyalkylene: one of the valences is attached to the backbone via an oxygen atom; a divalent unbranched chain containing 2 to 4 CH2 groups, for example, 〇CH2CH2, och2ch2ch2aoch2ch2ch2ch2; oxyalkyleneoxy: The two valencies are linked via an oxygen atom to a divalent unbranched chain of the backbone containing from 1 to 3 CH2 groups, such as 〇c 〇, 118620.doc -16 - 200800026 OCH2CH2 〇 and 〇CH2CH2CH2 〇. The scope of the present invention includes the compounds of the formula having a palmitic center and the (S)-isomers and racemates. In view of the intended use of the triazolopyrimidines of formula I, the following meanings of the substituents are preferred, and in each case they are used independently or in combination: L1 in formula I is preferably CVC4-alkoxy, Especially oxime. The latter is also a compound of the formula wherein the L1 system is C^C4.alkyl and especially the thiol group. L2 is preferably a fluorine, gas or sulfhydryl group and is especially fluorine. According to a first preferred embodiment, L1 is a decyloxy group and l2 is a fluorine. According to a second preferred embodiment, Li is a fluorenyl group and a B is a system I. R1 is preferably C4-C8-alkyl, c3_c8-cycloalkyl, C3_C8-halocycloalkyl, c3-c8-alkenyl, C3-C8-halogenated, C3_C6_cycloalkyl, C3_C6_halo Cycloalkenyl, Q-C8-alkynyl, C^C8-self-alkynyl or phenyl, naphthyl or a hetero atom comprising 1, 2, 3 or 4 from a group consisting of 0, N and s A 5- or 6-membered heterocyclic ring in which 1, 2, 3 or 4 hydrogen atoms in the group 1, can be substituted as described above. Among them, preferred are the following compounds: wherein R1 is C4-C8-alkyl or C3-C8-alkenyl and is especially selected from CH2CH(CH3)2, CH(CH3)-CH2CH3 > CH(CH3)- CH(CH3)2 > CH(CH3)-C(CH3)3 > CH2CH=CH2 and ch2c(ch3)=ch2 group. A particularly preferred embodiment relates to a compound of formula I wherein R2 is hydrogen, methyl or ethyl; and R1 is C4-C8-alkyl, c3-c8-alkenyl, Cl_c2_ by alkyl or c3_c6. 118620.doc 200800026 A cycloalkyl group, wherein such groups may, when appropriate, carry one of the following groups: R-based murine, nitro, thiol, Ci-C6-alkyl-based thio, C3-C6- Cycloalkyl, CVC6-alkoxy, cvc6-alkoxycarbonyl, CV c6-alkylthio, Cl-C6-alkylamino, di-CVCV alkylamino, c3-c8-cycloalkenyl, C2 -C6-alkenyloxy, C3-C6-alkynyloxy, C^CV cycloalkoxy, c3-C6-cycloalkenyloxy, oxy-Ci-C3-alkylalkoxy, phenyl, naphthyl, a 5 to 10 membered saturated heterocyclic ring containing 1 to 4 hetero atoms derived from a group consisting of ruthenium, N and S, wherein the ring groups themselves may be partially or fully halogenated or may have 1 to 3 groups Group Rb. Wherein, preferred is a compound of the following formula j: wherein Ri is όνον, cvc:2·fluoroalkyl or C3_C8-alkenyl and is especially selected from CH2CF3, CH2CH(CH3)2, CH(CH3) A group consisting of -CH2CH3, ch(ch3)_ch(ch3)2, CH(CH3)_C(CH3)3, ch2ch=ch2, and CH2C(CH3)=CH2. Among them, preferred are also compounds of the formula I in which the 2NR1R2 group of the formula I is a group of formula A:

H3C I (a) wherein G is a CrC6-alkyl group, especially ethyl, n-propyl and isopropyl, normal, second and third butyl; and alkoxymethyl, especially ethoxymethyl; C^C6-cycloalkyl, especially cyclopentyl or cyclohexyl; R2 is as defined above, 118620.doc -18-200800026 and especially is a murine or sulfhydryl group, and # represents the point of attachment to the trisole. Preferred are also compounds of formula I wherein R1 is a group B:

F F

F---(CH2)-CHR- B Z1 Z2 wherein q is o or l; z1 is hydrogen, fluorine or fluoroalkyl, especially hydrogen, fluorine or trifluoromethyl, Z-hydrogen or IL, or z and Z together form a double bond; r3 is hydrogen or methyl. Further, 'preferably, the compound wherein R1 is a c3-c6-cycloalkyl group which may be substituted by a Ci-Cr alkyl group and especially a cyclopentyl group or a cyclohexyl group]. R2 is preferably hydrogen, CVC3-alkyl or CVC3-haloalkyl, especially hydrogen, methyl or ethyl. Particularly preferred are compounds of formula J wherein R2 is hydrogen. Preferred are likewise compounds of the formula I in which the R2 is decyl or ethyl. Preference is also given to compounds of the formula I in which Ri is 〇2_(:8-haloalkyl, especially c2_c8-fluoroalkyl and R2 is CVC3-alkyl or (VC3-haloalkyl, especially methyl or ethyl). Preferred is also a group wherein R1 is a formula B, especially 2,2,3,3,3-pentafluoropropyl or 2,2,33354,4,4-heptafluorobutyl and 2 is hydrogen A compound of formula 1 is also preferably a compound of formula I wherein R1 is a group of formula CH^CFsHCkCV alkyl) and especially CH(CF3)-(CH3). In such groups, the band 118620.doc - 19-200800026 A carbon atom having a CF3 group is palmarous and preferably has an s configuration. If R2 is hydrogen in the group, X is preferably selected from the group consisting of a cyano group, a CVC4-alkyl group, and a CVCV alkoxy group. And a group consisting of Cr-C2·halogenated alkoxy groups and especially selected from the group consisting of cn, methyl and methoxy. If R1 and/or R2 contain a haloalkyl or haloalkenyl group having a palmitic center, Preferably, the groups are (S)-isomers. For halogen-free alkyl or alkenyl groups having a palmitic center in Ri*R2, preferred is the (R) configuration. Isomers. Preferred are also compounds of formula I below: wherein R1 & R2 and The attached nitrogen atoms together form a 5 or 6 membered heterocyclic ring via a nitrogen linkage and which may further contain 1, 2 or 3 heteroatoms from the group consisting of 〇'N and S as ring members and which may carry i, 2, 3 or 4 substituents of the group consisting of: ginseng, (VCV alkyl, CVCV haloalkyl, C2-C6-alkenyl, c2-c6-haloalkenyl, Ci_C6-alkoxy , Ci_c6_haloalkoxy,

Cr alkenyloxy, CrC6-haloalkenyloxy, (exo)-Cl_C6-alkylene and oxy·Ci-C3-aralkyloxy. Wherein the 'preferably' is a compound of the formula: wherein R 1 & R 2 and the nitrogen atom to which they are attached together form a hexahydropyridinyl, morpholinyl or thiomorpholinyl ring, especially a hexahydropyridyl ring, wherein The group may carry i, 2 or 3 of the abovementioned substituents, especially those selected from the group consisting of halogen, Ci_C4_alkyl and Ci_C4_halogen. Particularly preferred are compounds wherein R1 and R2, and the nitrogen atom to which they are attached, form a 2-methyl-, 3-methyl- or 4-methylhexahydro-n-biter ring. Further, 'the best one is one in which R1 and R2 together with the nitrogen atom to which they are attached 118620.doc -20- 200800026 form one of the above five-membered saturated or unsaturated ring or morpholinyl or thiomorpholinyl ring. A compound wherein the rings are substituted with 3 halogens, Ci_C4_alkyl or CKC4-haloalkyl. Further, the present invention provides, in particular, a compound of the formula I in which Ri&R2 and the nitrogen atom to which it is attached form a pyrazole or pyrrolidine ring which may be passed through a ruthenium or a ruthenium ring. , Cl-C4_alkyl or Ci_C4-haloalkyl substituted, especially 3,5-dimethylpyrazole, 3,5-di-(trifluoromethyl)fluorene' 2-methylpyrrolidine or 3_ Methyl pyrrolidine. Among the compounds of the formula I, especially preferred are those in which the sage is a sulphur and especially the chlorin. Preferred are also Hb compounds of the formula X-based cyano group. The latter is also a compound of the formula I in which is a methyl group and especially a methyl group. Preferred are likewise compounds of the formula I in which the alkoxyhaloalkoxy group and especially the decyloxy or ethoxy group are attached. Especially preferred are compounds of Ι-Α, I-B, Ι-C and Ι-D:

F F

118620.doc -21- 200800026 wherein R1 and R2 are as defined above and are chloro, methyl, decyloxy or cn and are especially chloro or decyl, and agriculturally acceptable salts thereof. In particular, in view of its use, it is preferred to incorporate the compounds of the formulas in the table below. Further, the groups mentioned in the table which are suitable as a substituent are themselves (independent of the combination in which the groups are mentioned) are a preferred embodiment of the substituent. Table 1: Compounds of the formula Ι-A, wherein X is a gas and in each case the ... and R combinations of the compounds correspond to a row in Table A, except for the exclusion of the 5th, 54th and 57th. Table 2: Compounds of formula I-B wherein X is chlorine and in each case the combination of ... and R2 corresponds to one row in Table A, with exceptions 51, 54 and η excluded. Table 3: Compounds of the formula Ι-C, wherein X is chlorine and in each case the combination of the compounds 1 and R2 corresponds to a row in Table A, and the exceptions are excluded from the 5th, 54th and 5th. Table 4: Compounds of the formula Ι-D wherein X is chlorine and in each case the Ri and R2 combinations of the compounds correspond to a row in Table A, except for the exclusion of the 5th, 54th and 57th. Table 5: Compounds of Formula I-A wherein X is methyl and in each case the compound 1 and R2 combinations correspond to one row in Table A. Table 6: Compound of Formula I-B 'where X is methyl and the combination of R1 and R2 of the compound in each case corresponds to one row in Table A. I18620.doc -22- 200800026 Table 7 · Compounds of the formula ^, wherein the X-based thiol group and in each case the compound... and the R2 combination correspond to a row in Table A. Table 8: Compound of formula ^ wherein X is methyl and in each case the compound... and the R2 combination correspond to a row in Table A. Table 9: Compounds of the formula Ί-Α wherein the X-based cyano group and in each case the compound... and the R2 combination correspond to a row in Table A. Table 10 · Compounds of Formula I-B 'where X is a cyano group and in each case the compound... and the R2 combination correspond to a row in Table A. Table 11: Compounds of the formula Ι-C where X is a cyano group and in each case the combination of the size i and R2 of the compound corresponds to one row in Table A. Table 12: Compound of the formula Ι-D where X is a gas group and in each case the combination of r1 and R2 of the compound corresponds to a row in Table A. Table 13: Compounds of Formula I-A wherein X is a methoxy group and in each case the R1 and R2 combinations of the compounds correspond to a row in Table A. Table 14: Compounds of Formula I-B 'where X is methoxy and the R1 and R2 combinations of the compounds in each case correspond to one row in Table A. 118620.doc -23- 200800026 Table 15 · Compounds of the formula Ι-C, wherein X is a methoxy group and in each case the R1 and R2 combinations of the compounds correspond to a row in Table A. Table 16: Compounds of the formula Ι-D wherein X is a decyloxy group and in each case the " R1 and R2 combinations of the compounds correspond to a row in Table A. * Table A: No. R1 R2 A-1 ch3 H A-2 ch3 CHs A-3 ch2ch3 H A-4 ch2ch3 ch3 A-5 CH2CH3 CH2CH3 A-6 CH2CF3 H A-7 ch2cf3 CHs A-8 CH2CF3 CH2CH3 A-9 CH2CC13 H A-10 CH2CC13 CHs A-11 CH2CC13 ch2ch3 A-12 CH2CH2CH3 H A-13 CH2CH2CH3 ch3 A-14 ch2ch2ch3 ch2ch3 A-15 ch2ch2ch3 CH2CH2CH3 A-16 ch(ch3)2 H A-17 CH(CH3)2 CH3 A_18 CH(CH3)2 CH2CH3 A-19 CH2CH2CH2CH3 H A-20 CH2CH2CH2CH3 ch3 A-21 ch2ch2ch2ch3 CH2CH3 A-22 CH2CH2CH2CH3 ch2ch2ch3 A-23 C2CH2ai2CH3 CH2CH2CH2CH3 A-24 (soil) ch(ch3)-ch2ch3 H A-25 (soil CH(CH3)-ch2ch3 ch3 A-26 -24- 200800026

No. R1 R2 A-29 (s) CH(CH3)-CH2CH3 CH2CH3 A-30 (R) CH(CH3)-CH2CH3 H A-31 (R) CH(CH3)-CH2CH3 ch3 A-32 (R) CH( CH3)-CH2CH3 ch2ch3 A_33 (5) ch(ch3)-ch(ch3)2 H A-34 (5) ch(ch3)-ch(ch3)2 ch3 A-35 (s) ch(ch3)-ch(ch3)2 CH2CH3 A_36 (5) CH(CH3VCH(CH3)2 H A-37 (S) CH(CH3)-CH(CH3)2 ch3 A-38 (S) CH(CH3)-CH(CH3)2 CH2CH3 A-39 (R) CH(CH3)-CH(CH3)2 H A-40 (R) CH(CH3)-CH(CH3)2 ce3 A-41 (8) ch(ch3)_ch(ch3)2 ch2ch3 A-42 (v) ch(ch3) -c(ch3)3 H A-43 (earth) ch(ch3)-c(ch3)3 gh3 A-44 (earth) ch(ch3)-c(ch3)3 CH2CH3 A-45 (s) ch(ch3 )-c(ch3)3 H A-46 (s) ch(ch3)-c(ch3)3 ch3 A-47 (s) ch(ch3)-c(ch3)3 CH2CH3 A-48 (R) CH( CH3)-C(CH3)3H A-49 (R) CH(CH3)-C(CH3)3 ch3 A-50 (R) CH(CH3)-C(CH3)3 CH2CH3 A-51 (v) ch(ch3 )-cf3 H A-52 (士) ch(ch3)-cf3 ch3 A_53 (±) CH(CH3)-CF3 CH2CH3 A-54 (S) GH(CH3)-CF3 H A-55 (S) CH(CH3 )-CF3 ch3 A-56 (S) CH(CH3)-CF3 CH2GH3 A-5.7 (R) CH(CH3)-CF3 H A-58 (R) CH(CH3)-CF3 ch3 A-59 (R) CH (CH3)-CF3 CH2CH3 A-60 (±) CH(CH3)-CC13 H A-61 (earth) CH(CH3)-CC13 ch3 A-62 (soil) Ch(ch3)-cci3 CH2CH3 A-63 (S) CH(CH3)-CC13 H A-64 (S) CH(CH3)-CC13 ch3 A-65 (S) CH(CH3)-CC13 CH2CH3 A-66 ( R) CH(CH3)'CC13 H A-67 (R) CH(CH3)-CC13 ch3 A-68 (R) CH(CH3)-CC13 CH2CH3 A-69 CH2GF2CF3 H 118620.doc -25- 200800026 No. R1 Rz A-70 ch2cf2gf3 ch3 A-71 ch2cf2cf3 CH2CH3 A-72 CH2(CF2)2CF3 H A-73 ch2(cf2)2cf3 ch3 A-74 ch2(cf2)2cf3 CH2CH3 A-75 CH2C(CH3)=CH2 H A-76 CH2C(GH3)=CH2 ch3 A-77 CH2C(CH3)=CH2 CH2GH3 A-78 ch2ch=ch2 H A-79 ch2ch=ch2 CH3 A-80 ch2ch=ch2 CH2CH3 A-81 CH(CH3)CH=CH2 H A -82 ch(ch3)ch=ch2 ch3 A-83 ch(ch3)ch=ch2 CH2CH3 A-84 ch(ch3)c(ch3)=ch2 H A-85 CH(CH3)C(CH3)=CH2 ch3 A -86 CH(CH3}C(CH3)=CH2 CH2GH3 A-87 ch2-c=ch H A-88 CHrC Tri CH ch3 A-89 CHrC Tri CH CH2CH3 A-90 Cyclopentyl H A-91 Cyclopentyl ch3 A-92 cyclopentyl CH2CH3 A-93 cyclohexanyl H A-94 cyclohexyl ch3 A_95 cyclohexyl CH2CH3 A-96 ch2-c6h5 H A-97 ch2-c6h5 ch3 A-98 ch2-c6h5 CH2GH3 A-99 - ( CH2)2CH=CHCH2- A-100 -(CH2)2C(CH3)=CHCH2- A-101 -CH(CH3)CH2-CH=CHCH2- A-102 -(CH2)3CHFCH2- A-10 3 -(ch2)2chf(ch2)2- A-104 -ch2chf(ch2)3- A-105 -(CH2)2CH(CH3)(CH2)2. A-106 -(CH2)20(CH2)2- A-107 -(ch2)2s(ch2)2- A-108 -(CH2)4- A-109 -ch2ch=chch2-

118620.doc -26 - 200800026 No. R1 R2 A-110 'CH(CH3)(CH2)r A-111 -CH2CH(CH3)(CH2)2- A-112 -ch(ch3mch2)2-ch(ch3)- A-113 -CH(CH3MCH2)4- A-114 -CHrCH(CH3)-(CH2)3- A-115 -(ch2)-ch(ch3)-ch2-ch(c^-^ A-116 -ch (ch2ch3mch2)4- A-117 -(CH2)rN(CH3HCH2)2_ A_118 -N=CH-CH=CH- Α-1Γ9 -N=C(CH3)-CH=C(CH3)- A-120 -N =C(CF3)-CH=C(CF3)- A-121 -(CH2)2CH(CH3)(CH2)2- A-122 -(CH2V Among them, especially the following compounds: -5-gas·6 -(2,5-dioxa-4-methylphenyl)-7-(3-methyl-methylpyrazine-1 -yl)-[1,2,4]triazolo-[l,5- a]pyrimidine; -5-methyl-6-(2,5-disorgano-4-methylphenyl)-7-(3-indolylpyrazine-1 -yl)-[1,2 , 4] triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2,5-dioxa-4-methylphenyl)-7-(3-indenylpyrazine洛-1.yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5 - gasyl-6 - ( 2,5 -digas-4 -methylphenyl ) 7 - ( 3 - fluorenyl ° Biha _ 1 -yl) - [1, 2, 4] triazolo-[l,5-a] pyrimidine; -5-chloro-6-(2,5 -difluoro-4-methoxyphenyl)-7-(3-methylindole-1-yl)-[1,2,4]triazolo-[l,5-a] -5-methyl·6-(2,5-dimorph-4-methoxyphenyl)-7-(3-methyl-11-bito-1-yl)-[1,2,4 Triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-methoxyphenyl)-7-(3-methylpyrrolidine- 1-yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methoxyphenyl)- 7-((3-methylpyrrolidine-1-118620.doc -27- 200800026 base)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6 -(2,5-dioxa-4-methylphenyl)-7-(2-indolyl D ratio 11 唆-1-yl)_[1,2,4]triazolo-[l,5 -a]pyrimidine; -5-methyl-6-(2,5·difluoro-4-mercaptophenyl)-7-(2-decylpyrrolidin-1-yl)-[1,2,4 Triazolo-[l,5-a]pyrimidine; ^ -5-methoxy-6-(2,5-difluoro-4-methylphenyl)-7-(2-methylpyrrolidine- 1-(yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-carbyl-6-(2,5-di-gas-4-methylphenyl)- 7 - (2-methyl-pyrrolidine-1 -yl)_ • [1,2,4]triazolo-[l,5-a]pyrimidine; -5 -gas-6 - ( 2,5 -digas-4-methoxyphenyl)· 7 - (2-methyl-11 嘻σ定-1 -yl)~ [1,2,4]triazolo-[l,5-a]pyrimidine ; -5-A -6-(2,5-dioxa-4-methoxyphenyl)-7·(2-methyl 11 ratio leptin-1 ·yl)-[1,2,4]triazolo-[l , 5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-methoxyphenyl)-7-(2-methylpyrrolidin-1-yl)-[1 , 2,4]triazolo-[l,5-a]pyrimidine; - 5-carbyl-6-(2,5-disorder-4-methyllacylphenyl)-7-(2-methyl σ 唆 唆 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -7-(2-methylhexaza σ-pyridin-1-yl)_*[1,2,4]-triazolo[l,5-a]pyrimidine; =-5-mercapto-6 -(2,5-difluoro-4-indolylphenyl)-7-(2-mercaptohexahydropyridin-1-yl)-[1,2,4]-triazolo[l,5-a Pyrimidine; -5-methoxy-6-(2,5-dioxa-4-methylphenyl)-7-(2-methylhexanitrogen 0 to bite-1-yl)-[1,2 , 4]-triazolo[l,5-a]pyrimidine; -5-murine-6-(2,5-disorder-4-methylphenyl)-7-(2-mercapto-6) Ratio °-1 - 118620.doc -28- 200800026 base)-[1,2,4]-two tons and [i,5_a] mouth bite; 5-chloro-6-(2,5-di 14-A Oxyl stupyl): (2-methylhexaazepine than biting small base)-[1,2,4]-dijunz[ΐ35-α]ρ^σ定; 5曱基-6-(2, 5-fluoro-4-methoxy Stupid)_7_(2_decylhexahydroacridine-1-yl)-[1,2,4]-triazolo[l55_a]pyrimidine; 5·decyloxy-6-(2,5-difluoro +methoxyphenyl)-7-(2-methylhexahydroperylation than biting small group Hl,2,4]-tris-[a55-a], pyridine; 5 cyano 6-(2,5-fluoro 4-methoxyphenyl)_7·(2_decylpiperidine-1-yl)-[1,2,4]-triazolo[i,5-a]pyrimidine; -5-chloro-6- (2,5·difluoro-4-methylphenyl)_7_(4-methylhexahydroindolepyridinyl)-[1,2,4]-triazolo[l,5_a]pyrimidine ; -5-mercapto-6-(2,5-difluoro-cardiomethylphenyl)indole_(heart methyl hexaazide mouth bite small base)-[1,2,4]-diindole , -5-methoxy-6_(2,5-difluoro_4.methylphenyl)_7_(indenyl hexahydro ton 唆 1-yl)-[1,2,4]_ triterpene ·, -5-Cyano-6-(2,5-difluoro_4-methylphenyl)_7-(4-methylhexahydrotoxin)-[1,2,4]-dioxin And [1,5-a]^!!定·, _ 5_chloro-6_(2,5-difluoro_4-methoxyphenyl)-7-(4-methylhexahydropyridine-1 - Base)-[1,2,4]-triwax[i,5_a]pyrimidine; _ 5-methyl-6-(2,5-difluoro_4-methoxyphenyl)_7_(4_ Methylhexahydropyridine_1-yl Hl,2,4]-tris-[l55_a]pyrimidine; _ 5-methoxy-6-(2,5 _二就_4·曱oxyphenyl)_7_(4·methylhexahydrotoxin-1-yl)-[1,2,4]_three-salt, %^piperidine; -5-cyanide Base-6-(2,5-difluoro_4-methoxyphenyl)_7_(4-fluorenylhexahydro. Bipyridine _ 118620.doc -29- 200800026 1-yl)-[1,2,4]-triazolopyrimidine; 5H(2'5_H methyl phenyl)_7·(3-methylhexahydro ton bite- 1-Base)-[1,2,4]-Sanjun and [1,5_&]. 5-methyl-6-(2,5-difluoro, 4-review, methyl-based)-7-(3-methylhexahydro. than bite-l-ylyl X1,2,4]-three Azolo[l,5-a]pyrimidine; 5methoxy-6-(2,5-one-failed {methylphenyl) can 7 "3_methylhexaazepine bit _ 1-yl)-[1 , 2,4]-triazolo[l55_a] 啸 ;; 5-cyano-6-(2,5_bisκmethylphenyl)_7_(3-methylhexahydro. 1,2,4]-triazolo[l55_a]pyrimidine; 5-disorder-6-(2,5-difluoro-4-hydroxyphenyl)_7_(3-methylhexahydro 11-pyridine small base )_[1,2,4]-triazolo[i,5_a]pyrimidine; 5-mercapto-6-(2,5_diox_4-methoxyphenyl)-7_(3•fluorenyl) Hexazapine-1-yl)-[1,2,4]-triazolo[i,5-a]pyrimidine; 5methoxy-6-(2,5-difluoro-4-methoxyphenyl) - 7-(3-methylhexahydropyridin-1yl)-[1,2,4]-triazolo-pj-a]pyrimidine; 5-cyano-6-(2,5-difluoro- 4-methoxyphenyl)_7_(3-methylhexahydropyridinium-1-yl)-[1,2,4]-tris-[i,5_a] oxime; 5-chloro-6 -(2,5-difluoromethoxyphenyl)-7-(azepane "-yl)-[1,2,4]dioxin_[1,5-&] continued bite; ·Methyl-6-(2,5-difluoro.4.methoxyphenyl)_7·(nitrogen heterocycle Calcined + yl)-[1,2,4]triazolo-[1,5-a]pyrimidine; 5-methoxy-o-,5-difluoro-4-yloxyphenyl)_7•(aza Cycloheptane-based small base)·Π, 2,4]triazolo-[i,5-a]pyrimidine; 5-cyanopterin-difluoro·4·methoxyphenyl+ 118620.doc -30- 200800026 -[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro-4-indolylphenyl)-7-(nitrogen Heterocyclic heptane-1-yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-mercapto-6-(2,5-difluoro-4-methyl Phenyl)-7-(azepan-1-yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2, 5-difluoro-4-indolylphenyl)-7-(azepan-1-ylHl,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano- 6-(2,5-difluoro-4-mercaptophenyl)-7-(azepan-1-yl)-[1,2,4]triindolo-[l,5-a] Mouth; 5-5-chloro-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclopropylamino Hl,2,4] three-seat-[1,5 - a] mouth σ set; -5-mercapto-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclopropylamino)-[1,2,4] three Zydro-[l,5-a]pyrimidine; -5-decyloxy-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclopropylamino)_ [1, 2,4]three And -[l,5_a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclopropylamino)-[1,2,4 Triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro-4-methylphenyl)-7-(cyclopropylamino)-[1,2 , 4]trim-[1,5-a]^ sigma; -5-methyl-6-(2,5-difluoro-4-mercaptophenyl)-7-(cyclopropylamino )-[1,2,4] triterpenoid-[l,5-a] oxime; -5-methoxy-6-(2,5-difluoro-4-methylphenyl)-7- (cyclopropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-carbyl-6-(2,5-di-gas-4-methylphenyl )-7-(cyclopropylamino)-[1,2,4] 118620.doc -31- 200800026 Triazolo-[l,5-a]pyrimidine; _ 5-chloro-6·(2,5 -difluoro-4-methoxyphenyl)-7-(cyclohexylamino)-[H4]triazolo-[l,5-a]pyrimidine; -5-methyl-6-(2,5 -difluoro-4_methoxyphenylindole 7_(cyclohexylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2 ,5-difluoro-4-methoxyphenyl)-7_ccyclohexylamino)_[1,2,4]triazino-[l,5_a] mouth bite; -5-cyano-6-( 2,5-difluoro-4-methoxyphenyl)_7_(cyclohexylamino)_[1,2,4]triazolo-[l,5-a]pyrimidine; -5 - gas - 6-(2,5-difluoro-4-methylphenyl)-7-(cyclohexylamino)-[ι,2,4]triazolo-[l,5-a]pyrimidine; -5 -Methyl-6·(2,5-difluoro-4-mercaptophenyl)-7-(cyclohexylamino)-[1,2,4]triazino-[1,5-a] 5; -5-methoxy-6-(2,5-difluoro-4-methylphenyl)-7-(cyclohexylamino)-[1,2,4]triazolo-[1, 51]pyrimidine; -5-cyano-6-(2,5-difluoro-4-indolylphenyl)-7-(cyclohexylamino)-[1,2,4]triindole-[l , 5-a] 唆 唆; -5-chloro-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclopentylamino)-[1,2,4] σ sits and -[l,5-a] bites; -5-methyl-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclopentylamino)-[ 1,2,4]trisole-[l,5-a] feeding; -5-methoxy-6...(2,5-difluoro-4-methoxyphenyl)-7-(cyclic Amylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methoxyphenyl) -7-(cyclopentylamino)- •32- 118620.doc 200800026 [1,2,4]trim-[l,5-a], hydrazine; -5-chloro-6-(2,5 -difluoro-4-methylphenyl)-7-(cyclopentylamino H1,2,4]trin-[l,5-ap-bite; -5-methyl-6-(2, 5_difluoro-4-methylphenyl)-7 _(cyclopentylaminotrienol-[l,5-a]pyrimidine; *- 5-methoxy-6-(2,5-difluoro-4-methylphenyl)-7-( Cyclopentylamino)-, [1,2,4]trisole-[l,5-a]«-bite; 5-cyano-6-(2,5-difluoro-4-indolylbenzene -7-(cyclopentylamino)-[1,2,4] ® triazolo-[l,5-a]pyrimidine; -5-gas-6-(2,5-difluoro-4 _Methylphenyl)-7-(N_(2-mercaptopropen-1-yl)-N-ethyl-amino)-[1,2,4]triazolo-[i,5-a] Pyrimidine; 5-methyl-6-(2,5-difluoro-4-methylphenyl)-7-(N-(2-methylpropen-1-yl)-N-ethyl-amino )_[1,2,4]triazolo-[i,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro_4-methylphenylmethylpropene_1β ())-ethyl-amino)-[1,2,4]triazolo-[i,5-a]pyrimidine; _-5-cyano-6-(2,5-difluoro-I methyl Phenylmercaptopropene·buki)-N-ethyl-amino)-[i,2,4]triazolo-[i,5-a]pyrimidine; -5-gas-6-(2,5 _Difluoro_4_methoxyphenyl>7_(N_(2_mercaptopropenyl)-N-ethyl-amino)-[1,2,4]triazolo-[i,5 -a]pyrimidine; ' _ 5_methyl_6·(2,5·difluoro-4-methoxyphenylmethacryloyl)-oxime-ethyl-amino)-[1,2,4 ] Zyrazolo-[i,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-methoxyphenyl)_7_(N_(2-methacryl-1-yl) -1^-ethylamino)-[152,4]triazolo-[1,54]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methoxyphenyl) Xing 7-(Ν兴2-曱-based propylene 118620.doc •33- 200800026 base)-N-ethylamino)-[1,2,4]triazolo-[1,5-&]pyrimidine; -5-Chloro-6 (2,5-difluoro-4-mercaptophenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazole -[l,5-a]pyrimidine; -5-methyl-6-(2,5-ditun-4-methylphenyl)-7-(2,2,2-trifluoroethylamino) )-[1,2,4]triazolo-[l,5-a]pyrimidine; ^ - 5·methoxy-6-(2,5-difluoro_4·methylphenyl)-7- (2,2,2-trifluoroethylamine, yl)-[1,2,4]tris-[l,5-a], decidyl; -5-cyano-6-(2,5- Difluoro-4-methylphenyl)-7-(2,2,2-trifluoroethylamine•yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; 5-Chloro-6-(2,5-difluoro-4-methoxyphenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazole -[l,5-a]pyrimidine; -5-methyl-6-(2,5-difluoro-4-methoxyphenyl)-7-(2,2,2-dioxaethylamino )-[1,2,4]triazolo-[l,5- a]pyrimidine; -5-methoxy-6-(2,5-di1-4-methoxyphenyl)-7-(2,2,2-tri-Iethylamino)-[1, 2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5-dioxo-4-oxooxyphenyl)-7-(2,2,2 -trifluoroethylamine)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methyl- 6·(2,5-difluoro^-4-曱Oxyphenyl)-7-((1,2,2-trimethylpropan-, 1-yl)amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; , -5-Cyano-6-(2,5-difluoro-4-yloxyphenyl)-7-((1,2,2-tridecylprop-1-yl)amino)-[ 1,2,4]triazolo-[l,5-a]pyrimidine; ,-5-methoxy-6-(2,5-difluoro-4-methoxyphenyl)-7-(( 1,2,2-trimethylpropan-1-yl)amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5 -difluoro-4-methylphenyl)-7-((1,2,2-trimethylprop-1-yl) 118620.doc -34- 200800026 Amino-Hl,2,4]triazolo-[ l,5-a]pyrimidine; -5·methyl_6-(2,5-difluoro-4-mercaptophenyl)-7-((l,2,2-trimethylpropan-1·yl) Amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methylphenyl)-7 -((1,2,2-trimethylprop-1-yl) Amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5_曱lactyl-6-(2,5-dioxa-4-methylphenyl)-7 -((1,2,2-dimethylpropan-1-yl)amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-gas-6- (2,5-Difluoro-4-methylphenyl)-7-((1,2,2-trimethylprop-1-yl)•amino)_[1,2,4]triazolo- [l,5-a]pyrimidine; -5-gas-6-(2,5-difluoro-4-methylphenyl)-7-(1,2-dimethylpropylamino)-[1 , 2,4] triple spitting-[l,5-a] sneezing; -5-methyl-6_(2,5-difluoro-4-methylphenyl)-7-(1,2-di Mercaptopropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-ylphenyl) )_7-(1,2-dimethylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5 - gas group _6-(2,5 - Dimethyl-4-methylphenyl)-7·(1,2-dimethylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5 - Gas-6-(2,5-dioxa-4-methoxyphenyl)-7-(1,2-dimercaptopropylamine)-[1,2,4]triazolo-[ l,5-a]pyrimidine; -5-methyl-6-(2,5-difluoro-4-methoxyphenyl)-7-(1,2-dimethylpropylamino H1, 2,4]triazolo-[l,5-a]pyrimidine -5-methoxy-6 - ( 2,5 · di- gas - 4 -methoxyphenyl)-7 - (1,2-dimercaptopropylamino)-[1,2,4 Triazolo-[l,5-a]pyrimidine; -5-murine-6-(2,5-diox-4-methoxyphenyl)-7-(1,2-dimethylpropane Base amine 118620.doc -35- 200800026 base)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro-4-methyl Phenyl)-7-(1-mercaptopropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-mercapto-6-(2,5 -difluoro-4-methylphenyl)_7-(1-methylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; '-5-methoxy- 6-(2,5-Difluoro-4-mercaptophenyl)-7-(1-mercaptopropylamino)-[1,2,4]triazolo-[l,5-a] Pyrimidine; -5-cyano-6-(2,5-difluoro-4-indolylphenyl)-7-(1-mercaptopropylamino)-•[1,2,4]triazole -[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro-4-methoxyphenyl)-7-(1-mercaptopropylamino)-[1, 2,4]triazolo-[l,5-a]pyrimidine; -5-methyl-6-(2,5-disorder-4-methyllacylphenyl)-7-(1-mercaptopropyl Amino))-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy-6.(2,5-difluoro-4-methoxyphenyl) -7-(1- Propylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; _-5-cyano-6-(2,5-difluoro-4-methoxybenzene -7-(1-mercaptopropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-gas-6-(2,5-digas 4-methylphenyl)-7-(2-methylpropylamino)_ • [1,2,4]triazolo-[l,5-a]pyrimidine; --5-methyl- 6 - (2,5-difluoro^-4-methylphenyl)-7-(2-methylpropylamino)·[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy·6-(2,5-dioxa-4-methylphenyl)-7-(2-methylpropylamino)-[1,2,4]triindole-[ l,5-a]carcinoma; -5-murine- 6-(2,5-dioxa-4-methylphenyl)-7-(2-methylpropylamino)- 118620.doc • 36- 200800026 [1,2,4]二嗤弁-[1,5_&] shouting 17; 5-chloro-6-(2,5-difluoro-4-methoxyphenyl)-7-( 2-methylpropylamino)-[1,2,4]dipyridinium_[1,5_&] shouting; 5-methyl-6-(2,5-difluoro-4-methoxy Phenyl)-7_(2_mercaptopropylamino)· [152,4]dipyridinium_[1,5_3]carcinoma; 5-methoxy-6-(2,5-difluoro-4 -methoxyphenyl)_7_(2-methylpropylamino)-[1,2,4]triazolo-[i,5-a]pyrimidine; 5- Cyano-6-(2,5-difluoro-4-methoxyphenyl)_7_(2-methylpropylamino)_[1,2,4]tris-[i,5-a Pyrimidine; 5-chloro-6-(2,5-difluoro-4-methylphenyl)-7-(2,2,3,3,4,4,4-heptafluorobutylamino) -[1,2,4]triazolo-[i,5-a]pyrimidine; 5-methyl winter (2,5-difluoro-4-methylphenylfluorobutylamino)-[1, 2,4]三峻和_[i,5-a] feeding; 5-methoxy-6_(2,5-difluoro_4_methylphenylheptafluorobutyl-amino)-[1 , 2,4]triazolo-[i,5-a]pyrimidine; 5-cyano-6-(2,5-difluoro-4-methylphenyl)_7_(2,253,3,4,4,4 _heptafluorobutylamino)-[1,2,4]triazolopyrimidine; 5-chlorobutyl (2,5-difluoro |methoxyphenyl)_7_(2,2,3,3,4 , 4,4_heptafluorobutyl-amino Hl,2,4]triazolopyrimidine; 5-methyl-6-(2,5-difluoro_4_methoxyphenyl)7_(2,2 ,3,3,4,4,4_heptabutyl-amino)-[1,2,4]triazolo-[15_a]-nosine; 5 methoxy·6-(2,5·2 Fluoromethoxyphenyl)_7·(2,2,3,3,4,4,4-heptabutyl-amino)-[1,2,4]triterpene.[1,5-&amp ;]Nursing; 5-cyano winter (2,5-difluoro | methoxyphenyl to resemble seven-hearted heptafluoro 118620.doc -37- 200800026 butyl-amino group)-[1,2,4 ] Triazolo[na]pyrimidine; and agriculturally acceptable salts thereof. The compounds of the invention can be obtained by different routes. Preferably, they are suitably substituted with a phenylmalonate of the formula 5-a-female oxadiazole and a hydrazine of the formula (wherein R is a calcinyl group, preferably a Cl-C6_alkyl group, a particularly preferred system). Methyl or ethyl) is prepared according to the synthetic route reaction shown in Figure 1. Reaction Figure 1:

In the reaction scheme 1, R1, R2, L1, and L2 are as defined above. Hal Halogens, especially chlorine and R alkyl groups, are preferred. alkyl. The reaction of the aminotriazole π with the substituted phenylmalonic acid S is usually between go. (between 3 to 250 ° C, preferably from 120 ° C to 180 ° C in the absence of solvent or in the presence of a base in an inert organic solvent [see European Patent No. A 770 615] or in acetic acid In the presence of a bee member known from Adv. Het. Chem. 57, p. 81 ff. 118620. doc-38-200800026 (I" 3) Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons (for example, Benzene, o-, m- and p-biphenyl), halogenated hydrocarbons, ethers, nitriles, ketones, alcohols, and methylpyrrolidone, dimethyl sulfoxide, dimethyl decyl amide and dimethyl Acetamide. More preferably, the reaction is carried out in the absence of a solvent or in chlorobenzene, xylene, dimethylhydrazine or N-methylpyrrolidone. It is also possible to use a mixture of such solvents. In summary, suitable base inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, metal and soil metal oxides, metal and soil metal hydrides, metal amines, alkali metals and alkaline earth metal carbonates Salt and metal hydrogencarbonate, organometallic compounds, in particular alkali metal alkylates, alkyl halides And an alkali metal and an alkaline earth metal alkoxide and a dimethoxy group; or an organic base, for example, a tertiary amine such as tridecylamine, triethylamine, diisopropylethylamine, tributylamine And _methylhexahydropyridine, N-methylmorpholine, pyridine, substituted pyridine (for example: collidine, dimercapto π ratio iutidine and 4 dimethylamino group Bite) and bicyclic amines. Particularly preferred is the use of tertiary amines such as diisopropylethylamine, tributylamine, N-mercaptomorpholine or N-methylhexahydropyridine. It is usually used in a catalytic amount; however, it can also be used in molar amounts, in excess or, if appropriate, as a solvent. The starting materials are usually reacted with each other in molar excess. Excess base and malonate m based on diterpenes are used. The phenylmalonate of formula III is preferably catalyzed by Cu(I) by appropriately substituted bromobenzene and dialkyl propionate [Refer to chemistry Letters (1981), pp. 118620.doc-39-200800026 pp. 367-370; European Patent No. A i(4) 2m]. Obtained by Formula IV and V The composition is novel and also forms part of the subject matter of the present application. Subsequent to the standard method of organic chemistry (for example, the conditions known from w〇_A 94/2〇5〇1) • Conversion to a di-azolopyrimidine of the formula v wherein Hal is a halogen atom, preferably a bromine atom or a chlorine atom, particularly preferably a gas atom. The _chemical agent [HAL] used is preferably a gasifying agent or a A brominating agent (e.g., phosphonium bromide or phosphonium chloride), if appropriate, is used in the presence of a solvent. The reaction is usually carried out under conditions of from 0. 0 to 125. 〇 [Shenfang Renzhou Patent No. 7 7 〇 615] was implemented. The dihalotriazolopyrimidine of formula v is then further reacted with an amine of formula VI wherein R and R are as defined in formula 1 to provide a 5-halo-triazolopyrimidine of formula VII. Compound VII corresponds to a ruthenium wherein χ = halogen. It is also advantageous for the vehicle to react with v and VI at a temperature of from 7 〇C to 3 5 c: preferably from an inert solvent (e.g., an ether such as dioxa In the presence of a fluorinated or especially tetrahydrofuran; a hydrocarbon such as methylene chloride or an aromatic hydrocarbon such as toluene (refer to W〇-A 98/46608). Preferably, a base (e.g., a tertiary amine such as triethylamine; ^4\\\ machine test, such as potassium carbonate) is used; an excess of the amine of formula VI can also be used as the base. The compound wherein X is a cyano group, a CKCV alkoxy group or a Cl_C2_haloalkoxy group can be obtained in a preferred manner by reacting a compound of the formula I wherein X is a halogen, preferably a chlorine group, with the compound Μ_χ, (Formula VIII). . Depending on the group X' to be introduced, the compound VIII is an inorganic cyanide, alkoxide or a halogen 118620.doc 200800026 a burned oxide. The reaction is preferably carried out in the presence of an inert, gamma | 丨月r raw/troreal. The cation enthalpy in formula VIII is not critical; ammonium, tetraalkylammonium or metal or soil metal salts are generally preferred for practical reasons. l(x=halogen) + M-Xf~^^ VIII '(χ = χ,) The reaction temperature is usually from 0 °C to UOt:, preferably from 1 (rCi4(rc [see factory "^61*〇( ^〇1.(:1^111., Vol. 12, pp. 861-863 (1975)].

Suitable solvents include ethers (e.g., dioxane, diethyl ether, and preferably tetrahydrofuran), sulphuric acid (e.g., monomethyl) and aromatic hydrocarbons (e.g., toluene). The compound of the formula I wherein the oxime system is substituted can be obtained in a preferred manner by the following synthesis route:

In the reaction scheme 2, 'R1, R, L1, and L2 are as defined above. The Hai is a halogen, especially a gas 'R-based alkyl group, preferably a Ci_C6_alkyl group. Starting with 颜| vinegar iiia, '5-alkyl-7-ylamino-6-phenyl triterpene was obtained and iva was taken. In the formulas Hia and IVa, 'X1 is a Ci-C4·Hyun group or a Ci-CV halogenated group. Acetic acid vinegar obtained by the use of Keqi Yi (Ilia which resigned 5 118620.doc -41 - 200800026 methyl-7-hydroxy_6_phenyltriazolopyrimidine [Ref. Chem. pharm Bull., 9, 8〇1 (1961)] The starting compound ma is preferably prepared under the conditions described in European Patent No. a 10 02 788. The resulting 5-alkyl-7-hydroxy-6-phenyl group The triazolopyrimidine iva is reacted with a halogenating agent [HAL] under the conditions described above to obtain a 7-halogenated tris-hydrazine and a pyridine. Preferably, a chlorinating agent or a brominating agent is used, for example. Phosphonium bromide, disc brewing chlorine, sulfoxide chlorine, sulfinium bromide or sulfonium chloride. The reaction can be carried out in pure form or in the presence of a solvent. The conventional reaction temperature is 〇〇c to l5〇〇c or preferably. From 80 ° C to 25 ° C.

The reaction of Va with amine VI is carried out under conditions as further described above. The compounds of the formulae IVa and Va are relatively novel and also form part of the subject matter of this application. Or 'wherein (: 1-(4-alkyl compound of formula I can also be prepared from compound VII wherein X is especially gaseous and malonate of formula IX. In formula IX, X" is hydrogen or CrCy alkyl and R are alkyl. These reactions give compounds of formula X and are decarboxylated to give compound I [see U.S. Patent No. 5,994,360].

Δ / Η + X in the reaction diagram 3

Ri, R2, L1 I (X=C 1 -C焼) L2 is as defined above. R is an alkyl group, preferably a Ci-CV alkyl group. Malonate (IX) is available from the reference [J· Am·Chem· 118620.doc -42- 200800026

Soc. 64 (1942) ?714 · τ ^ ^ , , J· 0rg· Chem. 39 (1974), 2172; Helv·

Chim. Acta 61 (1 〇 7r\ i c/cci, ), 565] is known or can be prepared according to the cited references. The hydrolysis of vinegar is carried out under normal use conditions. It may be advantageous to carry out alkaline or acidic hydrolysis of the compound X by looking at different structural elements. Under the conditions of hydrolysis, it may have been completely or partially slowed down into a deficient usually at 20. (: to 180. (::, preferably from 5 〇. (: to 12 〇. (: at a temperature in an inert solvent (if appropriate) in the presence of a single acid. , sulfuric acid, phosphoric acid, formic acid, acetic acid, p-benzoic acid. Suitable solvents are water, aliphatic hydrocarbons (eg, pentane, hexane, cyclohexane, and petroleum ether), aromatic hydrocarbons (eg, hydrazine). Benzene, o-... and p-diphenyl, halogenated fumes (eg, dichlorodecane, gas and benzene), ethers (eg, diethyl ether, diisopropyl ether, third butyl ketone, Dioxane, anisole and tetrahydrofuran), nitriles (for example, acetonitrile and propionitrile), ketones (for example, acetone, methyl ethyl ketone, diethyl ketone and third butyl ketone), alcohol (e.g., decyl alcohol, ethanol, n-propanol, isopropanol, n-butanol, and third-butanol) and dimethyl sulfite, dimethyl decylamine and dimercaptoacetamide; Preferably, the reaction is carried out in hydrochloric acid or acetic acid. A mixture of the solvents may also be used. The compound of formula I wherein the oxime is 4* alkyl may also be obtained by making the formula γη 5_halo The oxazolopyrimidine is obtained by reacting with an organometallic reagent of the formula XI. In one embodiment of the process, the reaction is carried out using a transition metal catalyst such as Ni catalyst or Pd catalyst. 118620.doc -43- 200800026 Ι (χ=(ν(:4-alkyl) νιι + My(-xu)y χι In Formula XI 'The lanthanide is a metal ion with a valence of Υ, such as Β, Ζη or Sn and X" is a CkCU-alkane The reaction can be carried out, for example, by a method similar to the following: J. Chem. Soc. Perkin Trans. 1, 1187 (1994), ibid. 1, 2345 (1996); WO-A 99/41255; AUst. J. Chem., Vol. 43, 733 (1990); J. Org Chem, Vol. 43, 358 (1978); J,

Chem. Soc. Chem. Commun. 866 (1979); Tetrahedron Lett., vol. 34, 8267 (1993); ibid. Vol. 33, 413 (1992). The reaction mixture is treated in a conventional manner, for example by mixing with water, phase separation and, if appropriate, chromatography. Certain intermediates and final products are obtained in the form of a colorless or slightly brown viscous oil which is purified under reduced pressure and at moderately elevated temperatures or free of volatile components. . If the intermediates and final products are known as solids, they can also be purified by recrystallization or cooking. If an individual compound cannot be obtained by the above route, it can be obtained by derivatization of another compound I. If the synthesis produces a mixture of isomers, it is usually not necessary to carry out the separation, since in some cases the individual isomers are known to be produced during the treatment of hydrazine or during application (eg 'light, acid' Or the test occurs after use, for example, the 4^ k 44 transition can also occur in the harmful fungi to be controlled. The compound of formula I is suitable for use as a fungicide. The pathogen bacterium K is known for its efficacy from the following classes and sputum: ascomycetes (four), as well as semi-sense sputum, scutellaria (7) saki _^), oomycetes 118620.doc -44- 200800026 (〇(10);^如) and Basidiomycetes (5(10)·山·(10)), and especially the Agrobacterium-like fungi. Certain of the compounds of this invention are effective in a systemic manner and are useful as plant fungicides, seed dressing fungicides and soil fungicides for plant protection. It is controlling a variety of cultivated plants, such as wheat, rye, doctor oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugar cane: vines, fruits and ornamental plants, and vegetables (such as cucumbers, beans, tomatoes) , potatoes and cucurbits, and a large number of fungi on the seeds of these plants are particularly important. It is especially suitable for controlling the following plant diseases: - vegetables, rapeseed, sugar beets and fruits and the genus of Fusarium oxysporum (10) r(4) on rice (eg bottom rot (Potato yo/anz·) or tobacco on potato and tomato Alternaria (children; - sweet-smelling and silky genus on plants;

- Bifidobacteria and Deraxia on corn, grain, rice and lawn (Drech/eraJ) (eg, Helminthosporium ssp. in barley on barley (D) (four), wheat leaf spot blight on wheat (D) triHci_ repentis)); - powdery mildew on the grass (^S/wmer/α powdery mildew); - Botrytis cinerea C7wrea on strawberries, vegetables, flowers and vines (gray m〇 Id)); - disease on the disease / aeiwcae); - corn, soybean, rice and sugar beetle on the genus Cereo (ore genus (such as sugar beet on the beet (C. Z^z_cw / <2)); 118620.doc -45- 200800026 - genus of Helminthosporium (CW/z/iok/z^) on corn, sorghum, rice (eg Helminthosporium on grain, rice) Cochliobolus miyabeanus Y ·, - Soybean, cotton and other plants on the genus Cocos (Co/Zeioir / cz / mj genus (such as various plants on the genus Fusarium oxysporum (C · ; - on corn) Exserohilum ·, - Phytophthora bisporus dc/zoracearz/m on gourd and Sphaerotheca fuliginea ·,

- Fusarium and Verticillium on various plants (eg Verticillium dahliae (K da / ζ / ία illusion (such as F. graminearum on wheat) \ - The top of the scorpion Capsular bacterium (Gaewm (four) less gramzWd, · grain and gibberella of rice (G/6Z^re//a) genus (eg Gibberella fujikuroiY on rice), - grain on rice Dyeing complex; - Phytophthora spp. on corn and rice (eg KH graminicola) ·, - Snowy blight on grain (Mic/zra and cr/2/wm mva/J / - sputum, fragrant coke and genus of the genus Coccidia on the peanuts (M. gramk/co/Dian, banana on the banana, black leaf spot pathogen (M· /X/z'es/ s)); Phytophthora serrata j^c/^r/n'zz·) on soybean and Pseudomonas aeruginosa; - Soybean, geranium and vines (T/ Ramc^pdd genus (Portugal 118620.doc -46- 200800026 vine grape downy mildew (Ρ· WHco/W, 曰 上 上 he helianthii); - Phytophthora infestans on potatoes and tomatoes) - Grape downy mildew on vines (Τ/α says opara Wii Co/aj ; - White sclerotium / ewcoir / c / za on apple trees; - Herpotrichoides on the scorpion) » - Helminthosporium on hops and cucurbits (eg cucumber downy mildew on cucumber (P.; - grain, corn and asparagus on the rust fungus (P. triticina on wheat) (P. triticina) counterfeit, window (P, striformis), 1 Phytophthora sinensis (household;; - nucleocapsid bacteria on cereals (TyrMop/^rW genus; - rice porphyra on rice, rice porphyry (Coriz'ezVm, rice lychee emblem (*Sar6^) /aiiz'wm, rice leaf sheath spoilage, rice leaf black powder (five oryzae) / - lawn and grain on rice grains (/^rz_cw/arz.grbea); - lawn, rice, corn, cotton, rapeseed, Pythium on sunflowers, beets, vegetables and other plants; - cotton, rice, horseshoe, turf, corn, rapeseed, potatoes, beets, vegetables and other plants of the genus Rhizoctonia f Bacteria (and·;, 118620.doc -47- 200800026 - Sclerotinia on rapeseed, sunflower and other plants (Sc/eroi/WaJ genus (eg rapeseed) Nuclear disease (& / - wheat on the shell of the needle and the genus Stagonospora nodorum; - the vine on the powdery mildew, also known as: Uncinula necator); - corn and lawn *Seiospaer/a ; - Sphacelotheca reiiinia on corn ·,

- TTz/eva/io/^zj genus on soybeans and cotton / - genus sphaeroides (77//...α) of the grain, · - genus Ustilago on cereals and beets; and - apple And the genus of black spot (FeWwr/α) on the pear (black spot disease) (for example, apple on t-ticket, I disease { V, inaequalis, 〇 formula I compound is also suitable for materials (for example, wood, paper, paint) Control of harmful fungi in terms of protection of liquids, fibers or fabrics and protection of stored products. In the protection of wood, special attention should be paid to the following harmful fungi: Ascomycetes, such as the genus SPP.) ), Aureobasidium pullulans, scorpion I (Sclerophoma s), Chaetomium spp., Humicioa spp., spp., Hairy mildew ( 7Wc/2wrw spp.); Basidiomycetes, for example, C. genus (Ccm/op/zora spp.), Clostridium (Corio/ws spp.) 'Glycyrrhiza (G/α(9)p/^/ / said spp.), Pleurotus spp·), Pleurotus sp. (P/ewroiw spp.), 茯苓 Ρ〇 (Ρ〇η·α Spp.), Long Jie 118620.doc -48 - 200800026 genus (Serpw/a spp· ) Genus (rjromyca spp.); deuteromycetes, such as Aspergillus spp.), genus Bacillus (C/adoiS^or/wm spp.), Penicillium (/Γαζ_ϋζ7//ι^ spp .), Trichoderma (TWc/zWerma spp.), Alternaria (j/iernaria spp.), Paecilos genus (Paecz7omj; ca spp·); and zygomycetes, such as Mucor (Μι /cor spp.); and in terms of protective materials, note the following yeast: Caec/Ma spp. and Saccharomyces cerev/sae. The compound of formula I is effective by using a fungicidal effective amount. The active compound treats the fungus or the plant, seed, material or soil to be protected from fungal attack. The application can be carried out before or after the application of the fungus infection of the material, plant or seed. Such fungicidal compositions typically comprise between about 1% and 95% by weight, preferably between 0.5% and 90% by weight of active compound. When used for plant protection, depending on the type of desired effect, the applied amount is between 0. 01 kg of active compound per hectare and 2 kg of active compound per hectare. In seed treatment, the amount of active compound is usually required to be from 1 g/100 kg seed to 1000 g/100 kg seed, preferably 5 g/100 kg seed to 100 g/100 kg seed. When used for the protection of materials or stored products, the amount of active compound applied will depend on the type of application area and the desired effect. The amount usually applied in the protection of the material is, for example, 0.001 g of active compound per cubic meter of treated material to 2 kg of active compound per cubic meter of treated material, preferably 0.005 g of live 118620.doc -49-200800026 sex compound/cubic The treated material is 丨 kg of active compound per cubic meter of treated material. The compounds of formula I may exist in various crystalline modified forms having different biological activities. It may also form part of the subject matter of the invention. The compounds of formula I can be converted into conventional formulations, for example, solutions, emulsions, suspensions, powders, powders, pastes and granules, depending on the particular intended use; in each case, it is ensured that the compounds of the invention Finely and evenly distributed. These formulations may be prepared in a known manner, for example, by blending the active compound with a solvent and/or a carrier, if necessary, an emulsifier and a dispersing agent may be used. Solvents/auxiliaries for this purpose are mainly: - water, aromatic solvents (eg, solvesso products, xylene), rocky soils (for example, mineral oil fractions), alcohols (eg 'methanol, butanol, pentanol, section Alcohol) ketones (eg ' ketone ketone, r _butyrolactone pyrrolidine: ethylene glycol ethylene glycol (tetra)), glycols, fatty acid dimethyl amines, fatty acids and fatty acid vinegars. Mixtures, _上' can also use solvent-loading agents, such as crushed natural minerals, territories, clay, talc and crushed synthetic minerals (such as ancient gossip 0. ^ Λ . .矽 皿 ) ' ' 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 礼 例如 例如 例如 例如 例如 例如 例如 例如 例如 例如 例如 例如 例如 例如 例如 例如And disperse (4) 'such as lignin sulfite waste liquid and methyl cellulose. = Suitable surfactant for lignin continuous acid test gold and ammonium salt, naphthalenesulfonic acid, benzene-based soil test metal butyl naphthoquinone Acid 'alkylaryl 118620.doc -50- 200800026

In addition to the acid salts, alkyl sulfates, alkyl sulfonates, aliphatic alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, the suitable surfactants used may also be sulfonated. a condensate of naphthalene and naphthalene derivatives with methyl, a condensate of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethyl octyl phenyl hydrazine, ethoxylated isooctyl phenol, octyl phenol, hydrazine Benzophenone, alkyl phenyl polyglycol ether, tributyl phenyl polyglycol ether, tristearyl phenyl polyglycol ether, alkyl aryl polyether alcohol, alcohol and aliphatic alcohol Ethylene oxide condensate, ethoxylated castor oil, polyoxyethylene ethyl ether, ethoxylated polyoxypropylene, lauryl polyethylene glycol ether acetal, sorbitol ester, Lignin sulfite waste liquid and methyl cellulose. High-boiling mineral oil fractions suitable for the preparation of materials which can be directly sprayed with solutions, emulsions, pastes or oil dispersions, such as kerosene or diesel, in addition to, for example, coal tar and oils derived from plants or animals, aliphatic Hydrocarbons, cyclic hydrocarbons and aromatic hydrocarbons (such as toluene, xylene, paraffin, tetralin, alkyl = naphthalene or its derivatives), methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, iso Falconone, a highly polar solvent (eg dimethyl sulfoxide, decyl pyrrolidone and water). The earth powder, i.e., the material for spraying and the applicable product, can be prepared by mixing or simultaneously grinding the active material with a solid carrier. " Granules (e.g., coated granules, impregnated granules, and granules) can be prepared by blending the active compound with a solid carrier. Examples of solid carriers are mineral soils such as tannins, citrates, talc, kaolin, attaclay, S-grey, lime, white, red basalt, loess, clay, dolomite, and stone eve. Algae, sulfur, magnesium sulfate, 118620.doc • 51- 200800026 Magnesium oxide, ground synthetic minerals; fertilizers, for example, ammonium sulfate, phosphonium, ammonium nitrate, urea and plant products, for example, cereals Powder, bark coarse powder, wood flour and nut shell meal, cellulose powder and other solid carriers. In general, the formulation comprises from about 5% by weight to about 95% by weight, more preferably from 0.1% by weight to 90% by weight of hydrazine. The purity of the active compound used is between 90% and 100%, preferably between 95% and 1% (according to NMR spectrum). The following are examples of formulations: 1 - Products diluted with water: A Water-soluble concentrate (SL, LS) 10 parts by weight of the active compound of the formula I are dissolved in 9 parts by weight of water or a water-soluble solvent. As an alternative, wetting agents or other auxiliary agents may be added. The active compound can be dissolved by dilution with water. According to this method, a formulation having an active compound content of 10% by weight is obtained. B Dispersible Concentrate (DC) 20 parts by weight of the active compound of the formula I are dissolved in 7 parts by weight of cyclohexanone, and 10 parts by weight of a dispersing agent (for example polyvinylpyrrolidone) are added. After dilution with water, a dispersion is formed. The active compound content is 2% by weight. C emulsifiable concentrate (EC) 15 parts by weight of the active compound of the formula I are dissolved in 75 parts by weight of xylene, calcium dodecylbenzene sulfonate and ethoxylated castor oil are added (each added 5 parts by weight). After dilution with water, an emulsion is formed. This formulation has an active compound content of i 5 wt%. D Emulsion (EW, EO, ES) 25 parts by weight of the active compound of the formula I are dissolved in 35 parts by weight of dimethyl 118620.doc -52-200800026 benzene, adding calcium dodecylbenzene sulfonate and ethoxylate Basecast castor oil (5 parts by weight each). This mixture was introduced into 30 parts by weight of water by means of an emulsifying machine (for example, uitraturrax) to prepare a homogeneous emulsion. After dilution with water, an emulsion is formed. This formulation has an active compound content of 25% by weight. E Suspension (SC, OD, FS) In a carrying: ball mill, 20 parts by weight of the active compound powder β of the formula I is crushed, while adding 10 parts by weight of the dispersant and wetting agent and 70 parts by weight Water or an organic solvent to form a suspension of the fine active compound. After dilution with water, a stable suspension of the active compound is formed. The active compound content of the formulation was 20% by weight. F dispersible in water particles and water-soluble granules (WG, SG) 50 parts by weight of the active compound of the formula I are finely ground, while adding 5 parts by weight of dispersant and wetting agent, and by means of technical equipment ( For example, an extruder, a spray tower, a fluidized bed) are used to form particles or water-soluble particles that are dispersible in water. After dilution with water, a stable dispersion or solution of the active compound is formed. I The active compound content of this formulation is 50% by weight. G can be dispersed in water powder and water-soluble powder (WP, SP, SS, WS) 75 parts by weight of the active compound of formula I is ground in a rotor_stator grinder while adding 25 parts by weight of dispersant, Wetting agent and silicone. After dilution with water, a stable dispersion or solution of the active compound is formed. The active compound content of the formulation is 75% by weight. ΗGel formulation in a ball mill, grinding 20 parts by weight of the active compound of formula I, 1 part by weight of dispersant, 1 part by weight of gelling agent and 7 parts by weight of H8620.doc-53 - 200800026 Water or organic solvent to form a fine suspension. After dilution with water, a stable suspension having an active compound content of 20% by weight is obtained. 2. Products which can be administered without dilution I Powder (DP, DS) 5 parts by weight of the active compound of the formula I are finely ground and thoroughly mixed with 95 parts by weight of the fine kaolin. Thereby, a powdery product having a content of 5% by weight of the active compound is formed. J granules (GR, FG, GG, MG) _ Finely ground 0.5 parts by weight of the active compound of the formula I together with 99.5 parts by weight of the carrier. Current methods are extrusion, spray drying or fluidized beds. Thereby, a granule having a content of 5% by weight of the active compound which can be administered without dilution can be formed. K ULV solution (UL)

10 parts by weight of the active compound of the formula I are dissolved in 90 parts by weight of an organic solvent such as diphenylbenzene. Thereby, a product which can be administered without dilution can be formed with an active compound content of i0% by weight. For seed treatment, water-soluble concentrate (LS), suspension (FS), powdered (DS), dispersible in water and water-soluble powder (ws, ss), chyle (ES), emulsifiable Concentrate (EC) and gel formulations. These formulations T are administered to the seed in a form that is not dilute, released or preferably diluted. Administration can be carried out prior to sowing. Spraying, spreading or casting or using the active compounds prepared therefrom may be carried out by spraying, spraying, etc. in the form of their formulations, in the original state, for example, directly sprayable solutions, powders, suspensions or fractions. Forms used 118620.doc -54- 200800026 for the purpose of evacuation; it is intended to be as fine as possible in the form of oil liquid dispersions, pastes, spreadable products, substances or granules. The form of use depends entirely on the desire to ensure that the active compound of the invention can be in a finely distributed state in each case. The 3 water use form can be prepared by adding an emulsion concentrate, a paste or a methane (wettable powder, oil dispersion) by adding water. For the agent, paste or oil dispersion, it can be used as a wetting agent, glue (4), dispersant:

Emulsifying hydrazine to make these substances or their solutions in oil or solvent homogenized in water. However, it is also possible to prepare active substances, wetting agents, adhesives, dispersants or emulsifiers and, if appropriate, solvents or oils. The concentrates are composed and the concentrates are suitable for dilution with water. The concentration of the active compound in the ready-to-use preparation can vary over a relatively wide range. In general, these concentrations are preferably between 0.0001% and 1% between 0.0001% and 1%. These active compounds can also be used with great success in ultra low volume processes (u Lv), it is possible to apply formulations having more than 95% by weight of active compound or even to apply active compounds without additives. Various oils, wetting agents, adjuvants, herbicides, fungicides, other insecticides, or bactericides may be added to the active compound, and may be added (tank mix) as appropriate, as appropriate. These agents may be mixed with the composition of the present invention in a weight ratio of from 1:10 to 1 :1, preferably in an amount of from 0 to 1. The appropriate adjuvant is especially modified by organic modification. Polyoxyalkylene such as Break Thru S 2408; alcohol alkoxylates, such as Atplus 245®, 118620.doc -55- 200800026

Atplus MBA 1303®, Plurafac LF 300® and Lutensol ON 30®; EO/PO block polymers such as Pluronic RPE 2035® and Genapol B®; alcohol ethoxylates such as Lutensol XP 80®; and dioctylsulfonate Sodium sulphate, such as Leophen RA®.

The compositions of the present invention may also be used in combination with other active compounds in the form of fungicides, for example, in combination with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. By mixing the compound (I) or a composition comprising the same with one or more other active compounds (especially fungicides), it is possible in many cases to broaden the spectrum of activity or prevent the occurrence of drug resistance. In many cases, synergies can be achieved. The following list of fungicides that can be used in combination with the compounds of the present invention is intended to clarify possible combinations, but not to limit them: Staples urinary mouth azoxystrobin, dimoxystrobin, alkene Esstroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifluoro Trifloxystrobin, oresastrobin, (2·chloro-5-[1-(3·decylbenzyloxyimino)ethyl]benzyl)carbazinate, (2- Methyl-5-[l-(6-decylpyridin-2-ylmethoxyimino)ethyl]benzyl)amino decanoate, 2-(o-(2,5-dimethyl) -phenoxyarylene)phenyl)-3-decyloxy decyl decyl ester; decylamine-formaldehyde aniline · benalaxyl, wheat rustling 118620.doc -56 - 200800026 (benodanil), boscalid, carboxin, mepronil, fenfuram, fenhexami Amid), flitolanil, furametpyr, metalaxyl, ofurace, oxadixyl, oxycarboxin, D Penthiopyrad, thifluzamide, tiadinil, Ν·(4'·bromobiphenyl-2-yl)-4-difluoromethyl-2-mercaptothiazole -5-decylamine, N-(4'-trifluoromethylbiphenyl-2-yl)-4-difluoroindol-2-methylthiazole-5-carboxamide, Ν-(4· -Chloro-3'-fluorobiphenyl-2-yl)-4-difluoromethyl-2-mercaptothiazol-5-nonylamine, N-(3',f-digas-4-fluorine Phenyl-2-yl)-3-difluoromethyl·1-methylpyrazole-4-carboxamide, N-(2-cyanophenyl)-3,4-dioxathiazole-5- Methionine; - retinoic acid morphine · dimethomorph, flumorph; - benzamide · flumetover, fluopicolide Benzoylamine), zoxamide; - other methotrexate: carpropamid, diclocymet, mandipropamid, N-(2- (4-[3-(4-chlorophenyl)propane-2 - fast ]]-3-methoxyphenyl)ethyl)-2-carcinogen xanthylamino-3-methyl-butanamine, N-(2-(4-[3-(4-phenylphenyl) )prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-ethyl sulphate yellow amine 3-methylbutylimamine; sputum-triterpenoid: white Bitertanol, bromuconazole, 118620.doc -57- 200800026

Cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, 护石夕(flusilazole), fluquinconazole, flutriafol, hexaconazole imibenconazole, ipconazole, metconazole, maicyclobutyl Myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, three Triadimenol, triadimefon, triticonazole; - miso: cyazofamid, imazalil, pefurazoate, poker (prochloraz), triflumizole; - benzo miso list: benomyl, carbendazim, fuberidazole, thiabendazole; - other : 衣沙布山(ethaboxam ), etridiazole, hymexazole; nitrogen heterocyclic compound-deuterium bite: fluazinam, pyrifenox, 3-[5-(4- Gas phenyl)-2,3-dimercaptoisoxazolin-3-yl]-pyridine; - σ-type bite: B, sulfonate (cypridin), cyprodinil, feeding knee (ferimzone), fenarimol, 118620.doc -58 - 200800026 mepanipyrim, nuarimol, pyrimethanil; - maiden: Safun (triforine); _ σ pylon: fludioxonil, fenpiclonil; - morphine: aldimorph, dodemorph, fenfluk ( Fenpropimorph), tridemorph;

- Diweicarbammines: iprodione, procymidone, vinclozolin; others: S-methyl aspirin (acibenzolar-S-methyl), carbendazim (anilazine) ), captan, captafol, dazomet, diclomezine, fenoxanil, folpet, fenpropidin , famoxadone, fenamidone, octhilinone, probenazole, proquinazid, pyroquilon, quinoxen (quinoxyfen), tricyclazole, 5-gas-7-(4-methylhexahydro 0-bit-1-yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]三嗤[1,54]Nutrition, 2_Butoxy-6-Edan_3_propyl·Effects 4 -酉,Ν,Ν-dimethyl_3- (3-Mo, -6-fluoro-2_fluorenyl 0-derived bee-1-yellow base)-[1,2,4]-tris-saltamine; amino phthalate and dithio Urethane-dithiocarbamates: ferbam, mancozeb, maneb, free (metiram), Meitan 118620.doc -59 - 200800026 (metam), methyl zinc, propineb, thiram, zineb, ziram; - urethane Class: diethofencarb, flubenthiavalicarb, iprovalicarb, ppanmocaine 1: 〇0&111〇〇&1:13), 3- (4-Chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutanylamino)propionic acid methyl ester, N-(l-(l-(4-cyanophenyl)) 4-fluorophenyl ester of ethionyl)butan-2-yl)amino decanoate; other fungicides - venom: dodine, iminoctadine, dioctylated octylamine Guazatine); - antibiotics: kasugamycin, polyoxins, streptomycin, validamycin A; - organometallic compounds: triphenyltin salt; Sulfur-containing heterocyclic compounds · isoprothiolane, dithianon; - organic filling compounds: edifenphos, fosetyl, fosetyl-aliiminum , propyl shesson (iprobe Nfos), pyrazophos, tolclofos-methyl, sub-acid and its salts; - organochlorine compounds: thiophanate-methyl, chlorothalonil, Dichlofluanid, tolylfluanid, flusulfamide, hydrazine, hexachlorobenzene, pencycuron, quintozene; Binapacryl, white powder gram 118620.doc -60- 200800026 (dinocap), dinobuton; - inorganic active compound: Bordeaux mixture, copper acetate, copper hydroxide, copper oxide, Basic copper sulphate, sulphur; - others: spiroxamime, cyflufenamid, cymoxanil, metrafenone 实施 [embodiment] Synthesis Example The procedures described in the examples are used to suitably modify the starting compounds to prepare other compounds of formula I. The compounds and physical data prepared in this manner are collectively listed in the table below. Example 1: 5-Gas-6-(2,5-Difluoro-4-methoxyphenyl)-7-(N-ethyl-N-(2-methyl)-2-propene-l-yl Amino)-;ι,2,4-triazolo[l,5a]pyrimidine 3 g (9 mmol) 5,7-dichloromethane in 30 ml of dioxane at room temperature -6-(2,5-di-1-4-methoxyphenyl)-1,2,4-tris-[1,5&] guanidine (similar to WO 94/20501 by making 2-amine Base-1,2,4-triazole and diethyl 2_(2,5-difluoro-4-methoxyphenyl)malonate were prepared by reversed and subsequently densified), 0.9 g (9.1 house) Mole) N-ethyl-(2-methyl)-lean propylamine and 0.9 g (9 mmol) of triethylamine were stirred overnight. The reaction mixture was then mixed with dilute hydrochloric acid and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over 1 mL of EtOAc and evaporated. The residue was purified by preparative MPLC (mobile phase: acetonitrile/water 70:30) on celite RP-18. From this, 2.4 g (68% of theory y colorless solid title compound (Hybrid 129 〇C) 〇118620.doc -61 - 200800026 tNMMCDClu in ppm): 8·4 (s5 1H); 7.0 (dd5 1H) 6.85 (dd5 1H); 4.9 (s5 1H); 4.8 (s5), 4·〇(s, 3H), 3·75 (m, 1H); 3.5 (m, 3H); 1.6 (s, 3H) ; l〇5 (t,3H) Example 2: 5_曱oxy_6_(2,5-difluoro.4_methoxyphenyl)_7_(n_ethyl_N_(2-methyl)anthracene Propyl-amino)], 2,4-triazole and pyrimidine • 5 g (1.27 mmol) of 5_chloro-6-(2,5-difluoromethoxy) at room temperature Phenyl)-7-(N-ethyl·N_(2-methyl)allylamino)-1,2,4-triazolo[1, called acridinium (from Example 1} and 〇·3 The mixture was stirred overnight in 10 mL of MeOH. EtOAc (EtOAc m. Purification of the preparative MPLC (mobile phase: acetonitrile/water 70:30) on EtOAc EtOAc (EtOAc: EtOAc) 164<t). h-NMRKDCUd in ppm): φ 8 25 (S' 1H), 6.95 (dd, 1H); 6·8 (dd, out); 4.9 (s, 1H); 4.8 (s , 1H); 4.0 (S, 3H); 3.95 (S) 3H); 3.7 (m, 1H); 3.45 (m, 3H); 1.6 (s? 3H); 1.1 (t3 3H) Example 3 · 5_Cyanide -6-(2,5-difluoro_4-methoxyphenyl)·7_(Ν_ethyl-N_ , (2-fluorenyl)allylamino)-l,2,4-tri Oxazolo[l,5a]pyrimidine ^ at room temperature T, will be stored in 10 ml of B guess, 0 5 g (127 mmol) 5_ chloro 6-(2,5-fluoro-4-methoxybenzene Base)_7_(Ν·ethyl-yi^·methyl)allylamino)-1,2,4-tris-[1,5a] mouth bite (from example 1) Α〇85 g (3) Millimol) Tetraethylammonium cyanide was stirred overnight. The reaction mixture was then diluted with 118620.doc-62-200800026 diluted hydrochloric acid and extracted three times with dichloromethane. The combined organic phases were dried over sulphuric acid and concentrated under reduced pressure. The residue was purified by silica gel RP_18 (preparative MPLC mobile phase·acetonitrile/water 70:30). The title compound was obtained as a yellow oil (yield: 62%). h-NMRCCDClhS in ppm): 8.55 (s, ih); 7·05 (dd, 1H); 6.9 (dd, 1H); 4.95 (s, 1H); 4.85 * (s, 1H); 3.85 (m5 1H 3.6 (m5 3H); 1.6 (s5 3H); 1.1 (t, 3H) Example 4: 5-methyl-6·(2,5-difluoro-4-methoxyphenyl)-7-( N-ethyl-N· • (2_mercapto)allylamino)-l,2,4-triazolo[l,5a]pyrimidine 4·1· 5 -methylpropane -6-(2,5-difluoro-4-methoxyphenyl)_7_(team ethyl-indole-(2-methyl)allylamino)-indole, 2,4-triazolo[ l,5a] 1 g (2.5 mmol) of 5-chloro-6-(2,5-difluoro-4-methoxybens)-7-(N-B) in 20 ml of acetonitrile --N-(2-methyl) propyl propyl)) 1,2,4-triazolo[l,5a]pyrimidine (from example 丨) and ι·2 g (7.5 mM) Sodium dimethylmalonate was heated under reflux for 3 hours. Then another sodium dimethyl dimethyl malonate was added and the ester was further heated (HPLC: partial conversion). The mixture was then cooled to room temperature and the precipitated yellow solid was transferred with celite. The yellow solid obtained in this way was mechanically separated from the diatomaceous earth and mixed with a mixture of dichloromethane and dilute hydrochloric acid. The phases were then separated and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over magnesium sulfate and concentrated. The residue was purified by preparative MPLC (mobile phase·acetonitrile/water 60:40) on silica gel RP-18. Thus, 2 g (16% of theory) of a flavin oil-like title compound was obtained. 118620.doc -63- 200800026 ^-NMR (CDC135 δ in ppm): 8.4 (s,1H); 6·85 (m,2H); 4·9 (s,1H); 4.85 (s,1H); 4·7 (s3 1H); 4.0 (s5 3H); 3.8 (s, 3H); 3.75 (m5 1H); 3.7 (s3 3H); 3.5 (m, 3H); 1.6 (s, 3H); 1.05 (t ,3H) 4·2· 5-methyl-6-(2,5-difluoro_4-methoxyphenyl)_7_(N_ethyl_N-(2-methyl) propyl propylamino )-l, 2, 4_ 三嗤[1,5&]. 2 g (0.4 mmol) of dimethylpropanediyl-6-(2,5-difluoro-4-methoxyphenyl)_7_(Ν-ethyl) in 10 ml of methanol Methyl)allylamino)-1,2,4-triazolo[i,5a]pyrimidine (Example 4A) and 0.13 g of a 50% by weight sodium hydroxide solution were heated under reflux for 8 hours. The reaction mixture was then diluted with water, acidified with dilute hydrochloric acid and extracted thrice with dichloromethane. The combined organic phases were dried over magnesium sulfate and concentrated. Preparative MpLC was carried out on silica gel RP_18: the residue was purified. This gave 35 mg (23% of theory) of title compound as a yellow oil. W-NMI^CDClhS in ppm)·· 8.35 (s5 1H); 6.95 (dd, 1H); 6.85 (dd5 1H); 4.9 (s, 1H); 4.8 (s, 1H); 4.0 (s, 3H) ; 3·75 (m,1H); 3 55 (4) 1H); 3.45 (d5 1H); 3.35 (m5 iH); 2.35 (s5 3H); 1.6 (s5 3H); 1·〇5 (t,3H) The compounds listed in l are prepared in a similar manner: 118620.doc -64- 200800026

Example R1 R2 X L1 L2 Melting point PC]1), iH-NMR [ppm], HPLC/MS [M/H+2] 2 -CH2C (=CH2) (CH3) C2H5 Cl 0CH3 F Melting point 126-129 2 -ch2c(=ch2)(ch3) C2H5 OCH3 OCH3 F Melting point 162-164 3 _ch2c(=ch2)(ch3) C2H5 -CN〇OCH3 F iH-NMR See above 4 -CH2C(=CH2)(CH3) C2H5 ch3 OCH3 F iH-NMR see above 5 cyclopentyl H Cl OCH3 F melting point 73 6 -CH2CH(CH3)CH2CH2CH2-Cl OCH3 F melting point 124-127 7 -CH2CH2CH2CH2CH2CH2-Cl 0CH3 F melting point 140-143 8 cyclohexyl H Cl OCH3 F yellow oily 9 cyclopropyl H Cl OCH3 F melting point 183-184 10 -CH2CH(CH3)CH3 H G1 OCH3 F melting point 116 11 -ch2ch(ch3)ch2ch2-Cl OCH3 F melting point 77-97 12 -ch(ch3 Ch2ch2ch2-Cl 0CH3 F HPLC/MS 3.449/380 13a) -ch(ch3)ch(ch3)2 H Cl OCH3 F HPLC/MS 3.548 / 382 14b) •ch(ch3)ch(ch3)2 H Cl OCH3 F HPLC/MS 3.547/382 15b) -ch(ch3)c(ch3)3H Cl OCH3F HPLC/MS 3.746/396 16 -ch(ch3)ch2ch2ch2ch2-Cl 0CH3 F Melting point 79-100 17a) -ch(ch3) c(ch3)3 H Cl OGH3 F HPLC/MS 3.750 / 396 18 -CH2CH2CH(CH3)CH2CHr Cl OCH3 F mp 82-90 19a) -CH(CH3)C2H5 H Cl OCH3 F HPLC/MS 3.357 / 368 2 0 -CH2CH2CH(CH3)CH2CH2-Cl ch3 F Melting point 176-178 21 -CH2C(=CH2)(CH3) C2H5 Cl ch3 F Melting point 141-143 22b) ch(ch3)c(ch3)3 H Cl ch3 F 146- 148 23b) _ch(ch3)ch(ch3)2 H Cl ch3 F 123-125 24 ch2cf2cf2cf3 H Cl och3 F 95-105 25c) ch(ch3)c(ch3)3 H Cl OCH3 F 131-134 26 CH2CF3 H Cl OCH3 F HPLC/MS 3.206/394 27 GH2CF3 H Cl ch3 F 154-156 1) Melting point 2) Combined HPLC-mass spectrometry: HPLC column: RP-18 column (Chromoiith Speed ROD from Merck KGaA, Germany); Mobile phase: acetonitrile + 0.1% trifluoroacetic acid (TFA) / water + 〇 · 1% 118620.doc -65- 200800026 TFA 'with a gradient from 5:95 to 95:5, 5 minutes at 4 〇t. MS.·Quaternary electrospray ionization, 8〇v (positive mode) a) Enantiomeric mixture b) R isomer c) S isomer application example Greenhouse experiment·· Prepare these active compounds separately or It is co-prepared to include a stock solution of milligrams of active compound using acetone and/or DMSO with an emulsifier

A mixture of Uruperol® EL (wetting agent with emulsification and dispersion, based on ethoxylated alkyl phenol) was made up to 10 ml with a solvent/emulsifier volume ratio of 99/1. Subsequently, this mixture was made into 1 ml of water with water. This stock solution was diluted with the above solvent/emulsifier/water mixture to the following active compound concentration. Microtest: The active compounds were separately formulated into stock solutions in dimethyl sulfoxide at a concentration of 10,000 ppm. Application Example 1 - Activity against gray mold on bell pepper leaves caused by Botrytis cinerea at 1 day of prophylactic application: Spraying with an aqueous suspension having the following active compound concentration has completely grown 2 to The leaf of the three leaf cultivars "Neusiedler Ideal Elite" leaves to the diarrhea point. The next day, the treated plants were inoculated with a spore suspension containing i.7 x 1 〇6 spores/ml of Botrytis cinerea in a 2% aqueous solution of bimalt (biomalt). The test plants were then placed in a dark soil domestication room at 118620.doc -66 - 200800026 22-24 ° C and high atmospheric humidity. After 5 days, the degree of fungal infection on the leaves was visually observed in %. In this test, 63 ppm of plants treated with the compound of Example 18 showed no infection, while 63 ppm 5-chloro-7-(4-methylhexahydroindole-bu)-6-(2-fluoro) was used. 30% of plants treated with _4_methoxyphenyl)-1,2,4-triazolo-[l,5-a]pyrimidine were infected. 100% of untreated plants are infected. In this test, plants treated with 63 ppm of compounds from Examples 1, 3, 4, 11, 12, 13, 14, 15, 16, 17, 18, 19, 22, 23, 26 and 27 showed no infection. Or infection is less than 5%, and 90% of untreated plants are infected. Application Example 2 _ Resistance to rice blast pathogen rice porphyra in a microtiter test: The stock solution was pipetted onto a microtiter plate (MTP) and diluted with a malt-based aqueous fungal nutrient medium. To the concentration of the active compound. The aqueous spore suspension of Pear is then added. The plates were placed in a water vapor saturation chamber at 18 c degrees. On the 7th day after inoculation, an absorbance measurement was used to measure 2 ΜΤΡβ at 405 nm. The measured parameters were compared with the growth of the control variant containing no active compound and the blank value without fungi and without the active compound. Relative growth (in %) of pathogenic bacteria in the active compound alone. In this sputum 'has been treated with 125 PPm of compound from Example 18: the sample shows no pathogen growth' and has been used with 125Ppm5_chloro·7_(4_methyl hexa-6 ratio -6 base)-6-(2 -Fluoro-4-carbenium Α ίί* Α, 1 1 paper 4 4 Τ 基本 base) _1,2,4-triazolo-[l55_a] The pyrimidine-treated sample showed 39% relative growth. 118620.doc -67 - 200800026 Application Example 3 - Resistance to Phytophthora infestans in a microtiter test The solution was pipetted onto a microtiter plate (Μτρ) and used for water based on pea juice The fungal nutrient medium dilutes it to the active compound concentration. An aqueous zoospore suspension of the disease-causing epidemic is then added. The plates were placed in a water vapor saturation chamber at a temperature of 18 °C. On the 7th day after inoculation, an MTp at 4 〇 5 nm was measured using an absorbance luminosity. The relative growth (in %) of the pathogens in the individual active compounds was determined by comparing the measured parameters to the growth of the control variant without the active compound and the blank value without fungi and without the active compound. In this test, 31 ppm of the sample treated with the compound of Example 15 showed 5% pathogen growth, while 3 1 ppm 5 - gas _7-((1 (R)-methyl-2,2- The sample treated with mercaptopropyl)amino)-6-(2-fluoro-4-methoxyphenyl;) 4,2,4-triazolo-[l,5-a]pyrimidine showed 72% Relative growth. Application Example 4 - Resistance to early blight pathogens Alternaria Solani in a microtiter test (Alteso)

The stock solution was pipetted onto a microtiter plate (MTP) and diluted to the active compound concentration using a malt-based aqueous fungal nutrient medium. An aqueous spore suspension of Alternaria Solani was subsequently added. The plates were placed in a water vapor saturation chamber at a temperature of one. At 7 days after the inoculation, an MTP at 4 〇 5 nm was measured using an absorbance luminosity. The relative growth (in %) of the pathogens in the individual active compounds was determined by comparing the measured parameters to the growth of the control variant without the active compound and the blank value without the fungus and without the active compound. I 118620.doc -68- 200800026 In this case, a sample treated with 0. 125 ppm of the compound from Example 25 showed 41% relative growth, while 0.125 ppm 5-chloro-7- (2, 2,2-Trifluoro-1(8)-mercaptoethyl)amino-6-(2,5-difluoro-4-yloxyphenyl)_1,2,4-diazolopyrimidine treatment The sample showed a relative growth of 1%. Application Example 5 - Resistance to the therapeutic activity of wheat brown rust caused by puccinia rec〇n (jita) with spore suspension of leaf recorded disease (Puccinia reticulata) The cultivar "Kanzler" was planted in potted wheat seedling leaves. The plant pots were then placed in a chamber with a lower air humidity (90 to 95%) for 24 hours. During this time, the spores germinate and the germ tubes penetrate the leaves. In the next day, the infected plants are sprayed to the diarrhea point using the above active compound solution having the following active compound concentrations. After the spray liquid has dried, the test plants are tested at a temperature between 20 C and 22 The culture was carried out for 7 days in a greenhouse at between ° C and relative humidity of 65% to 7 %. The extent of development of rust fungi on the leaves was then determined. Of the plants treated with 250 PPm of the compound from Example 21 showed less than 5% infection, while 25 〇ppm 5_chloro_7_(ice (2_methyl)allyl·Ν-ethylamino fluoride) _4_mercaptophenyltriazolo-[l,5-a]pyrimidine-treated plants showed 1%% infection. 100% of untreated plants were infected. Application Example 6 - Resistance by bottom rot Activity of tomato early blight caused by pathogens Spray the leaves of potted plants to the liquid point with an aqueous suspension having the following concentration of active compound. The next day, use in 2% bi〇malt solution 118620.doc -69- 200800026 and an aqueous suspension of spores of bottom rot fungi with a density of 孢·17χ106 spores/ml infects the leaves. Subsequently, the plants are placed in a water vapor saturation chamber at a temperature between 20 ° C and 22 ° C. After 5 days, the condition of the untreated but infected control plants has progressed to the extent that the infection score (in %) can be visually observed. In this test, 63 ppm has been used from Examples 1, 2, and 3. , 4, 11, 12, 13, 14, 15, 16, 16, 17, 18, 19, 21, 22, 23, 24, 26 and 27 Compound treated plants showed no infection or infection less than 1%, while _ 90% of untreated plants were infected. Less than 10% of plants treated with 250 ppm of Example 20 were infected.

118620.doc -70-

Claims (1)

200800026 X. Applying for a patent garden: 1. A triazole of formula I. Use of dense destructive fungi σ定 and its agriculturally acceptable salts for controlling plants (I) wherein the substituents are defined as follows: Is a C alkyl group, a C1_C8-haloalkyl group, a c3_c8-cycloalkyl group, a C3-(V _.-cyclo-alkyl group, a c2-c8-alkenyl group, a c2-c8- _alkenyl group, a C3_C6_cyclo-dense group , C3_C6-iS cycloalkenyl-alkenyl, CVC8-alkynyl, CyCV haloalkynyl or phenyl, naphthyl or a hetero atom containing 1, 2, 3 or 4 from a group consisting of ruthenium, N and S a 5- or 6-membered heterocyclic ring, R-hydrogen or one of the groups described for R 1 wherein i, 2, 3 or 4 of the hydrogen atoms in the above substituent R 1 and/or 2 may be the same or different Group Ra substitution: Ra cyano, nitro, hydroxy, Ci-CV alkyl, cvc6_haloalkyl, CVCV alkylcarbonyl, C3-C6-cycloalkyl, CV c6-alkoxy, CVCV halo-alkane Oxyl, Ci-CV alkoxycarbonyl, CkCV alkylthio, Cr-CV alkylamine, bis-(VC 6 -alkylamino, C2-C8 - dilute, C2-C8*-halogenated , C 3 -C 8 -cycloalkyl, C 2 -C 6 -oxy, C 3 -C 6 -halooxy, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 - Fast oxygen 118620.doc, C3-CV haloalkynyloxy, c3_c6_cycloalkoxy, c3-6 cycloalkenyloxy, oxy-Cl-C3-alkylalkoxy, phenyl, naphthyl, one containing 1 to 4 a 5 to 10 membered saturated heterocyclic ring of a hetero atom of a group consisting of free 〇, N&s, or a portion of the aliphatic, cycloaliphatic or aromatic group may be partially or partially halogenated and/or There are 1 to 3 groups Rb: Rb is a cyano group, a nitro group, a hydroxyl group, a decyl group, an amine group, a carboxyl group, an aminocarbonyl group, an aminothiocarbonyl group, an alkyl group, a halogenated alkyl group, an alkenyl group, an alkenyloxy group, Alkynyloxy, alkoxy, _alkoxy, alkylthio, alkylamino, dialkylamino, decyl, alkylcarbonyl, alkylsulfonyl, alkyl thiodecyl, Alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, wherein the alkyl group of the group comprises 1 Up to 6 carbon atoms and the alkenyl or alkynyl groups mentioned in the groups contain 2 to 8 carbon atoms; and/or 1 to 3 of the following groups: cycloalkyl, cycloalkoxy, hetero a cyclic group, a heterocyclic oxy group, wherein the ring system contains 3 to 1 ring members; aryl, aryloxy, arylthio, arylalkoxy, aryl-Ci-CV alkyl, heteroaryl Base, heteroaryloxy, heteroaryl Wherein the aryl groups preferably contain from 6 to 10 ring members containing 5 200800026 or 6 mourning members, wherein the ring systems may be partially or fully halogenated or may be alkylated Or i-substituted alkyl; Or R1 and R2 may be combined with the nitrogen atom to which they are attached - a 5 or 6 membered heterocyclic ring via a gas linkage and further containing I, 2 or 3 = heteroatoms from the group consisting of 0, N and S a ring member and which may carry 1, 2, 3 or 4 substituents from the group consisting of: _, Ci-cv alkyl, deuterated alkyl, C2-C6, yl, c2-c6-halogen Alkenyl, Ci-cv alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, (external (V-alkyl and oxy-C1- C3 - an extended alkyl group; L1 is an alkyl group or (VCV alkoxy, L2 is a fluorine, chlorine or CVCV alkyl group, X-line, cyano, CVC4-alkyl, cvc4-haloalkyl , cr C4 alkoxy or (^_(: 4-haloalkoxy; Wherein when R2 is hydrogen and X is halogen, R1 is not a group of the formula CH(CF3)-(CrC4 alkyl). 2. The use of the claimed item, wherein the halogen in the formula I is halogen. 3_ The use of claim 1, wherein X is a cyano group, a Cl_C4 alkyl group, a Ci-CV alkoxy group or a Ci_Cr haloalkoxy group. 4. The use of any of the preceding claims, wherein L2 in formula I is fluoro. 5. The use according to any of the preceding claims, wherein L1 is a methoxy group. 6. If requested! The use of any one of 4, wherein Li is a fluorenyl group in Formula 1. The use of any of the above claims, wherein 118620.doc 200800026 R in formula I is C4-c8-alkyl, c3-c8-cycloalkyl, c3-C8- _cycloalkyl, C3- CV alkenyl, c3_C8-i alkenyl, c3_c6df alkenyl, halocyclodecyl, C^C8-alkynyl, CVC8-haloalkynyl or phenyl, naphthyl or one containing 1, 2, 3 or 4 a 5- or 6-membered heterocyclic ring derived from a hetero atom consisting of ο, N, and S; and R is a gas - C1-C3-alkyl or C1-C3-halogenated, wherein the group R 1, 2, 3 or 4 hydrogen atoms may be substituted as claimed in claim 1. The use according to any one of claims 1 to 6, wherein in the summer, R is a C 2 - C 8 -haloalkyl group and the R system is a C1-C3 -alkyl group or a Ci-C3-_alkyl group. . The use of any one of claims 1 to 6, wherein the group nr1r2 constitutes a 5 or 6 membered heterocyclic ring via a nitrogen linkage and further comprises 1, 2 or 3 when appropriate A hetero atom derived from a group consisting of ruthenium, N and S as a ring member and which may carry 1, 2, 3 or 4 substituents from the group consisting of halogen, Ci-C6-alkyl, C丨-C6-haloalkyl, c2-C6-alkenyl, C2-C6-haloalkenyl, Ci-CV alkoxy, CVCV haloalkoxy, C3-C6-alkenyloxy, (:3-(:6) - _ alkenyloxy, (external ycVCV alkylene and oxyalkyloxy. 10. The use of any one of claims 1 to 1, wherein in formula I R2 is hydrogen, methyl or ethyl and R1 is C4-C8-alkyl, C4-C8-alkenyl, (VCV-alkylene or C3-C:6-cycloalkyl, wherein such groups may, when appropriate, carry one of the following groups: Ra Is a cyano group, a nitro group, a hydroxy group, a CrC6-alkylcarbonyl group, a c3-c6-118620.doc 200800026 a cycloalkyl group, a c^cv alkoxy group, a CVC6-alkoxycarbonyl group, a Cr c6-alkylthio group, (^ -(: 6-alkylamino, di-Ci-CV alkylamino, dilute, C2-C6-thinyl, C3-C6-fastoxy, C3-c6-cycloalkoxy, c3-C6-cycloalkenyloxy, oxy-Cr Cy-alkoxy, phenyl, naphthyl, one containing from 1 to 4 groups consisting of ruthenium, N and s a 5 to 10 membered saturated heterocyclic ring of a hetero atom, wherein the ring group itself may be partially or fully ylated or may have 1 to 3 groups Rb. 11. Each of claims 1 to 6 The use thereof, wherein the group ^^...2 is a group of the formula A: (8) H3C and ijJR2 # wherein C2-C6-alkyl, Cl_c4•alkoxymethyl or earth R is as defined above and # indicates the connection of the triazolopyrimidine skeleton. /, bite strength A. The use of any of the claims, wherein C is 3HCl oxime, the R2 is chlorine and the lanthanide CV , cvc4-alkoxy or a substituted oxy group. The soil, Cl- species is selected from the group consisting of: ♦ and n, 5_a] 0 ^ and the salt thereof can be used for controlling plant destructive fungi ·· I, _ 5ϋ(2,5-difluoro+methylphenyl(6), 2 sense trisyl)_amine Hl,2,4;^ sit and 唆; soil 118620.doc 200800026 -5-曱 base -6-(2,5-difluoro-4-mercaptophenyl)-7-((2,2,2-trifluoro-methylethyl)-amino -[1,2,4]triazolo-[i,5-a]pyrimidine; -5 - gasyl-6-(2,5--fluoro-4-methylphenyl)_7-((2,2 , 2-三|^1_曱芙ethyl)-amino)-[1,2,4]diindole-[i,5-a] continued sigma; _ 5_decyloxy-6-( 2,5-difluoro-4·decylphenyl)_7_((2,2,2-trifluoro-4-indenyl)-amino)_[1,2,4]tris-[i] , 5_a] biting; _ 5-mercapto-6-(2,5-difluoro-4-methoxyphenyl)_7_((2,2,2-trifluoromethylethyl)-amino) -[1,2,4] 三嗤和_[i,5_a] bites; _ 5_cyano-6-(2,5-difluoro_4_decyloxyphenyl)7_((2, 2,2_trifluoro-p-methylethyl)-amino)-[1,2,4]triazolo-[i,5_a]pyrimidine; -5-methoxy-6-(2,5-di Fluor-4-methoxyphenyl)_7-((2,2,2jH methyl-ethyl)amino)-[1,2,4]triazolo-[^4]pyrimidine. A fungicidal composition comprising a solid or liquid carrier and at least one of the above formulae and/or an agriculturally acceptable salt thereof. A seed comprising at least one compound of the formula I as claimed in any one of the claims and/or an agriculturally acceptable salt thereof. 16. The species used to control plant pathogenicity. A method of treating cockroaches, plants, and earthworms by treating the fungi with a compound of the formula 1 of the formula 1 or by protecting them from fungi. Or seed. 17·—The third type of formula I sits and squats 118620.doc 200800026 wherein the substituents Ri, R2, x, LjL2 are defined, and in the JL, the R2# gas', the kisses 1 to 12, the Nakata R system, and the X-based halogen, Rl is not (Cl) -C4-alkyl) group, (3)- and compound 5·chloro-6-(2,5·difluoro-4·methoxyphenyl)methylpropanyl)amino)MW] (( 外. Li,) aJ in pyridine and its salt except 18· as in the formula 17) triazolopyrimidine, methoxy. Where L2 is fluorine, then L1 is not 19·If you ask for the item 17! The three saliva will bite, and the sputum will burn. 2〇. A group selected from the group consisting of: (1) (4) 啶 · · · _ 5-chloro-6_(2,5_difluoro_"ylphenyl)_7_((2,2,2-three gas · 曱 乙基 ethyl)-amino)-[1,2,4]triazolo-[^4]pyrimidine; soil _ 5-methyl_6_(2,5-difluoro_4.methylphenyl) _7_((2,2 义三气小methylethyl)-amino)-[1,2,4]triazolo-[υι]pyrimidine; soil _ 5-cyano_6_(2,5_2 Appearance _4_methylphenyl)_7_((ethylamino)-π,2,π-salt(tetra);^methyl_ 5-methyl-6_(2,5_digas·cardiomethoxybenzene )--7-((2,2 义三气小methylethyl)-amino)-[1,2,4]triazolo-[i,5-a]pyrimidine; _ 5-cyano _6_( 2,5_二气_4•methoxyphenyl)_7_((2,2,2_trisoctamethylethyl)-amino)-[1,2,4]triazolo-[i , 5_a] pyrimidine; and agriculturally acceptable salts thereof. 21. A triazolo[^4]pyrimidine selected from the group consisting of: _ gas-6-(2,5-digas-4-A Phenyl) _7_(3_methylpyrrolidine small group) [1,2,4] ternary-[l,5_a] biting; 118620.doc -7 - 200800026 _ 5·methyl-6-( 2,5-difluoro-4-mercaptophenyl)-7-(3-indolylpyrrolidine-l-yl Hl,2, 4] Triazolo-[l,5-a]pyrimidine; -5-methoxy-6 -( 2,5 ·dioxa-4-indolylphenyl)-7 - (3-methyl σpiro _ 1-based Hl,2,4]triazolo-[l,5-a]pyrimidine; -5-azino-6-(2,5-diqi_4-methylphenyl)-7 -(3-methyl ° piroxime-1-_yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; , -5-gas-6-(2,5_ Difluoro-4-decyloxyphenyl)-7-(3-methylpyrrolidin-1-yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; _ - 5- Methyl-6-(2,5-difluoro-4-methoxyphenyl)-7-(3-methylpyrrolidin-1-yl)-[1,2,4]triazolo-[l , 5-a]pyrimidine; -5 -decyloxy-6-(2,5-difluoro-4-decyloxyphenyl)-7-(3-methylpyridin-1-yl)- [1,2,4]triazolo-[l,5-a]pyrimidine; -5-carbyl-6-(2,5-di-n--4-methoxyphenyl)-7-(3 - fluorenyl. piroxicam _ 1-yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5 - gas - 6- (2,5 - digas-4 -nonylphenyl)-7-(2-methyl-pyrrolidine-1-yl)_^[1,2,4]triazolo-[l,5-a]pyrimidine; -5-fluorenyl -6-(2,5-dioxa-4-methylphenyl)-7-(2_fluorenyl σ 唆 唆-1 _ yl)-[1,2,4]triazolo-[l, 5-a]pyrimidine; ' -5-decyloxy-6-(2,5-difluoro-4-methylphenyl)-7-(2-methylpyrrolidin-1-yl)-[1,2,4] Zydro-[l,5-a]pyrimidine; -5-murine-6-(2,5-di-rho- 4-mercaptophenyl)-7-(2-methyl σ-Bisto bite-1 _ -[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro-4-methoxyphenyl)-7-( 2-methylpyrrolidin-1-yl)-[1,2;4]triazolo-[l,5-a]pyrimidine; 118620.doc -8- 200800026 -5-mercapto-6-(2, 5. Difluoro-4-indolylphenyl)-7-(2-methylpyrrolidin-1_yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; 5_decyloxy-6-(2,5-difluoro-4.nonyloxyphenyl)-7-(2-decylpyrrolidin-1-yl)·[1,2,4]triazole -[l,5-a]pyrimidine; -5 -muryl-6-(2,5-dioxa-4-methoxyphenyl)-7-(2-indolyl σpirin. _ 1-yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro-4-indolylphenyl)- 7-(2-methylhexahydropyridin-1-yl)-[1,2,4]-triazolo[l,5-a]pyrimidine; -5-methyl-6 _(2,5 - two Gas-4-methylphenyl)-7-(2-methylhexaazin-1-yl)-[1,2,4]-triazolo[l,5-a]pyrimidine; -5_ Methoxy-6-(2,5-dioxa-4-methylphenyl)-7-(2-methylhexanitropyridin-1-yl)-[1,2,4]-triazole [l,5-a]pyrimidine; -5-murine-6-(2,5·difluoro_4-methylphenyl)-7-(2-mercaptohexahydro-sigma ratio _ 1-yl) -[1,2,4]_triazolo[l,5-a]pyrimidine; -5-gas-6-(2,5-diox-4-methoxyphenyl)-7-(2- Methyl hexanitrogen 11 ratio biting _ 1-yl)-[1,2,4]_triazolo[l,5-a]pyrimidine; -5-mercapto-6-(2,5·2 mouse-4 -methyllacyl phenyl)-7-(2-methylhexazone 0-pyridyl-1-yl)-[1,2,4]-triazolo[l,5-a]pyrimidine; -5-曱Oxy-6-(2,5-difluoro-4-decyloxyphenyl)-7-(2-mercaptohexahydroacridin-1-yl)-[1,2,4]-triazole [l,5-a]pyrimidine; -5-murine-6-(2,5-difluoro 4-4-methoxyphenyl)-7-(2-methylhexahydro 11-pyridin-1- Base)-[1,2,4]-triazolo[l,5-a]pyrimidine啶; -5 - lact-6-(2,5-disorder-4-mercaptophenyl)-7-(4-methylhexa-sigma 唆-1-yl)-[1,2,4] - Triazolo[l,5-a]pyrimidine; 118620.doc -9- 200800026 -5-methyl-6-(2,5-difluoro-4-indolylphenyl)-7-(4-A Hexahydropyridin-1_yl)-[1,2,4]-triazolo[l,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-indole Phenyl)-7-(4-methylhexahydroacridin-1-yl)-[1,2,4]-triazolo[l,5-a]pyrimidine; -5 - gas group - 6_( 2,5-dioxa-4-methylphenyl)-7-(4-methylhexanitroindole-1-yl)-[1,2,4]-triazolo[l,5-a] Pyrimidine; 5-5-chloro-6-(2,5-difluoro-4-methoxyphenyl)-7-(4-mercaptohexahydroacridin-1-yl)-[1,2,4] -Triazolo[l,5-a]pyrimidine; -5-methyl-6-(2,5-difluoro-4-ylmethoxyphenyl)-7-(4-mercaptohexahydroacridine -1-yl Hl,2,4]-triazolo[l,5-a]pyrimidine; -5-methoxy-6-(2,5-diox-4-methoxyphenyl)-7 -(4-mercaptohexanitro 13-pyridin-1-yl)-[1,2,4]-triazolo[l,5-a]pyrimidine; -5 - gasyl-6-(2,5 - Difluoro-4-decyloxyphenyl)-7-(4-mercaptohexa-frostyryl-1-yl)-[1,2,4]-triazolo[l,5-a]pyrimidine; -5·气- 6- (2,5 - Di-[4-methylphenyl)-7-(3-indolylhexanitro). Specific bite-1_yl)-[1,2,4]-triazolo[l,5-a]pyrimidin-5-mercapto-6-(2,5-disorder-4-methylphenyl)- 7-(3-indolyl-6-nine 0 to 17-decyl-1-yl)-[1,2,4]_triazolo[l,5-a]pyrimidine; -5-methyllacyl-6-(2 ,5-dioxa-4-methylphenyl)-7-(3-indolylhexanitro-11-pyridin-1-yl)-[1,2,4]-triazolo[l,5-a] Pyrimidine; -5 - murine-6-(2,5-dioxa-4-methylphenyl)-7-(3-methylhexazone 0 to bite-1-yl)-[1,2,4 ]-Triazolo[l,5-a]pyrimidine; _ 5 -Ga-6 - ( 2,5 -digas-4 -decyloxyphenyl)-7 - (3 -mercapto-six-rat ratio -1 ·yl)_[ 1,2,4]·Triazolo[1,5-a]pyrimidine; 118620.doc -10- 200800026 -5-methyl_6-(2,5_difluoro_4- -methoxyphenyl)-7-(3 • Methyl hexahydroquinone -methylhexahydropyridin-5-cyano-6-(2,5-difluoro_4-methoxyphenyl)_7·(3 pyridine-1-yl)_[1,2,4]-triazole And [^-...pyrimidine; -methylhexahydropyridin-6-(2,5-difluoro-t-methoxyphenyl)_7_(azepane + base) [1,2,4]triazole And -[i,5-a]pyrimidine; Base)-[1,2,4]二峻弁- [1,5-a]17 密唆; 1-based)-[1,2,4]di-sigma-salt-[i,5-a]-biting; -5-cyano-6-(2,5-difluoro-4-methoxyphenyl) )_7_(azepane-bu)-[1,2,4]triazino-[l,5-a] bite; -5-gas-6-(2,5-difluoro-4 -methylphenyl)-7-(azetidinyl[1,2,4]triazino-[l,5-a]-biting; -5-methyl-6-(2,5- Difluoro-4-indolylphenyl)-7-(azepane +yl)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy-6- (2,5-Difluoro-4-mercaptophenyl)-7-(azepan-yl)-[1,2,4]triazino-[l,5-a]-feeding; 5-cyano-6-(2,5-difluoro-4-mercaptophenyl)-7-(azepine a·fu) [1,2,4]triazolo-[l,5 -a]pyrimidine; -5-gas-6-(2,5-dioxa-4-methoxyphenyl)-7-(cyclopropylamino)[1,2,4]triazolo-[ l,5-a]pyrimidine; 118620.doc -11- 200800026 -5-methyl-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclopropylamino)- [1,2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclopropyl Amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methoxyphenyl)-7 -(cyclopropylamine -[1,2,4]triazolo-[l,5-a]pyrimidine; -5-gas-6-(2,5-difluoro-4-mercaptophenyl)-7-(cyclo) Propylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methyl-6-(2,5-dioxa-4-methylphenyl)- 7-(cyclopropylamino)_[1,2,4]triazino-[l,5-a] oxime; -5-methoxy-6-(2,5-difluoro-4- Nonylphenyl)-7-(cyclopropylamino)-[1,2,4]triazino-[l,5-a] continuous biting; -5-gasyl-6-(2,5- Diox-4-methylphenyl)-7-(cyclopropylamino)·[1,2,4]triazolo-[l,5-a]pyrimidine; -5·gas-6-(2 ,5-dioxa-4-methoxyphenyl)-7-(3⁄4-hexylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-fluorenyl- 6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclohexylamino)-[1,2,4]triazolo-[IJ-a]pyrimidine; -5-A Oxy-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclohexylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine -5-Cyano-6-(2,5-difluoro-4-methoxyphenyl)_7-(cyclohexylamino)-[1,2,4]triazolo-[l,5- a]pyrimidine; -5 -murine-6-(2,5-dioxa-4-methylphenyl)-7-(3⁄4 hexylamino)-[1,2,4]triindole-[1, 5-a]pyrimidine 118620.doc -12- 200800026 -5-mercapto-6-(2,5-difluoro-4-methylphenyl)-7-(cyclohexylamino)-[1,2,4]triazole And -[l,5-a]pyrimidine; 5·decyloxy-6-(2,5-difluoro-4-methylphenyl)-7-(cyclohexylamino)-[1,2,4 Triazolo-[l,5-a]pyrimidine; 5-cyano-6-(2,5-difluoro-4-indolylphenyl)-7-(cyclohexylamino)-[1,2 , 4] triazolo-[l,5-a]pyrimidine; 5-chloro-6-(2,5-difluoro-4-methoxyphenyl)-7-(cyclodecylamino)_ [ 1,2,4]triazolo-[l,5-a]pyrimidine; 5-methyl-6-(2,5-diox-4-methoxyphenyl)-7-(cyclopentylamine (), [1,2,4]triazolo-[l,5-a]pyrimidine; 5-methyllacyl-6-(2,5-difluoro-4-decyloxyphenyl)-7- (3⁄4戍ylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-carbyl-6-(2,5-dioxin-4-methoxybenzene -7-(cyclodecylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; 5-chloro-6-(2,5-difluoro-4-methyl Phenyl)-7-(cyclopentylamino)-[1,2,4] triwax-[l,5-a] bite; 5-methyl-6-(2,5-dual -4-methylphenyl)-7-(cyclodecylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; 5-methoxy-6-(2, 5-difluoro-4- Methylphenyl)-7-(cyclodecylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; 5-cyano-6-(2,5-difluoro -4-methylphenyl)-7-(cyclopentylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; 5- gas-6-(2,5- Di-(4-methylphenyl)-7-(N-(2-mercaptopropyl-1 yl)ethylamino)-[1,2,4]triazolo-[l,5- a]pyrimidine; 118620.doc -13- 200800026 -5-mercapto-6-(2,5-difluoro-4-mercaptophenyl)-7_(N_(2·methacryl_Γ_yl)-Ν -ethyl &c base)-[1,2,4]diindole_[i,5-a] re-biting; -5-decyloxy-6-(2,5-difluoro-4-indole Phenyl)-7-(N_(2_mercaptopropenyl-1-yl)-N-ethylamino)-[1,2,4]triazino-[i,5-a] oxime; 5-cyano-6-(2,5·difluoro-4·methylphenyl)·7_(Ν_(2-methylpropenyl)ethylamino)-[1,2,4]trisodium And -[1,5-&] spray-setting; -5-chloro-6-(2,5-difluoro-4-decyloxyphenyl)_7_(Ν_(2_methacrylic small group)- Ν-ethylamino)-[1,2,4]tris-[i,5-a]♦ bite; -5-methyl-6-(2,5-difluoro-4-methoxy Phenyl)-7-(N-(2-mercaptopropenyl-1-yl)-1^-ethylamino)-[1,2,4]triindole-[1,5 *^] mouth 唆; -5-methoxy-6-(2,5-difluoro-4-methoxyphenyl)-7-(N-(2-methylpropenyl-bu)-N- Ethylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methoxyphenyl)-7 -(N-(2-methylpropen-1-yl)-N-ethylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6 -(2,5·difluoro-4-methylphenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo-[l,5- a]pyrimidine; -5-methyl-6-(2,5-difluoro-4-methylphenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4 Triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-methylphenyl)-7-(2,2,2-trifluoroethyl Amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methylphenyl)-7- (2,2,2-trifluoroethylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro- 4-methoxyphenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; 118620.doc - 14- 200800026 -5-Methyl-6-(2,5-difluoro-4-methoxyphenyl)-7-(2,2,2-trifluoroethylamino Hl,2,4]3 Oxazo-[l,5-a]pyrimidine; -5-oxime -6-(2,5-difluoro_4-methoxyphenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo-[l , 5-a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-mercaptophenyl)-7-(2,2,2-trifluoroethylamino)-[ 1,2,4]triazolo-[l,5-a]pyrimidine; -5-methyl-6-(2,5-difluoro-4-decyloxyphenyl)-7-((1,2,2 -trimethylpropan-1-yl)amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5-difluoro- 4-methoxyphenyl)-7-((1,2,2-trimethylprop-1-yl)amino)-[1,2,4]triazolo-[l,5-a] Pyrimidine; -5-decyloxy-6-(2,5-difluoro-4-yloxyphenyl)-7-((1,2,2-trimethylpropan-1-yl)amino) -[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro^-4-methylphenyl)-7-(1 , 2,2-dimethylpropan-1-yl)amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methyl-6-(2,5 -dimethyl-4-methylphenyl)-7-((1,2,2-trimethylpropan-1-yl)amino)-[1,2,4]triazolo-[l,5 -a]pyrimidine; -5-cyano-6-(2,5-difluoro*-4-methylphenyl)-7-((1,2,2-trimethylpropan-1-yl)amine Base)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5- Oxy-6-(2,5-dioxa-4-mercaptophenyl)-7-((1,2,2-trimercaptopropen-1-yl)amine Hl,2,4]triazole -[l,5-a]pyrimidine; -5 -mur-6-(2,5-dioxa-4-methylphenyl)-7-((1,2,2-dimethylpropan-1) Amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro-4-methylphenyl)-7 -(1,2-dimethylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; 118620.doc -15- 200800026 -5-methyl-6- (2,5-difluoro-4-mercaptophenyl)-7-(l,2-dimethylpropylamino)-[1,2,4]triazolo-[l,5-a] Pyrimidine; -5-methoxy-6-(2,5-difluoro-4-methylphenyl)-7-(1,2-dimercaptopropylamino)-[1,2,4] Triazolo-[l,5-a]pyrimidine; -5-carbyl-6-(2,5-difluoro-4-methylphenyl)-7-( 1,2-dimethylpropyl Amino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2,5-difluoro-4-methoxyphenyl)-7- (1,2-dimethylpropylamino H1,2,4]triazolo-[l,5-a]pyrimidine; -5-methyl-6-(2,5-difluoro-4-methyl Oxyphenyl)-7-(1,2-dimethylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy- 6 - (2 5-difluoro-4-yloxyphenyl)-7-(1,2-dimethylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5 - murine- 6-(2,5-diox-4-methoxyphenyl)-7-(1,2-dimercaptopropylamino)-[1,2,4]triazole And -[l,5-a]pyrimidine; -5-gas-6-(2,5-di-gas-4-methylphenyl)-7-(1-mercaptopropylamino)·[1, 2,4]triazolo-[l,5-a]pyrimidine; -5-methyl-6-(2,5-dioxa-4-methylphenyl)-7-(1-methylpropyl Amino)_[1,2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-methylphenyl)- 7-(1-methylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5-difluoro-4 -methylphenyl)-7-(1-methylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-chloro-6-(2, 5-difluoro-4-indolylphenyl)-7-(1-methylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; I18620.doc -16- 200800026 -5-Mercapto-6-(2,5-difluoro-4-decyloxyphenyl)-7-(1-mercaptopropylamino)-[1,2,4] Zydro-[l,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-methoxyphenyl)-7-(1-methylpropylamine -[1,2,4]triazolo-[Ua]pyrimidine; -5-cyano-6-(2,5-difluoro-4-methoxyphenyl)-7-(1-oxime Propylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-gas-6-(2,5-difluoro-4-mercaptophenyl)- 7-(2-amidopropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-mercapto-6-(2,5-difluoro-4 -nonylphenyl)-7-(2-methylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-decyloxy-6-(2, 5-difluoro-4-indolylphenyl)-7-(2-methylpropylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5 - Cyano-6-(2,5-dioxa-4-methylphenyl)-7-(2-methylpropylamino)-[1,2,4]triazolo-[l,5- a]pyrimidine; -5-chloro-6-(2,5-diox-4-methoxyphenyl)-7-(2-mercaptopropylamino)-[1,2,4]triazole And -[l,5_a]pyrimidine; -5·methyl-6-(2,5-difluoro*-4-methoxyphenyl)-7-(2-methylpropylamino)-[1 , 2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2,5-di-rhos-4-methoxyphenyl)-7-(2-A Propylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-carbyl-6-(2,5-diox-4-methoxyphenyl )-7-(2- Propylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; /-5-chloro-6-(2,5-difluoro_4-methylphenyl)- 7-(2,2,3,3,4,4,4-heptafluorobutylamino H1,2,4]triazolo-[l,5-a]pyrimidine; 118620.doc -17- 200800026 - 5-methyl-6-(2,5-difluoro-4-methylphenyl)-7-(2,2,3,3,4,4,4-heptafluorobutylamino)-[1 , 2,4]triazolo-[l,5-a]pyrimidine; -5-methoxy-6-(2,5-difluoro-4-methylphenyl)_7-(2,2,3,3, 4,4,4-heptafluorobutylamino)-[1,2,4]triazolo-[l,5-a]pyrimidine; -5-cyano-6-(2,5.difluoro- 4-nonylphenyl)-7-(2,2,3,3,4,4,4-heptafluorobutylamino)-[1,2,4]triazolo-[l,5-a Pyrimidine; -5-gas-6-(2,5-difluoro-4-decyloxyphenyl)-7-(2,2,3,3,4,4,4-heptafluorobutylamine Hl , 2,4]triazolo-[l,5-a]pyrimidine; -5-methyl-6-(2,5-difluoro-4-methoxyphenyl)-7_(2,2,3 ,3,4,4,4-heptafluorobutylamino H1,2,4]triazolo-[l,5-a]pyrimidine; -5-decyloxy-6-(2,5-difluoro -4-decyloxyphenyl)-7-(2,2,3,3,4,4,4-heptafluorobutylamino)-[1,2,4]triazolo-[l,5 -a]pyrimidine; -5-cyano-6-(2,5-difluoro-4-decyloxyphenyl)-7·(2,2,3,3,4,4,4 - Heptafluorobutylamino)·[1,2,4]triazolo-[l,5-a]pyrimidine; and agriculturally acceptable salts thereof. 22_ — the three types of the formula iv and the mouth, Wherein the substituents L1 and L2 are as defined in claim 1 and Halft _ and especially chlorine, wherein L2 is F and L1 is a methoxy group Except 23·-type of triazole and feeding, 118620.doc -18- 200800026 A compound of the formula V as defined in the first aspect and wherein Hal is a halogen methoxy group, wherein the substituents L1 and L2 are as defined, and especially chlorine, wherein the L2 is a tetrazole of the formula Iva. Pyrimidine, L2 (IVa) wherein the substituents L and L2 are as defined in the claim χ and the oxime is Ci-C4_alkyl. 25. —Triazolopyrimidine of the formula Va, L2 (Va) wherein the substituents L1 and L2 are as defined in claim 1 and Hal is halogen and especially chlorine' and burned. 118620.doc -19- 200800026 VII. Designated representative map: (1) The representative representative of the case is: (none) (2) The symbol of the symbol of the representative figure is simple: 8. If there is a chemical formula in this case, please reveal the best display. Chemical formula of the inventive feature: (I) 118620.doc