TH58697A - The salt of evermectin is replaced at the 4" position and has pesticide properties. - Google Patents

Abstract

DC60 is a compound with the formula (chemical formula) (I) where X- is an anion; n is 1, 2, 3 or 4; R1 is C1-C12 alkyl, C3-C8 cycloalkyl, or C2-C12 alkinyl; R2 is hydrogen, C1-C12 alkyl, C2-C12 unsubstituted or substituted alkinyl; R3 is hydrogen, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 alkinyl or C2-C12 unsubstituted or substituted alkynyl; or R2 and R3 together are an alkylene or alkyneline bridge; and when applicable are E/Z isomers, mixtures of E/Z isomers and/or twotomers; Providing that R1 is not sec-butyl or isopropyl, R2 is H and R3 is methyl; and when applicable, their possible tutomers; the processes for the preparation of these compounds and their tutomers and their applications; the pesticide formulations in which the active ingredient is selected from these compounds and their tutomers; and the processes for the preparation of these components and their applications; intermediates, in free form or in salt form, for the preparation of these compounds and, when applicable, their tutomers. In its free form or in its salt form, compounds with the formula (chemical formula) (I), where X is an anion; n is 1, 2, 3, or 4; R1 is C1-C12 alkyl, C3-C8 cycloalkyl, or C2-C12 alkynyl; R2 is hydrogen, C1-C12 alkyl, C2-C12 unsubstituted or substituted alkynyl; R3 is hydrogen, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 alkynyl, or C2-C12 unsubstituted or substituted alkynyl; or R2 and R3 together are alkylene or alkyniline bridges; and when applicable are E/Z isomers, mixtures of E/Z isomers and/or twototers; Providing that R1 is not sec-butyl or isopropyl, R2 is H and R3 is methyl; and when applicable, their possible tutomers; the processes for the preparation of these compounds and their tutomers and their uses; pesticide mixtures in which the active ingredient is selected from these compounds and their tutomers; and the processes for the preparation of these mixtures and their uses; intermediates, in free form or in salt form, for the preparation of these compounds, and when applicable, their tutomers, in free form or in salt form, are described.

Claims (9)

1. Compounds with the formula (chemical formula) (I) where X is an anion; n is 1, 2, 3, or 4; R1 is a C1-C12 alkyl, C3-C8 cycloalkyl, or C2-C12 alkynyl; R2 is hydrogen, unsubstituted or 1 to 5 substituted C1-C12 alkyls, unsubstituted or 1 to 5 substituted C2-C12 alkynyls; R3 is hydrogen, unsubstituted or 1 to 5 substituted C1-C12 alkyls, unsubstituted or 1 to 5 substituted C3-C12 cycloalkyls, unsubstituted or 1 to 5 substituted C2-C12 alkynyls, unsubstituted or 1 to 5 substituted C2-C12 alkynyls. The position; or R2 and R3 together; is an alkylene bridge with 3 to 7 atoms, or an alkiniline bridge with 4 to 7 atoms, in which the -CH2- group may be replaced by O, S, or NR4; and the substituent groups of the alkyl, alkinyl, aldynyl, alkylene, alkiniline, and cycloalkyl radicals mentioned are selected from groups containing OH, halogen, halo-C1-C2 alkyl, CN, NO2, C2-C8 alkynyl, C3-C8 cycloalkyl, norbornelinyl, C3-C8 cycloalkinyl; C3-C8 cycloalkinyl. Unreplaced or replaced by 1 to 3 methyl groups; C3-C8 halocycloalkyl, C1-C12 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C3-C8 cycloalkoxy, C1-C12 haloalkoxy, C1-C12 alkylthio, C3-C8 cycloalkylthio, C1-C12 haloalkylthio, C1-C12 alkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C12 haloalkylsulfinyl, C3-C8 halocycloalkylsulfinyl, C1-C12 alkylsulfonyl, C3-C8 cycloalkylsulfonyl. C1-C12 haloalkylsulfonil, C3-C8 halocycloalkylsulfonil, C2-C8 alkinil, C2-C8 alkynil, NH(C1-C6 alkyl), N(C1-C6 alkyl)2, -C(=O)R5, -NHC(=O)R8, -P(=O)(OC1-C6 alkyl)2; aryl, heterocyclyl, aryloxy, heterocyclyloxy; and aryl, heterocyclyl, aryloxy and heterocyclyloxy This depends on the possibility of substitution at 1 to 5 positions, with the chosen substituent group consisting of OH, halogen, CN, NO2, C1-C12 alkyl, C3-C8 cycloalkyl, C1-C12 haloalkyl, C1-C12 alkoxy, C1-C12 haloalkoxy, C1-C12 alkylthio, C1-C12 haloalkylthio, C1-C6 alkoxy-C1-C6 alkyl, dimethylamino-C1-C6 alkoxy, C2-C8 alkynyl, C2-C8 alkynyl, phenoxy, phenyl-C1-C6 alkyl; Unsubstituted phenoxymethyl group, or substituted by one to three independently selected substituents from halogenated, methoxymethyl, trifluoromethyl, and trifluoromethoxymethyl groups; unsubstituted or substituted in the aromatic ring by one to three independently selected substituents from halogenated, methoxymethyl, trifluoromethyl, and trifluoromethoxymethyl groups; Phenyl-C2-C6 alkynyl, Phenyl-C2-C6 alkynyl, Methylenedioxy, -C(=O)R5, -O-C(=O)R6, -NH-C(=O)R6, NH2, NH(C1-C12 alkyl), N(C1-C12 alkyl)2, C1-C6 alkylzephenyl, C3-C8 cycloalkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 halocycloalkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 haloalkylsulfonyl and C3-C8 halocycloalkylsulfonyl; R4 is C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkynyl, C2-C8 alkynyl, benzyl or -C(=O)-R5; R5 is H, OH, SH, NH2, NH(C1-C12 alkyl), N(C1-C12 alkyl)2, C1-C12 alkyl, C1-C12 haloalkyl, C1-C12 alkoxy, C1-C12 haloalkoxy, C1-C6 alkoxy-C1-C6 alkoxy, C1-C12 alkylthio, C2-C8 alkynyloxy, C2-C8 alkynyloxy; Phenyl, phenoxy, benzyloxy, -NH-phenyl, -N(C1-C8 alkyl)-phenyl, NH-C1-C6 alkyl-C(=O)-R7, -N(C1-C6 alkyl)-C1-C6- alkyl-C(=O)-R7; or phenyl, phenoxy, benzyloxy, NH-phenyl or -N(C1-C8 alkyl)-phenyl that is substituted in the aromatic ring. The first to third substituent groups are independently selected from halogens, C1-C6 alkoxy, C1-C6 haloalkyl, and C1-C6 haloalkyl; R6 is H, C1-C12 alkyl, C1-C12 haloalkyl, C2-C8 alkinyl, C2-C8 alkynyl, phenyl, benzyl, NH2, NH(C1-C12 alkyl), N(C1-C12 alkyl)2, -NH-phenyl, or -N(C1-C12 alkyl)-phenyl; And R7 is H, OH, C1-C12 alkyl, C1-C12 alkoxy, C1-C6 alkoxy-C1-C6 alkoxy, C2-C8 alkynyloxy, phenyl, phenoxy, benzyloxy, NH2, NH(C1-C12 alkyl), N(C1-C12 alkyl)2, -NH-phenyl or -N(C1-C12 alkyl)-phenyl; and when used as E/Z isomers, mixtures of E/Z isomers and/or twototers; provided that R1 is not sec-butyl or isopropyl, where R2 is H and R3 is methyl; 2. The compound under claim 1 with the formula (I), where R1 is isopropyl or sec-butyl. 3. A pesticide mixture containing at least one compound under claim No. 1, formulated (I) in its free form or in an agrochemically acceptable salt form as the active ingredient, and at least one adjuvant. 4. Methods of pest control consisting of the application of the compounds specified in claim 3 to the pests or to the locations where they are found. 5. The process for preparing the mixtures under claim 3, which contain at least one synergistic agent, involves the mixing and/or thorough grinding of the active ingredient with the synergistic agent. 6. The use of the compounds under claim 1 with the formula (I) in their free form or in a chemically acceptable salt form in the preparation of mixtures described in claim 3. 7. The use of the mixtures as per claim 3 for pest control. 8. The method under claim number 4 for the protection of plant propagation material, which includes the treatment of the propagation material or the cultivation area of the propagation material. 9. Plant propagation materials treated according to the methods described in claim 8.