Herbicide / safener combinations based on substituted [(1, 5-diphenyl-1h-1, 2, 4-triazol-3-yl) oxy] acetic acid safeners and substituted cyclic diketone herbicides and salts thereof
By combining [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives with substituted cyclic diketone herbicides, the problems of limited stability and protection range in combined use have been solved, achieving effective protection and weed control for a variety of crops.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- BAYER AG
- Filing Date
- 2024-07-04
- Publication Date
- 2026-05-08
AI Technical Summary
The combined use of existing herbicides and safeners presents stability issues, decomposition of active ingredients, and antagonistic phenomena. Furthermore, the protective range of safeners is limited and they cannot effectively protect a variety of crops.
Combinations of [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and their salts with substituted cyclic diketone herbicides are used to protect crop plants from unwanted plant growth.
It effectively protects a variety of crops such as wheat, corn, and soybeans, ensuring that the efficacy of herbicides is not affected, and improving the stability and protection range of combined use.
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Figure CN122003172A_ABST
Abstract
Description
[0001] This invention relates to the technical field of crop protection compositions, which can be used to inhibit the growth of unwanted plants on cultivated land, for seed preparation, or for use in plant crops. The compositions comprise a combination of at least one safener (A) and at least one herbicide (B), wherein the safener (A) is one or more substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid and / or an agriculturally chemically acceptable salt of general formula (I) (= component (A)).
[0002] Known herbicides are highly effective against harmful plants; however, their effectiveness often depends on the application rate, the form of the formulation, the spectrum of harmful plants, the harmful plants to be controlled in each case, climate and soil conditions, and especially on the compatibility of the crop with the plant.
[0003] One approach to improving the application characteristics of herbicides might be to combine a safener with one or more active herbicidal ingredients that provide the desired additional properties. However, physical and biological incompatibilities are not uncommon in the combined application of two or more active ingredients, such as a lack of stability in the combined formulation, decomposition of the active ingredients and / or antagonism between them, or a limited scope of action of the safener, which may only protect the crop from one herbicide but not be effective against all components in the combined application of two or more herbicides.
[0004] Safeners (also known as antidotes) with different chemical structures have been known for approximately 70 years. It is also known that they differ significantly in their protective function, meaning their use is limited to selected herbicides and / or the crop plants requiring protection. Furthermore, based on the harmful plant to be controlled, the selected herbicide / safener combination must not adversely affect weed control efficacy.
[0005] [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and their salts are known in PCT application No. PCT / EP2020 / 083167 (WO2021 / 105101). Substituted cyclic diketones and their salts are known, for example, in PCT application No. WO2021009229.
[0006] It has now been found that substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid compounds can indeed be effectively used to protect different crop plants when applied simultaneously with one or more substituted cyclic dione herbicides [hereinafter referred to as "component (B)"].
[0007] The herbicide / safety agent combinations of the present invention interact in a particularly advantageous manner when used to control unwanted plant growth in crop plants such as wheat (durum and soft wheat), corn, soybean, sugar beet, sugarcane, cotton, rice, legumes (e.g., bush beans and broad beans), flax, barley, oats, rye, triticale, potatoes, and millet / sorghum.
[0008] Therefore, the present invention provides a combination comprising one or more active components (A) as safeners and one or more herbicidal active compounds as components (B), wherein (A) represents one or more compounds of general formula (I) or an agriculturally chemically acceptable salt thereof. And among them, (R a ) p -Phenyl groups represent Q-1.1 to Q-1.55 groups: And (R) b ) q -Phenyl represents a group from Q-2.1 to Q-2.55: R c It is hydrogen. and R dThe following are compounds: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-yl-methyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalic acid Ester-3-yl, methyl-2-methylpropionate-3-yl, methyl-2,2-dimethylpropionate-3-yl, ethyl-2-methylpropionate-3-yl, methyl-2-propionate-2-yl, ethyl-2-propionate-2-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetane-3-yl, (3-methyloxetane-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-di Fluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropyl-ethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propyne (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2 -en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptane-2-yl, isobutyl, 1,3-dioxolane-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl and (B) represents one or more compounds having the general formula (II) or their agrochemically acceptable salts. in Q is selected from Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-1 7. Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-29, Q-30, Q-31 and Q-32, The arrow The dashed line represents the linking bond between a carbon atom and a Z group. This indicates a linking bond between a carbon atom and a W group; R 1 It is a methyl, ethynyl, 1-propynyl, phenyl, or a five- or six-membered heteroaromatic ring containing one or two nitrogen atoms, wherein the benzene ring and the heteroaromatic ring can be represented by one or two R atoms. 9 Group substitution, R 2 It can be chlorinated, (C1-C3)-alkoxy, (C1-C2)-alkoxy-(C1-C3)-alkoxy, (C1-C2)-fluoroalkoxy, methyl, ethyl, n-propyl, n-butyl, cyclopropyl, or ethynyl. R 3 It can be hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, (C1-C3)-alkoxy, (C1-C3)-fluoroalkyl, (C1-C2)-fluoroalkoxy, (C1-C2)-alkoxy-(C1-C3)-alkoxy, or C1-fluoroalkoxy-(C1-C3)-alkoxy. W is the connection key, CR 4 R 5 , O, NH or N-CH3, Z is the connection key, CR 6 R 7 , O, NH or N-CH3, The condition is that W and Z cannot both be connect keys. Y is O or NR 8 , n1 and n2 are independently 0, 1, 2 or 3, with the condition that n1 + n2 = 2, 3, 4, 5 or 6. R1Q3 It is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy-(C1-C3)-alkyl, or (C1-C6)-haloalkoxy-(C1-C3)-alkyl. R 2Q3 -(CH2) k -R 3Q3 , Where R 3Q3 Selected from -C(O)NR 5N R 6N -NR 5N R 6N and -S(O)2NR 16N R 17N , And k is 0, 1, or 2. Or R 1Q3 and R 2Q3 Together for -(CH2) nq1 -C(R 4Q3 )R 5Q3 -(CH2) nq2 - where nq1 and nq2 are independently 1 or 2, R 4Q3 It is hydrogen, (C1-C6)-alkyl, hydroxyl, methoxy, or halogen. R 5Q3 Selected from -C(O)NR 5N R 6N -NR 5N R 6N and -S(O)2N R16N R 17N , Or R 4Q3 and R 5Q3 Together for -(CH2) nq3 -N(R 8 )-(CH2) nq4 - where nq3 and nq4 are independently 1 or 2. R 1Q10 and R 2Q10 Independently selected from hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, and (C1-C3)-alkoxy. Y p Selected from O, CR Y1 R Y2 and NR Y3 , Where R Y1 It is hydrogen or (C1-C4) alkyl. R Y2 It is hydrogen or (C1-C4) alkyl. R Y3 Selected from hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, -(CO)(C1-C4)-alkyl and -(CO)(C1-C4)-halogenated alkyl; Y q For N or CH, R 4 R 5 R 6 and R 7 Each of the following is independently hydrogen, (C1-C5)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C2)-fluoroalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkylthio-(C1-C3)-alkyl, (C1-C3)-alkylsulfinyl-(C1-C3)-alkyl, (C1-C3)-alkylsulfonyl-(C1-C3)-alkyl, (C3-C4)-cycloalkyl, or an unsubstituted 4-, 5-, or 6-membered monocyclic heterocyclic ring, having a cyclic heteroatom selected from oxygen, sulfur, or nitrogen and attached to a cyclic carbon atom within the heterocyclic group, under the condition R 4 R 5 R 6 and R 7 No more than one of the groups is an alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl, or heterocyclic group. Or R 4 and R 5 Together they form -(CH2) n3 -or-(CH2) n4 -X 1 -(CH2) n5 - group, and R 6 and R 7 As defined above, Or R 6 and R 7 Together they form -(CH2) n3 -or-(CH2) n4 -X 1 -(CH2) n5 - group, while R 4 and R 5 As defined above, Where X 1 For O (oxygen), S (sulfur), S (O), S (O)2, N (R) 8 ), C(H)((C1-C2)-alkyl), C((C1-C2)-alkyl)2 or C(H)((C1-C2)-alkoxy); n3 is 2, 3, 4, or 5. n4 and n5 are independently 1, 2, or 3, provided that n4 + n5 = 2, 3, or 4. Or R 5 and R 6 Together they form -(CH2) n6 -or-(CH2) n7 -C(R 10a (R) 10b )-(CH2) n8 -or-C(R) 10c )=C(R 10d )- group, wherein R 10a It is (C1-C2)-alkyl or (C1-C2)-alkoxy; and R 10b It is hydrogen or (C1-C2)-alkyl, under the condition that R 10a When it is (C1-C2)-alkoxy, R 10b The form is hydrogen, where n6 is 1, 2, or 3, n7 and n8 are independently 0, 1, or 2, provided that n7 + n8 = 0, 1, or 2, and where R 10c and R 10d Independently hydrogen or (C1-C2)-alkyl, R 8 It is hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, -C(O)(C1-C4)-alkyl, -C(O)(C1-C4)-haloalkyl, -S(O) n (C1-C6)-alkyl, -S(O) n (C1-C6)-Haloalkyl, -S(O) n -(CH2) n -(C3-C6)-cycloalkyl, -S(O) n C(R 11N )R 12N R 13N -C(O)H, -C(O)-(CH2) n -(C3-C6)-cycloalkyl, -C(O)C(R 11N )R 12N R 13N -C(O)(C2-C4)-alkenyl, -C(O)(CR 9N R 10N )CN、 -C(O)(CR 9N R 10N (CR) 9N R 10NCN, -C(O)CH2C(O)-(C1-C6)-alkyl, -C(O)CH2OC(O)-(C1-C6)-alkyl, -C(O)O(C1-C6)-alkyl, -C(O)O(C1-C6)-haloalkyl, -C(O)(CH2) n S(O) n (C1-C6)-alkyl, -C(O)(C1-C3)-alkoxy-(C1-C6)-alkyl, -C(O)(C1-C3)-alkoxy-(C2-C6)-alkenyl, -C(O)(C1-C3)-alkoxy-(C2-C6)-alkynyl, -C(O)(C1-C3)-alkoxy-(C1-C6)-haloalkyl, -C(O)(C1-C3)-alkoxy-(C3-C6)-cycloalkyl, -C(O)O(C1-C3)-alkoxy-(C1-C6)-alkyl, -C(O)(C1-C3)-alkoxy-(C1-C3)-alkoxy-(C1-C6)-alkyl, -C(O)(CH2)nNR 5N R 6N -C(O)-(CH2)n-NR 7N C(O)R 8N , -C(O)-(CH2) n -ON=CR 5N R 5N -CN, -S(O)2NR 16N R 17N -S(O)(=NR) 18N )R 19N -C(O)C(O)R 20N , -C(O)C(R 23N )=NOR 24N -C(O)C(R) 23N )=N-NR2 5N R 26N -(CH2) n -Phenyl, -C(O)-(CH2) n -phenyl, -S(O) n -(CH2) n -Phenyl, heterocyclic, -C(O)-(CH2) n -Heterocyclic group, -C(O)(CH2) n -O-(CH2) n -heterocyclic group, -S(O) n -(CH2) n- Heterocyclic groups, wherein each heterocyclic group is a five- or six-membered heterocyclic ring, which may be aromatic, saturated or partially saturated, and may contain one to four heteroatoms, wherein each heteroatom is independently selected from oxygen, nitrogen and sulfur, and wherein the heterocyclic ring or benzene ring may optionally be substituted by one, two or three substituents independently selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 9 This indicates a substituent independently selected from (C1-C4)-alkyl, (C1-C4)-haloalkyl, cyano, and halogen groups; R 5N This indicates substituents independently selected from hydrogen and (C1-C6)-alkyl groups. R 6N The expression indicates that the group is independently selected from hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-haloalkyl, hydroxyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, -(C1-C4)-alkoxy-(C1-C6)-alkyl, -(C1-C3)-alkoxy-(C1-C6)-haloalkyl, -(CR 9N R 10N )-(C1-C6)-haloalkyl, -(CR 9N R 10N )C(O)NR 5N R 5N -C(O)H, -C(O)-(CH2) n -(C3-C6)-cycloalkyl, -C(O)-(CH2) n -C(R 11N )R 12N R 13N Substituents of phenyl and pyridyl, wherein the benzene ring and pyridyl ring are optionally substituted by one, two, or three independent substituents selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano, and nitro; or R 5N and R 6N Together they form -CH2CH2OCH2CH2-; and R 7N Selected from hydrogen and (C1-C6)-alkyl; R 8NThe group is selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, phenyl, pyridyl, wherein the benzene ring and pyridyl ring are optionally substituted by 1, 2 or 3 independent substituents selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 9N It can be hydrogen or methyl; R 10N It is hydrogen or methyl; or R 9N and R 10N Together they form -CH2CH2-; and R 11N It can be hydrogen or methyl; R 12N Selected from hydrogen, (C1-C6)-alkyl, hydroxyl, and (C1-C6)-alkoxy; R 13N Selected from hydrogen, (C1-C6)-alkyl, hydroxyl, and (C1-C6)-alkoxy; or R 12N and R 13N Together they form -CH2-X-CH2-; and X is selected from O, S, and NR. 14N ; R 14N Selected from hydrogen, (C1-C3)-alkyl, and (C1-C3)-alkoxy; R 16N It is hydrogen or (C1-C6)-alkyl; and R 17N Selected from hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy-(C1-C3)-alkyl, -C(O)(C1-C6)-alkyl, -C(O)O(C1-C6)-alkyl, and CH2CN; or R 16N and R 17N Together they form -CH2CH2OCH2CH2- and -CH2CH2S(O)2CH2CH2-; R 18N It is hydrogen or (C1-C6)-alkyl; R 19NThe group is selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, phenyl, pyridyl, wherein the benzene ring and pyridyl ring are optionally substituted by 1, 2 or 3 independent substituents selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 20N Selected from (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, -NR 21N R 22N , phenyl, pyridyl, wherein the benzene ring and the pyridyl ring may optionally be substituted by one, two or three independent substituents selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 21N The group is selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl and (C1-C6)-haloalkoxy, -C(O)(C1-C6)-alkyl, phenyl, pyridyl, wherein the benzene ring and pyridyl ring may optionally be substituted by 1, 2 or 3 substituents independently selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 22N It is hydrogen or (C1-C6)-alkyl; or R 21N and R 22N Together they form -CH2CH2OCH2CH2-; R 23N Selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy; R 24N The group is selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, -CH2CN, tetrahydropyranyl, phenyl, pyridyl, wherein the benzene ring and pyridyl ring may optionally be substituted by 1, 2 or 3 substituents independently selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R25N It is hydrogen or (C1-C6)-alkyl; R 26N It is hydrogen or (C1-C6)-alkyl; n can be 0, 1, or 2 independently; G represents hydrogen, a chemically acceptable metal, a chemically acceptable sulfonium group, a chemically acceptable ammonium group, or C(X). 3 )-R 14 -C(X) 4 )-X 5 -R 15 -C(X) 6 )-N(R 16 )-R 17 -SO2-R 18 -P(X) 7 (R) 19 )-R 20 , -CH 2 -X 8 -R 21 (C1-C6)-alkoxy-C(O)-CH2-, (C1-C6)-alkoxy-C(O)-CH=CH-, (C2-C7)-en-1-yl-CH2-, (C2-C7)-en-1-yl-CH[(C1-C2)-alkyl]-, (C2-C4)-fluoroen-1-yl-CH2-, (C2-C7)-yn-1-yl-CH2-, (C2-C7)-yn-1-yl-CH[(C1-C2) -alkyl]-, heteroaryl-CH2-, heteroaryl-CH[(C1-C2)-alkyl]-, phenyl-CH2-, phenyl-CH[(C1-C2)-alkyl]-, phenyl-C(O)-CH2- groups, wherein the phenyl or heteroaryl group is optionally and independently substituted by 1, 2 or 3 substituents selected from (C1-C2)-alkyl, C1-fluoroalkyl, (C1-C2)-alkoxy, C1-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, X 3 X 4 X 5 X 6 X 7 and X 8 Independently, it consists of O (oxygen) and S (sulfur). R 14 For hydrogen, (C1-C 21 )-alkyl, (C2-C 21 )-Alkenyl, (C2-C 18 )-Alkyne group, (C1-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C10 )-nitroalkyl, (C1-C 10 (C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenyloxy-(C1-C5)-alkyl, (C3-C5)-alkynyloxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)-alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminoalkylene (C1-C5)-alkyl 1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkyl, N-(C1-C5)-alkylcarbonyl-N-(C1-C5)-alkylamino(C1-C5)-alkyl, (C3-C6)-trialkylsilyl-(C1-C5)-alkyl, phenyl-(C1-C5)-alkyl, wherein the phenyl group It is also optionally and independently substituted with 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is also optionally and independently substituted with 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is also optionally and independently substituted with 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl The phenyl group is substituted with an acyl group, a (C1-C3)-alkylsulfonyl group, a fluorine group, a chlorine group, a bromine group, a cyano group, or a nitro group; or a (C2-C5)-fluoroalkenyl group, a (C3-C8)-cycloalkyl group; or a phenyl group independently substituted with one, two, or three groups selected from the following groups: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or a heteroaryl group or a heteroaryl group independently substituted with one, two, or three groups selected from the following groups: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro. R 15 For (C1-C 18 )-alkyl, (C3-C 18 )-Alkenyl, (C3-C 18 )-Alkyne group, (C2-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C2-C 10(C1-C5)-alkylamino(C1-C5)-alkyl, (C2-C8)-dialkylamino(C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenyloxy-(C1-C5)-alkyl, (C3-C5)-alkynyloxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)-alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminoylene (C1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkyl, N-(C1-C5)-alkylcarbonyl-N-(C1-C5)-alkylamino(C1-C5)-alkyl, (C3-C6)-trialkylsilyl-(C1-C5)-alkyl, phenyl-(C1-C5)-alkyl, wherein... The phenyl group is also optionally and independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is also optionally and independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl ... (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfin The phenyl group is substituted with 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, or nitro groups; or (C2-C5)-fluoroalkenyl, (C3-C8)-cycloalkyl groups; or a heteroaryl group is substituted with 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro groups; or a heteroaryl group is substituted with 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro groups. R 16 and R 17 Independently hydrogen, (C1-C10 )-alkyl, (C2-C 10 )-Alkenyl, (C2-C 10 )-Alkyne group, (C2-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C1-C 10(C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenyloxy-(C1-C5)-alkyl, (C3-C5)-alkynyloxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5) -alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminooxy(C1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)- Alkyl, N-(C1-C5)-alkylcarbonyl-N-(C1-C5)-alkylamino(C1-C5)-alkyl, (C3-C6)-trialkylsilyl-(C1-C5)-alkyl, phenyl-(C1-C5)-alkyl, wherein the phenyl group is optionally independently surrounded by 1, 2 or 3 radicals selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl The heteroaryl group is substituted with an acyl, fluorine, chlorine, bromine, cyano, or nitro group, and is (C1-C5)-alkyl, wherein the heteroaryl group is optionally and independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, or nitro groups, or (C2-C5)-fluoroalkenyl or (C3-C8)-cycloalkyl.The phenyl group or phenyl group is independently substituted by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, and nitro groups, or the heteroaryl group or heteroaryl group is independently substituted by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, and nitro groups, or the phenyl group is independently substituted by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, and (C1-C3)-fluoroalkoxy groups, The heteroaryl group is substituted with a fluorine, chlorine, bromine, cyano, or nitro group, or a heteroarylamino group, wherein the heteroaryl group is independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro group, or a diarylamino group, wherein each ...alkyl, (C1-C3)-fluoroalkyl, (C1-C3)-fluoroalkyl, or (C1-C3)-fluoroalkyl, (C1-C3)-fluoroalkyl, or (C1-C3)-fluoroalkyl, (C1-C3)-fluoroalkyl, or (C1-C3)-fluoroalkyl, (C1-C3)-fluoroalkyl, or (C1-C3)-fluoroalkyl, (C1-C3)-fluoroalkyl, or (C1-C3)-fluoroalkyl, The phenyl group is substituted with a group selected from (C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or phenylamino, wherein the corresponding phenyl group is independently replaced by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, alkyl, fluoroalkyl, ... The nitro group is substituted, or diphenylamino or diphenylamino, wherein each phenyl group is independently substituted by one, two or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or (C3-C7)-cycloalkylamino, di-[(C3-C7)-cycloalkyl]amino, (C3-C7)-cycloalkoxy; or; R 16 and R 17 Together with the nitrogen atoms they are attached to, they form an unsubstituted 4- to 7-membered ring, which may optionally contain heteroatoms from O (oxygen) and S (sulfur). R 18 For (C1-C 10 )-alkyl, (C2-C 10 )-Alkenyl, (C2-C 10 )-Alkyne group, (C1-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C1-C 10(C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenoxy-(C1-C5)-alkyl, (C3-C5)-alkynoxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)- Alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminooxy-(C1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl-(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkane The phenyl group is further optionally and independently surrounded by one, two or three groups selected from (C1-C3)-alkyl, (C1-C5)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1-C3)-alkylsulfonyl, etc. The heteroaryl group is substituted with a group of alkyl, fluorine, chlorine, bromine, cyano, or nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is optionally independently substituted by 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, or nitro, or (C2-C5)-fluoroalkenyl or (C3-C8)-cycloalkyl.The phenyl group or phenyl group is independently substituted by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, and nitro groups, or the heteroaryl group or heteroaryl group is independently substituted by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, and nitro groups, or the phenyl ... The heteroaryl group is substituted with a chlorine, bromine, cyano, or nitro group, or a heteroarylamino group, wherein the heteroaryl group is independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro groups, or a diarylamino group, wherein each heteroaryl group is independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro groups, or a diarylamino group, wherein each heteroaryl group is independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, bromine, cyano, or nitro groups. )-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, or phenylamino or phenylamino, wherein the corresponding phenyl group is independently replaced by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups. The phenyl group is substituted with a group, or diphenylamino or diphenylamino, wherein each phenyl group is independently substituted with 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or (C3-C7)-cycloalkylamino, di-[(C3-C7)-cycloalkyl]amino, (C3-C7)-cycloalkoxy, (C1-C; 10 )-alkoxy, (C1-C 10 (C3-C7)-fluoroalkoxy, (C3-C7)-alkylamino, di-[(C3-C7)-alkyl]amino; R 19 and R 20 Independently for (C1-C 10 )-alkyl, (C2-C 10 )-Alkenyl, (C2-C 10 )-Alkyne group, (C1-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C1-C 10(C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenoxy-(C1-C5)-alkyl, (C3-C5)-alkynoxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)- Alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminooxy-(C1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl-(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkane The phenyl group is further optionally and independently surrounded by one, two or three groups selected from (C1-C3)-alkyl, (C1-C5)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1-C3)-alkylsulfonyl, etc. The heteroaryl group is substituted with a group of alkyl, fluorine, chlorine, bromine, cyano, or nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is optionally independently substituted by 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, or nitro, or (C2-C5)-fluoroalkenyl or (C3-C8)-cycloalkyl.The phenyl group is independently substituted by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, and nitro groups, or the heteroaryl group is independently substituted by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, and nitro groups. Or, heteroarylamino or heteroarylamino, wherein the heteroaryl group is independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or diarylamino or diarylamino, wherein each heteroaryl group is independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy The phenyl group is substituted with a group selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or diphenylamino, wherein each phenyl group is independently substituted with a group selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or diphenylamino, wherein each phenyl group is independently substituted with a group selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or diphenylamino, wherein each phenyl group is independently substituted with a group selected from (C1-C3)-fluoro ... The phenyl group is substituted with a group selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or benzyloxy and phenyloxy, wherein the corresponding phenyl group is optionally independently substituted with 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, and ; R 21 For (C1-C 10 )-alkyl, (C3-C 10 )-Alkenyl, (C3-C 10 )-Alkyne group, (C1-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C2-C 10(C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenoxy-(C1-C5)-alkyl, (C3-C5)-alkynoxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)-alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-aminoalkyl, (C1-C5)-alkylamino-(C1-C5)-alkyl, (C2-C8)-dialkylamino-(C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C2-C8)-alkyl-dialkylamino-(C1-C5)-alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkyl-dialkylamino-(C1-C5)-alkyl, (C1-C5)- ... (C1-C5)-alkyleneaminooxy-(C1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl-(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkyl, N-(C1-C5)-alkylcarbonyl-N-(C1-C5)-alkylamino(C1-C5)-alkyl, (C3-C6)-trialkylsilyl-(C1-C5)-alkyl, phenyl -(C1-C5-alkyl, wherein the phenyl group is optionally and independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is optionally and independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkyl ... or heteroaryl-(C1-C5)-alkyl, wherein the phenyl group is optionally and independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, fluorine, chlorine, chloroalkyl, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, or heteroaryl-(C1-C5)-alkyl, or heteroaryl-(C1-C5)-alkyl, or heteroaryl-(C1-C5)-alkyl, or heteroaryl-(C1-C5)-alkyl The phenyl group is substituted with a group selected from (C1-C3)-alkoxy, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or phenoxy-(C1-C5)-alkyl, wherein the phenyl group is optionally independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkoxy, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryloxy-(C1-C5)-alkyl.The heteroaryl group is optionally and independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro groups, or the phenyl or phenyl group is optionally and independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, or phenyl groups. The phenyl group is substituted with a group selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro groups, or the phenyl-C(=O) group is optionally also independently substituted with a group selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro groups.
[0009] Surprisingly, it has been found that although the above-described herbicide structure exhibits significantly stronger weed-controlling activity than other herbicides, a high level of protection can still be achieved using the safener of the present invention. In this respect, the herbicide structure of the present invention is highly efficient, overcomes the resistance of certain weeds, and is safe for use on crop plants.
[0010] Regarding the compounds of the present invention, the terms used above and below will be explained. These terms are familiar to those skilled in the art and, in particular, have the definitions set forth below: When the above variable “W” or “Z” represents a connecting bond, it means that in the general formula (II) or derivative formula (II-1), the structural element Q is directly connected to the carbon atom, and the carbon atom is connected to Q through “W” or “Z”.
[0011] Regarding the nomenclature of chemical groups, the connection to the skeleton or the rest of the molecule is typically made by linking the chemical group through the last mentioned structural element. For example, in the case of (C2-C8)-olefin, it is linked by an oxygen atom, while in the case of heterocyclic-(C1-C8)-alkyl or (C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C 6) -Alkyl groups are all linked by the carbon atom of the alkyl group in their respective cases.
[0012] For connections to the rest of the molecule marked with "-", the connection is not through the last mentioned structural unit, but through the structural motif immediately adjacent to the connecting bond symbol "-". For example, in the case of -(CO)(C1-C6)-alkoxy-(C1-C6)-alkyl, the connection is achieved through a carbonyl group instead of (C1-C6)-alkyl, hence the use of the hyphen "-".
[0013] According to the present invention, "alkylthio"—either alone or as part of a chemical group—refers to a straight-chain or branched S-alkyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, for example (C1-C6). 10 (C1-C6)- or (C1-C4)-alkylthio, such as (but not limited to) (C1-C6)-alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-dimethylbutyrothio, 1,2-dimethylbutyrothio, 1,3-dimethylbutyrothio, 2,2-dimethylbutyrothio, 2,3-dimethylbutyrothio, 3,3-dimethylbutyrothio, 1-ethylbutyrothio, 2-ethylbutyrothio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.
[0014] "Alkoxy" refers to an alkyl group linked by an oxygen atom, such as (but not limited to) (C1-C6)-alkoxy, including methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, and hexoxy. 1-Methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy. Alkenyloxy groups represent alkenyl groups linked by oxygen atoms, and alkynyloxy groups represent alkynyl groups linked by oxygen atoms, for example (C2-C...). 10)-, (C2-C6)- or (C2-C4)-olefins and (C3-C 10 )-, (C3-C6)- or (C3-C4)-acetyloxy.
[0015] According to the present invention, unless otherwise defined, "alkyl carbonyl" (alkyl-C(=O)-) means an alkyl group bonded to the skeleton by -C(=O)-, for example (C1-C... 10 (C1-C6)- or (C1-C4)-alkylcarbonyl. The number of carbon atoms here is related to the alkyl group in the alkylcarbonyl group.
[0016] Unless otherwise defined, "alkoxycarbonyl (alkyl-OC(=O)-)": an alkyl group bonded to the skeleton by -OC(=O)-, such as (C1-C 10 (C1-C6)- or (C1-C4)-alkoxycarbonyl. The number of carbon atoms here is related to the alkyl group in the alkoxycarbonyl group. Similarly, according to the present invention, unless otherwise defined, "alkenoxycarbonyl" and "alkynoxycarbonyl" refer to alkenyl and alkynyl groups bonded to the skeleton by -OC (=O)-, such as (C2-C4)-, respectively. 10 )-, (C2-C6)- or (C2-C4)-olefin carbonyl and (C3-C 10 (C3-C6)- or (C3-C4)-alkynyloxycarbonyl. The number of carbon atoms here refers to the number of carbon atoms in the alkenyl or alkynyl group in the alkenyloxycarbonyl or alkynyloxycarbonyl group.
[0017] According to the present invention, unless otherwise defined, the term "alkyl carbonyloxy" (alkyl-C(=O)-O-) refers to an alkyl group bonded to the skeleton via the oxygen of the carbonyloxy group (C(=O)-O), for example (C1-C1-C1-O-). 10 (C1-C6)- or (C1-C4)-alkylcarbonyloxy groups. The number of carbon atoms here is related to the alkyl group in the alkylcarbonyloxy group.
[0018] In abbreviated form such as C(O)R 13 C(O)OR 13 OC(O)NR 11 R 12 or C(O)NR 11 R 12 In the example, the abbreviation O shown in parentheses represents an oxygen atom connected to an adjacent carbon atom via a double bond.
[0019] In abbreviated form, such as OC(S)OR 13 OC(S)SR 14 OC(S)NR 11 R 12In the brackets, the abbreviated form S represents a sulfur atom connected to an adjacent carbon atom via a double bond.
[0020] The term "aryl" refers to an optionally substituted monocyclic, bicyclic, or polycyclic aromatic system, preferably having 6 to 14, especially 6 to 10, cyclic carbon atoms, such as phenyl, naphthyl, anthracene, phenanthryl, etc., with phenyl being the most preferred.
[0021] The term "optionally substituted aryl" also includes polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, and biphenyl, wherein the bonding site is on an aromatic system. In systematic terminology, "aryl" is often also covered by the term "optionally substituted phenyl." Preferred aryl substituents herein are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclic, heterocyclic alkyl, alkoxyalkyl, alkoxythio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, dialkylaminoalkoxy, tri[alkyl]silyl, di[alkyl]arylsilyl, di[alkyl]alkenyl, di[alkyl]silyl [alkyl]alkylsilyl, tri[alkyl]silylynyl, arylynyl, heteroarylynyl, alkylynyl, cycloalkylynyl, haloalkylynyl, heterocyclic -N-alkoxy, nitro, cyano, amino, alkylamino, dialkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, dialkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.
[0022] The heterocyclic group (heterocyclic group) comprises at least one heterocycle (= carbocyclic ring, wherein at least one carbon atom is substituted with a heteroatom, preferably N, O, S, or P heteroatom), which may be saturated, unsaturated, partially saturated, or heteroaromatic and may be unsubstituted or substituted, in which case the bonding site is located on a ring atom. If the heterocyclic group or heterocycle is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclic groups, polycyclic systems are also included, such as 8-azabicyclo[3.2.1]octyl, 8-azabicyclo[2.2.2]octyl, or 1-azabicyclo[2.2.1]heptyl. Optionally substituted heterocyclic groups also include spirocyclic systems, such as 1-oxa-5-azaspiro[2.3]hexyl. Unless otherwise defined, heterocycles preferably contain 3 to 9 ring atoms, particularly 3 to 6 ring atoms, and may contain one or more, preferably 1 to 4, particularly 1, 2 or 3 heteroatoms, preferably selected from N, O and S, but there should not be two oxygen atoms directly adjacent to each other, for example having one heteroatom selected from N, O and S: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrolidin-2- or -3-yl, 2,3-dihydro-1H-pyrrolidin-1- or -2- or -3- or -4- or 5-yl 2,5-Dihydro-1H-pyrrole-1- or -2- or -3-yl, 1- or 2- or 3- or 4-piperidinyl, 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5- or 6-yl, 1,2,3,6-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,2,3,4-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,4-dihydropyridine-1- or 2- or 3- or 4-yl, 2,3- Dihydropyridin-2- or -3- or -4- or -5- or -6-yl, 2,5-dihydropyridin-2- or -3- or -4- or -5- or -6-yl, 1- or 2- or 3- or 4-azacycloheptyl, 2,3,4,5-tetrahydro-1H-azacycloheptene-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydro-1H-azacycloheptene-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro- 1H-azacyclohepten-1- or -2- or -3- or -4-yl, 3,4,5,6-tetrahydro-2H-azacyclohepten-2- or -3- or -4- or -5- or -6- or -7-yl, 4,5-dihydro-1H-azacyclohepten-1- or -2- or -3- or -4-yl, 2,5-dihydro-1H-azacyclohepten-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,7-dihydro-1H-azacyclohepten-1- or -2- or -3- or -4-yl, 2,3-Dihydro-1H-azacyclohepten-1-or-2-or-3-or-4-or-5-or-6-or-7-yl, 3,4-Dihydro-2H-azacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 3,6-Dihydro-2H-azacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 5,6-Dihydro-2H-azacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 4,5-Dihydro-3H-azacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 1H-azacyclohepten-1-or-2-or-3-or-4-or-7-yl 5- or -6- or -7-yl, 2H-azacyclohepten-2- or -3- or -4- or -5- or -6- or -7-yl, 3H-azacyclohepten-2- or -3- or -4- or -5- or -6- or -7-yl, 4H-azacyclohepten-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-oxacyclopentyl (=2- or 3-tetrahydrofuranyl), 2,3-dihydrofuran-2- or -3- or -4- or -5-yl, 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxacyclohexyl (=2- or 3- or 4-tetrahydropyranyl), 3,4-dihydro-2H-pyran-2- or -3-yl -or-4-or-5-or-6-yl, 3,6-dihydro-2H-pyran-2-or-3-or-4-or-5-or-6-yl, 2H-pyran-2-or-3-or-4-or-5-or-6-yl, 4H-pyran-2-or-3-or-4-yl, 2-or-3-or-4-oxetane, 2,3,4,5-tetrahydrooxetane-heptene-2-or-3-or-4-or-5-or-6-or-7-yl, 2,3,4,7-tetrahydrooxetane-heptene-2-or-3-or-4-or-5-or-6-or-7-yl, 2,3-dihydrooxetane Hepten-2- or -3- or -4- or -5- or -6- or -7-yl, 4,5-dihydrooxetrazine-2- or -3- or -4-yl, 2,5-dihydrooxetrazine-2- or -3- or -4- or -5- or -6- or -7-yl, oxetrazine-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-tetrahydrothiophene, 2,3-dihydrothiophene-2- or -3- or -4- or -5-yl, 2,5-dihydrothiophene-2- or -3-yl, tetrahydro-2H-thiaran-2- or -3- or -4-yl, 3,4-dihydro-2H-thiaran-2- or -3- or -4- or -5- or -6-yl, 3,6-Dihydro-2H-thiaran-2- or -3 or -4 or -5 or -6-yl, 2H-thiaran-2- or -3 or -4 or -5 or -6-yl, 4H-thiaran-2- or -3 or -4-yl. Preferred 3- and 4-membered heterocycles are, for example, 1- or 2-azacyclopropyl, oxacyclopropyl, thiocyclopropyl, 1- or 2- or 3-azacyclobutyl, 2- or 3-oxacyclobutyl, 2- or 3-thiocyclobutyl, 1,3-dioxacyclobutyl-2-yl. Other examples of "heterocyclic groups" are partially or fully hydrogenated heterocyclic groups having two heteroatoms selected from N, O, and S, such as 1- or 2- or 3- or 4-pyrazolyl groups, 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl groups, 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl groups, 2,3-dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl groups, 1- or 2- or 3- or 4-imidazolyl groups, 2,3-dihydro-1H-imidazolyl-1- or 2- or 3- or 4-yl groups, 2,5-dihydro-1H-imidazolyl-1- or 2- or 4- or 5-yl groups, 4, 5-Dihydro-1H-imidazol-1-or-2-or-4-or-5-yl, hexahydropyridazine-1-or-2-or-3-or-4-yl, 1,2,3,4-tetrahydropyridazine-1-or-2-or-3-or-4-or-5-or-6-yl, 1,2,3,6-tetrahydropyridazine-1-or-2-or-3-or-4-or-5-or-6-yl, 1,4,5,6-tetrahydropyridazine-1-or-3-or-4-or-5-or-6-yl, 3,4,5,6-tetrahydropyridazine-3-or-4-or-5-yl, 4,5-dihydropyridazine-3-or-4-yl, 3,4-dihydropyridazine-3-or-4-or-5-or-6-yl, 3,6 -Dihydropyridazine-3- or 4-yl, 1,6-Dihydropyridazine-1- or 3- or 4- or 5- or 6-yl, hexahydropyrimidine-1- or 2- or 3- or 4-yl, 1,4,5,6-Tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl, 1,2,5,6-Tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl, 1,2,3,4-Tetrahydropyrimidine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,6-Dihydropyrimidine-1- or 2- or 4- or 5- or 6-yl, 1,2-Dihydropyrimidine-1- or 2- or 4- or 5- or 6-yl, 2,5-Dihydropyrimidine-2- or 4- or 5-yl, 4,5-dihydropyrimidin-4- or 5- or 6-yl, 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl, 1- or 2- or 3-piperazinyl, 1,2,3,6-tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl, 1,2-dihydropyrazine-1- or 2- or 3- or 5- or 6-yl, 1,4-dihydropyrazine-1- or 2- or 3-yl, 2,3-dihydropyrazine-2- or 3- or 5- or 6-yl, 2,5-dihydropyrazine-2- or 3-yl, 1,3-Dioxolane-2- or 4- or 5-yl, 1,3-dioxacyclopenten-2- or 4-yl, 1,3-dioxane-2- or 4- or 5-yl, 4H-1,3-dioxin-2- or 4- or 5- or 6-yl, 1,4-dioxane-2- or 3- or 5- or 6-yl, 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl -yl, 1,4-dioxin-2- or 3-yl, 1,2-dithiacyclopentan-3- or 4-yl, 3H-1,2-dithiacyclopenten-3- or 4- or 5-yl, 1,3-dithiacyclopenten-2- or 4-yl, 1,3-dithiacyclopenten-2- or 4-yl, 1,2-dithiaran-3- or 4-yl, 3,4-dihydro-1,2-dithiain-3 -or 4-or 5-or 6-yl, 3,6-dihydro-1,2-dithiain-3-or 4-yl, 1,2-dithiain-3-or 4-yl, 1,3-dithiane-2-or 4-or 5-yl, 4H-1,3-dithiain-2-or 4-or 5-or 6-yl, isoxazolidine-2-or 3-or 4-or 5-yl, 2,3-dihydroisoxazol-2-or 3-yl or 4- or 5-yl, 2,5-dihydroisoxazole-2- or 3- or 4- or 5-yl, 4,5-dihydroisoxazole-3- or 4- or 5-yl, 1,3-oxazolidine-2- or 3- or 4- or 5-yl, 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl, 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl, 4, 5-Dihydro-1,3-oxazol-2-, 4-, or 5-yl, 1,2-oxazhexane-2-, 3-, 4-, 5-, or 6-yl, 3,4-dihydro-2H-1,2-oxazine-2-, 3-, 4-, 5-, or 6-yl, 3,6-dihydro-2H-1,2-oxazine-2-, 3-, 4-, 5-, or 6-yl, 5,6-dihydro-2H -1,2-oxazine-2-or-3-or-4-or-5-or-6-yl, 5,6-dihydro-4H-1,2-oxazine-3-or-4-or-5-or-6-yl, 2H-1,2-oxazine-2-or-3-or-4-or-5-or-6-yl, 6H-1,2-oxazine-3-or-4-or-5-or-6-yl, 4H-1,2-oxazine-3-or-4-or-5-or-6-yl 1,3-oxazhexane-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,3-oxazine-2- or 4- or 5- or 6-yl 5,6-Dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl, 2H-1,3-oxazine-2- or 4- or 5- or 6-yl, 6H-1,3-oxazine-2- or 4- or 5- or 6-yl, 4H-1,3-oxazine-2- or 4- or 5- or 6-yl, morpholin-2- or 3- or 4-yl, 3,4-dihydro-2H-1,4-Oxazin-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl, 2H-1,4-oxazin-2- or 3- or 5- or 6-yl, 4H-1,4-oxazin-2- or 3-yl, 1,2-oxazyrazine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3, 4,5-Tetrahydro-1,2-oxazacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 2,3,4,7-Tetrahydro-1,2-oxazacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 2,3,6,7-Tetrahydro-1,2-oxazacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 2,5,6 7-Tetrahydro-1,2-oxazacyclohepten-2,3-,4-,5-,6-,7-tetrahydro-1,2-oxazacyclohepten-3,4-,5-,6-,7-tetrahydro-1,2-oxazacyclohepten-3,3-dihydro-1,2-oxazacyclohepten-2,3-,4-,5-,6-,7 ...5-,4-,5-,6-,7-dihydro-1,2-oxazacyclohepten-2,3-,4-,5- Cyclohepten-2- or 3- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,2-oxazacyclohepten-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1,2-oxazacyclohepten-3- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,2-oxazacyclohepten-3- or 4- or 5- or 6- or 7-yl 6,7-dihydro-1,2-oxazetene-3- or 4- or 5- or 6- or 7-yl, 1,2-oxazetene-3- or 4- or 5- or 6- or 7-yl, 1,3-oxazetene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,5-tetrahydro-1,3-oxazetene-2- or 3- or 4- or 5-yl -or 6-or 7-yl, 2,3,4,7-tetrahydro-1,3-oxazetene-2-or 3-or 4-or 5-or 6-or 7-yl, 2,3,6,7-tetrahydro-1,3-oxazetene-2-or 3-or 4-or 5-or 6-or 7-yl, 2,5,6,7-tetrahydro-1,3-oxazetene-2-or 4-or 5-or 6-or 7-yl, 4,5,6,7-tetrahydro-1,3-oxazetene-2- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-1,3-oxazetene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5-dihydro-1,3-oxazetene-2- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,3-oxazetene-2- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,3-oxazetene Aza-hepten-2- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1,3-oxaza-hepten-2- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,3-oxaza-hepten-2- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1,3-oxaza-hepten-2- or 4- or 5- or 6- or 7-yl, 1,3-Oxazolidinyl-2- or 4- or 5- or 6- or 7-yl, 1,4-Oxazolidinyl-2- or 3- or 5- or 6- or 7-yl, 2,3,4,5-Tetrahydro-1,4-Oxazolidinyl-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-Tetrahydro-1,4-Oxazolidinyl-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-Tetrahydro-1,4-Oxazolidinyl-2- or 3- or 5- or 6- or 7-yl, 2,5,6,7-Tetrahydro-1,4-Oxazolidinyl-2- or 3- or 5- or 6- or 7-yl, 4,5,6,7-Tetrahydro- 1,4-Oxazolidinyl-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-1,4-Oxazolidinyl-2- or 3- or 5- or 6- or 7-yl, 2,5-dihydro-1,4-Oxazolidinyl-2- or 3- or 5- or 6- or 7-yl, 2,7-dihydro-1,4-Oxazolidinyl-2- or 3- or 5- or 6- or 7-yl, 4,5-dihydro-1,4-Oxazolidinyl-2- or 3- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,4-Oxazolidinyl-2- or 3- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1,4-Oxazolidinyl-6 -2- or 3- or 5- or 6- or 7-yl, 1,4-oxazetene-2- or 3- or 5- or 6- or 7-yl, isothiazolidine-2- or 3- or 4- or 5-yl, 2,3-dihydroisothiazolidine-2- or 3- or 4- or 5-yl, 2,5-dihydroisothiazolidine-2- or 3- or 4- or 5-yl, 4,5-dihydroisothiazolidine-3- or 4- or 5-yl, 1,3-thiazolidine-2- or 3- or 4- or 5-yl, 2,3-dihydro-1,3-thiazolidine-2- or 3- or 4- or 5-yl, 2,5-dihydro-1,3-thiazolidine-2- or 4- or 5-yl, 4,5-dihydro-1,3-thiazolidine-2- or 4- or 5-yl - 1,3-thiazinyl-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,3-thiazinyl-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,3-thiazinyl-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,3-thiazinyl-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,3-thiazinyl-2- or 4- or 5- or 6-yl, 2H-1,3-thiazinyl-2- or 4- or 5- or 6-yl, 6H-1,3-thiazinyl-2- or 4- or 5- or 6-yl, 4H-1,3-thiazinyl-2- or 4- or 5- or 6-yl. Other examples of "heterocyclic groups" are partially or fully hydrogenated heterocyclic groups having three heteroatoms selected from N, O, and S, such as 1,4,2-dioxazolidine-2-, 3-, or 5-yl, 1,4,2-dioxazol-3-, or 5-yl, 1,4,2-dioxazinidine-2-, 3-, 5-, or 6-yl, 5,6-dihydro-1,4,2-Dioxazine-3-or 5-or 6-yl, 1,4,2-Dioxazine-3-or 5-or 6-yl, 1,4,2-Dioxazine-2-or 3-or 5-or 6-or 7-yl, 6,7-Dihydro-5H-1,4,2-Dioxazine-3-or 5-or 6-or 7-yl, 2,3-Dihydro-7H-1,4,2-Dioxazine-2-or 3-or 5-or 6-or 7-yl, 2,3-Dihydro-5H-1,4,2-Dioxazine-2-or 3-or 5-or 6-or 7-yl, 5H-1,4,2-Dioxazine-3-or 5-or 6-or 7-yl, 7H-1,4,2-Dioxazine-3-or 5-or 6-or 7-yl. The following also lists structural examples of heterocyclic rings that may be further substituted: The heterocycles listed above are preferably substituted with the following groups: for example, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclic, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trialkylsilylalkynyl, nitro, amino, cyano. Halogenated alkoxy, halogenated alkylthio, alkylthio, hydrogen thio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclic alkoxy, heterocyclic alkylthio, heterocyclic thio, heteroaryloxy, dialkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.
[0023] When the basic structure is replaced by "one or more groups" selected from a list of groups or a generally defined group of groups, in each case this includes being replaced by multiple identical and / or structurally different groups simultaneously.
[0024] In the case of partially or fully saturated nitrogen heterocycles, this can be attached to the rest of the molecule via carbon or nitrogen.
[0025] Suitable substituents for the substituted heterocyclic group are those further specified below, as well as oxo and thio groups. The oxo group, then, as a substituent on the ring carbon atom, is, for example, a carbonyl group in the heterocycle. Therefore, lactones and lactams are preferably also included. The oxo group can also appear on the ring heteroatom, which can exist in different oxidation states, for example in the cases of N and S, and in this case, divalent -N(O)-, S(O)- (also simply SO), and -S(O)2- (also simply SO2) groups are formed in the heterocycle. In the cases of -N(O)- and -S(O)- groups, both enantiomers are included in each case.
[0026] According to the present invention, the term "heteroaryl" refers to a heteroaromatic compound, that is, a fully unsaturated aromatic heterocyclic compound, preferably having 1 to 4, more preferably 1 or 2 identical or different heteroatoms, preferably O, S or N, 5 to 7-membered rings. The heteroaryl groups of the present invention are, for example, 1H-pyrrolo-1-yl, 1H-pyrrolo-2-yl, 1H-pyrrolo-3-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, 1H-imidazol-1-yl, 1H-imidazol-2-yl, 1H-imidazol-4-yl, 1H-imidazol-5-yl, 1H-pyrazole-1-yl, 1H-pyrazole-3-yl, 1H-pyrazole-4-yl, 1H-pyrazole-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H -1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, azacycloheptenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3 -yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol- 5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, oxeheptenel, thioheptenel, 1,2,4-triazolonel and 1,2,4-diazaheptenyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The heteroaryl groups of the present invention can also be substituted with one or more identical or different groups. If two adjacent carbon atoms are part of another aromatic ring, the system is a fused heteroaromatic system, such as benzofused or polycyclic heteroaromatic compounds.Preferred examples are quinolines (e.g., quinoline-2-yl, quinoline-3-yl, quinoline-4-yl, quinoline-5-yl, quinoline-6-yl, quinoline-7-yl, quinoline-8-yl), isoquinolines (e.g., isoquinoline-1-yl, isoquinoline-3-yl, isoquinoline-4-yl, isoquinoline-5-yl, isoquinoline-6-yl, isoquinoline-7-yl, isoquinoline-8-yl), quinoxaline, quinazolin, zoline, 1,5-naphthoidine, 1,6-naphthoidine, 1,7-naphthoidine, 1,8-naphthoidine, 2,6-naphthoidine, 2,7-naphthoidine, phthalazine, pyridopyrazine, pyridopyrimidine, pyridopyridazine, pteridine, pyrimidine. Examples of heteroaryl groups also include 5- or 6-membered benzo[a]-fused rings selected from 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-Benzothiophene-5-yl, 1-Benzothiophene-6-yl, 1-Benzothiophene-7-yl, 1H-Indazole-1-yl, 1H-Indazole-3-yl, 1H-Indazole-4-yl, 1H-Indazole-5-yl, 1H-Indazole-6-yl, 1H-Indazole-7-yl, 2H-Indazole-2-yl, 2H-Indazole-3-yl, 2H-Indazole-4-yl, 2H-Indazole-5-yl, 2H-Indazole-6-yl, 2H-Indazole-7-yl, 2H-Isoindol-2-yl, 2H-Isoindol-1-yl, 2H-Isoindol-3-yl, 2H-Isoindol-2-yl 4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl, 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1, 3-Benzothiazol-4-yl, 1,3-Benzothiazol-5-yl, 1,3-Benzothiazol-6-yl, 1,3-Benzothiazol-7-yl, 1,2-Benzisoxazole-3-yl, 1,2-Benzisoxazole-4-yl, 1,2-Benzisoxazole-5-yl, 1,2-Benzisoxazole-6-yl, 1,2-Benzisoxazole-7-yl, 1,2-Benzisothiazol-3-yl, 1,2-Benzisothiazol-4-yl, 1,2-Benzisothiazol-5-yl, 1,2-Benzisothiazol-6-yl, 1,2-Benzisothiazol-7-yl.
[0027] The term "halogen" refers to, for example, fluorine, chlorine, bromine, or iodine. If this term is used with a group, then "halogen" refers to, for example, a fluorine, chlorine, bromine, or iodine atom.
[0028] According to the present invention, "alkyl" refers to a straight-chain or branched open-chain saturated hydrocarbon group, which is optionally monosubstituted or polysubstituted, and in the latter case is called "substituted alkyl". Preferred substituents are halogen atoms, alkoxy groups, haloalkoxy groups, cyano groups, alkylthio groups, haloalkylthio groups, amino groups, or nitro groups, with methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine, or iodine groups being particularly preferred. The prefix "di" also includes combinations of different alkyl groups, such as methyl (ethyl) or ethyl (methyl).
[0029] "Haloalkyl," "-alkenyl," and "-ynyl" refer to alkyl, alkenyl, and ynyl groups that are partially or wholly replaced by the same or different halogen atoms, respectively. Examples include monohaloalkyl groups such as CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, and CH2F; perhaloalkyl groups such as CCl3, CClF2, CFCl2, CF2CClF2, and CF2CClFCF3; and polyhaloalkyl groups such as CH2CHFCl, CF2CClFH, CF2CBrFH, and CH2CF3. The term "haloalkyl" also includes the term "fluoroalkyl." The term "perhaloalkyl" also includes the term "perfluoroalkyl."
[0030] "Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl; this applies accordingly to haloalkenyl and other halogen-substituted groups.
[0031] The term "(C1-C5)-alkyl" as used herein by way of example is an abbreviation for a straight-chain or branched alkyl group having 1 to 5 carbon atoms according to the stated carbon atom range, including, for example, methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, tert-butyl, 1-pentyl, 2-methylbut-1-yl, 3-methylbut-1-yl, and 2,2-dimethylpropyl-1-yl groups. General alkyl groups having a larger specified carbon atom range, such as "(C1-C6)-alkyl", correspondingly also include straight-chain or branched alkyl groups having more carbon atoms, i.e., according to examples, also include alkyl groups having 5 and 6 carbon atoms.
[0032] Unless otherwise specified, in the case of hydrocarbon groups such as alkyl, alkenyl, and alkynyl groups, including hydrocarbon groups in complex groups, a lower carbon skeleton is preferred, for example, having 1 to 6 carbon atoms, or 2 to 6 carbon atoms in the case of unsaturated groups. Alkyl groups, including alkyl groups in complex groups such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, tert-butyl or 2-butyl, pentyl, hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl, heptyl such as n-heptyl, 1-methylhexyl, and 1,4-dimethylpentyl; alkenyl and alkynyl groups are defined as possible unsaturated groups corresponding to alkyl groups, wherein at least one double or triple bond is present. Groups having one double or triple bond are preferred.
[0033] The term "alkenyl" also specifically includes straight-chain or branched open-chain hydrocarbon groups having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, as well as allenyl or cumulenyl groups having one or more cumulative double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-penttrienyl. Alkenyl means, for example, vinyl, which may optionally be substituted with other alkyl groups, such as (but not limited to) (C2-C6)-alkenyl, such as vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3- Methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl 4-Methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2 2-Dimethyl-3-butenyl, 2,3-Dimethyl-1-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1-butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1-butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1,1,2-Trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-Ethyl-2-methyl-1-propenyl and 1-Ethyl-2-methyl-2-propenyl.
[0034] The term "alkynyl" also specifically includes straight-chain or branched open-chain hydrocarbon groups that have more than one triple bond, or have one or more triple bonds and one or more double bonds, such as 1,3-buttrienyl or 3-pent-1-yn-1-yl. (C2-C6)-alkynyl groups, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3- -Pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.
[0035] The term "cycloalkyl" refers to a carbocyclic saturated ring system, preferably having 3 to 8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, which is optionally further substituted, preferably substituted with the following groups: hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, dialkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl groups, the cyclic system having substituents also includes substituents having a double bond on the cycloalkyl group, such as alkylene groups, like methylene. In the case of optionally substituted cycloalkyl groups, polycyclic aliphatic systems are also included, such as bicyclo[1.1.0]but-1-yl, bicyclo[1.1.0]but-2-yl, bicyclo[2.1.0]pent-1-yl, bicyclo[1.1.1]pent-1-yl, bicyclo[2.1.0]pent-2-yl, bicyclo[2.1.0]pent-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]oct-2-yl, bicyclo[3.2.1]oct-2-yl, bicyclo[3.2.2]non-2-yl, adamantane-1-yl and adamantane-2-yl, as well as systems such as 1,1'-di(cyclopropyl)-1-yl and 1,1'-di(cyclopropyl)-2-yl. The term "(C3-C7)-cycloalkyl" is an abbreviation for cycloalkyl groups having 3 to 7 carbon atoms within a specified range of carbon atoms.
[0036] "Cycloalkenyl" preferably refers to a carbocyclic, non-aromatic, partially unsaturated ring system having 4-8 carbon atoms, such as 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl, or 1,4-cyclohexadienyl, and also includes substituents having a double bond on the cycloalkenyl group, such as alkylene groups like methylene. In the case of optionally substituted cycloalkenyl groups, the description of substituted cycloalkyl groups applies accordingly.
[0037] The term "alkylidene" is also used for (C1-C) 10 The alkylene group (=)- is a straight-chain or branched open-chain hydrocarbon group linked by a double bond. The possible bonding sites for alkylene groups are naturally only those positions on the basic structure where two hydrogen atoms can be replaced by a double bond; the group is, for example, =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5, or =C(C2H5)-C2H5. Cycloalkylene groups (=)- are carbocyclic groups linked by a double bond.
[0038] The term "alkylene", for example in the form of (C1-C8)-alkylene, refers to a straight-chain or branched open-chain hydrocarbon group that is connected to other groups at two positions.
[0039] "Alkoxyalkyl" refers to an alkoxy group bonded by an alkyl group, and "alkoxyalkyl" refers to an alkoxyalkyl group bonded by an oxygen atom, such as (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropoxy.
[0040] "Arylalkyl" refers to an aryl group bonded by an alkyl group, "heteroarylalkyl" refers to a heteroaryl group bonded by an alkyl group, and "heterocyclicalkyl" refers to a heterocyclic group bonded by an alkyl group.
[0041] "Cycloalkylalkyl" refers to a cycloalkyl group bonded by an alkyl group, such as (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropylethyl-1-yl, 2-cyclopropylethyl-1-yl, 1-cyclopropylpropyl-1-yl, and 3-cyclopropylpropyl-1-yl.
[0042] "Arylalkenyl" refers to an aryl group linked by an alkenyl group, "heteroarylalkenyl" refers to a heteroaryl group linked by an alkenyl group, and "heterocyclic alkenyl" refers to a heterocyclic group linked by an alkenyl group.
[0043] "Aromaticynyl" indicates an aryl group linked by an alkynyl group, "Heteroaryynyl" indicates a heteroaryl group linked by an alkynyl group, and "Heterocyclicynyl" indicates a heterocyclic group linked by an alkynyl group.
[0044] According to the present invention, the “haloalkylthio group”—either itself or as a component of a chemical group—is a straight-chain or branched S-haloalkyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (C1-C8)-, (C1-C6)- or (C1-C4)-haloalkylthio groups, such as (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroethyl-1-ylthio, 2,2,2-difluoroethyl-1-ylthio, 3,3,3-propyl-1-ylthio.
[0045] "Halocycloalkyl" and "halocycloalkenyl" respectively refer to cycloalkyl or cycloalkenyl groups that are partially or completely substituted with the same or different halogen atoms (e.g., F, Cl, and Br) or haloalkyl groups (e.g., trifluoromethyl or difluoromethyl), such as 1-fluorocyclopropyl-1-yl, 2-fluorocyclopropyl-1-yl, 2,2-difluorocyclopropyl-1-yl, 1-fluorocyclobutyl-1-yl, 1-trifluoromethylcyclopropyl-1-yl, 2-trifluoromethylcyclopropyl-1-yl, 1-chlorocyclopropyl-1-yl, 2-chlorocyclopropyl-1-yl, 2,2-dichlorocyclopropyl-1-yl, and 3,3-difluorocyclobutyl.
[0046] Only neutral compounds are mentioned below, and therefore all listed forms of existence are covered, unless the specific form of the active ingredient is important in a particular context, such as in the bioefficacy examples in the table below.
[0047] The herbicide / safety agent combination of the present invention may contain other components, such as other active ingredients for combating pests (e.g., harmful plants, animals that damage plants, or fungi that damage plants), particularly active ingredients selected from herbicides, fungicides, insecticides, acaricides, nematicides and miticides and related substances, or other types of active ingredients for crop protection (e.g., resistance inducers), crop plant protection active ingredients (safeties, antidotes other than component (A), plant growth regulators, and / or additives and / or formulation adjuvants commonly used in crop protection), in addition to the herbicides mentioned in section B. These components may be formulated together (ready-to-use formulations) and used as is, or they may be formulated separately and then used together, for example, in tank mixing or sequential application.
[0048] When a single safener of formula (I) appears as component (A), it is also referred to hereinafter as compound (A), active ingredient (A), component (A), or safener (A). Correspondingly, when a single active herbicidal ingredient appears as component (B), it is also referred to hereinafter as compound (B), active ingredient (B), component (B), herbicide (B), or compound of formula (II).
[0049] The advantageous feature of the combination of the safener (A) and herbicide (B) of the present invention is that the safener (A) and herbicide (B) are compatible with each other, meaning that they can be used together without significant chemical incompatibility between the safener (A) and / or herbicide (B) that would cause the safener (A) or herbicide (B) to be destroyed.
[0050] This good compatibility also extends to the biological properties of the active ingredients when used in combination. For example, no antagonistic effects are typically observed when using the herbicide / safener combination of the present invention to control harmful plants.
[0051] In compounds of the safener (A) of formula (I) and compounds of the herbicide (B) of formula (II), and in all the chemical formulas below, the following definitions apply: Depending on the nature of the substituents and their connection, compounds of formula (I) or (II) can exist as stereoisomers. For example, enantiomers and diastereomers may occur if one or more asymmetrically substituted carbon and / or sulfur atoms are present. Stereoisomers can be obtained from the mixtures obtained in the preparation by conventional separation methods (e.g., chromatographic separation). Similarly, stereoisomers can be selectively prepared by using stereoselective reactions with the aid of optically active starting materials and / or auxiliaries.
[0052] The present invention also relates to all stereoisomers and mixtures thereof covered but not specifically defined by formula (I) or (II). However, for simplicity, compounds of formula (I) or (II) will always be referred to below, even though this means not only pure compounds, but also, where appropriate, mixtures of isomers in different proportions.
[0053] Based on the properties of the substituents defined above, compounds of formula (I) or (II) possess acidic properties and can form salts with inorganic or organic bases or with metal ions, and, if suitable, can also form internal salts or adducts. If compounds of formula (I) or (II) contain a hydroxyl, carboxyl, or other acidic group, these compounds can react with a base to form a salt. Suitable bases include, for example, hydroxides, carbonates, and bicarbonates of alkali metals and alkaline earth metals (especially sodium, potassium, magnesium, and calcium), and ammonia; primary, secondary, and tertiary amines having (C1-C4)-alkyl groups; monoalkylolamines, dialkylolamines, and trialkylolamines (C1-C4)-alkanols; choline and choline chloride; and organic amines such as trialkylamines, morpholine, piperidine, or pyridine. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, such as metal salts, especially alkali metal or alkaline earth metal salts, particularly sodium and potassium salts, or ammonium salts, salts of organic amines or quaternary ammonium salts, for example having the formula [NRR´R´´R´´´]. + The cation, wherein R to R''' are each independently an organic group, especially alkyl, aryl, aralkyl, or alkylaryl. Alkyl sulfonate salts and alkyl oxide sulfonate salts are also used, such as (C1-C4)-trialkyl sulfonate salts and (C1-C4)-trialkyl oxide sulfonate salts.
[0054] Specifically, G in the compound of formula (II) can be an agriculturally acceptable metal, such as copper, iron, lithium, sodium, potassium, magnesium or calcium (especially alkali metals or alkaline earth metals).
[0055] Compounds of formula (I) or (II) can be formed by adding a suitable inorganic or organic acid (e.g., mineral acids such as HCl, HBr, H₂SO₄, H₃PO₄, or HNO₃; or organic acids such as carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or sulfonic acid such as p-toluenesulfonic acid) to a basic group (e.g., amino, alkylamino, dialkylamino, piperidinyl, morpholinyl, or pyridinyl). These salts also contain the conjugate base of the acid in anionic form.
[0056] Suitable substituents in deprotonated form, such as sulfonic acids or carboxylic acids, can form internal salts with groups that can be protonated themselves (such as amino groups).
[0057] If a group is substituted by multiple groups, this means that the group is substituted by one or more substituents that are the same as or different from those mentioned.
[0058] The following is a description of the preferred, particularly preferred, and very particularly preferred definitions for each individual safener (A) and herbicide (B).
[0059] If a compound can form a tautomer whose structure is not formally covered by general formula (A) through hydrogen transfer, such tautomers are included in the definition of compounds of general formula (A) of the present invention, unless a specific tautomer is being considered. For example, many carbonyl compounds can exist simultaneously in the form of ketones and enols, both of which are included in the definition of compounds of general formula (A).
[0060] Compounds of general formula (I) may exist as stereoisomers depending on the nature of the substituents and their connection methods. Possible stereoisomers defined by their specific three-dimensional form, such as enantiomers, diastereomers, Z- and E-isomers, are all covered by general formula (I). For example, diastereomers (Z- and E-isomers) may occur if one or more alkenyl groups are present. For example, enantiomers and diastereomers may occur if one or more asymmetric carbon atoms are present. Stereoisomers can be obtained from mixtures obtained in the preparation by conventional separation methods. Chromatographic separation can be performed on an analytical scale to determine enantiomer or diastereomer excess, or on a preparative scale to prepare test samples for bioassays. Similarly, stereoisomers can be selectively prepared by stereoselective reactions using optically active starting materials and / or auxiliaries. Therefore, the present invention also relates to all stereoisomers covered by general formula (I) but not shown in a specific stereoform, and mixtures thereof.
[0061] If the compound is obtained in solid form, it can also be purified by recrystallization or refining. If a single compound of general formula (I) cannot be obtained satisfactorily by the routes described below, they can be prepared by derivatization of other compounds of general formula (I).
[0062] Suitable separation, purification, and methods for separating stereoisomers of compounds of general formula (I) are methods commonly known to those skilled in the art in similar cases, such as by physical methods like crystallization, chromatography, particularly column chromatography and HPLC (high-performance liquid chromatography), distillation (optionally under reduced pressure), extraction, and other methods. Any remaining mixture can usually be separated by chromatographic methods, such as on a chiral solid phase. Methods suitable for preparative or industrial-scale applications include crystallization, such as the crystallization of diastereomeric salts obtained from diastereomeric mixtures using optically active acids (if appropriate, provided an acidic group is present) and optically active bases.
[0063] In one embodiment of the invention, the herbicide / safety agent combination of the invention and at least one component (B) as defined above preferably comprise a component of general formula (I) (safety agent (A)) or an agriculturally chemically acceptable salt thereof, as detailed in Table 1.
[0064] Table 1: IUPAC names and structural formulas of preferred compounds of formula (I) (safety agent (A)) The compound of formula (I) is known from international application (application number PCT / EP2020 / 083167(WO2021 / 105101)) and can be prepared by the method described therein.
[0065] In the context of this invention, particularly preferred safety agents (A) are compounds numbered A1, A3, A5, A7 and A9 according to Table 1 above.
[0066] Compounds of formula (II) are known from international applications WO2021009229, WO2015197468, WO202109048, WO2021009232, WO2019158666, WO2020169648, WO2020165233, WO2020165102, WO2020074489, WO2019175117, WO2019170745 and WO202118826, and can be prepared by the methods described therein.
[0067] Preferred herbicides are those of general formula (II), wherein Q is a Q-1 group. R 1 It is a methyl, 1-propynyl, or a six-membered heteroaromatic ring containing one or two nitrogen atoms, wherein the heteroaromatic ring can be converted into an R-membered ring. 9 Group substitution, R 2 It is chlorine, methoxy, methyl, or ethyl. R 3 It is chlorine, methyl, or ethyl. W can be CH2, O, NH, or N-CH3. Y is O or NR 8 , Z stands for linker or CH2. n1 and n2 are independently 1 or 2, provided that n1 + n2 = 2, 3, or 4. R 8 It can be (C1-C4)-alkoxy, -C(O)(C1-C4)-alkyl, -C(O)-(C3-C6)-cycloalkyl, or -C(O)O(C1-C6)-alkyl. -S(O)2NHR 17N -S(O)(=NH)R 19N -C(O)C(O)R 20N , -C(O)C(R) 23N )=NOR 24N ; R 9 It is either cyano or halogen; R 17N It is methyl or ethyl; R 19N It is methyl or ethyl; R 20N Methyl, ethyl or -NHR 22N ; R 22N N is methyl or ethyl; R 23N It is methyl or ethyl; R 24N It is methyl or ethyl; G is hydrogen, a metal acceptable in agricultural chemistry, C(O)-R 14 or -C(O)-OR 15 , R 14 It is (C1-C6)-alkyl. R 15 It is (C1-C6)-alkyl.
[0068] Preferred herbicides are those of general formula (II), among which Q is a Q-2 group. R 1 It is 1-propynyl. R 2 It is chlorine, methoxy, methyl, or ethyl. R 3 It is chlorine, methyl, or ethyl. W can be CH2, O, NH, or N-CH3. Y is NR 8 , Z stands for linker or CH2. n1 is 2, R 8 It is (C1-C4)-alkoxy, -C(O)(C1-C4)-alkyl, -C(O)-(C3-C6)-cycloalkyl or -S(O)2C(R 11N )R 12N R 13N ; R 11N It is hydrogen; R 12N It is hydrogen; R 13N It is methyl; G is hydrogen, a metal acceptable in agricultural chemistry, C(O)-R 14 or -C(O)-OR 15 , R 14 It is (C1-C6)-alkyl. R 15 It is (C1-C6)-alkyl.
[0069] Preferred herbicides are those of general formula (II), wherein Q is the Q-3 group. R 1 It is 1-propynyl. R 2 It is chlorine, methoxy, methyl, or ethyl. R 3 It is chlorine, methyl, or ethyl. W can be CH2, O, NH, or N-CH3. Z stands for linker or CH2. R 1Q3 It is hydrogen or (C1-C6)-alkyl. R 2Q3 -(CH2) k -R 3Q3 , Where R 3Q3 Selected from -C(O)NR 5N R 6N -NR5N R 6N and -S(O)2NR 16N R 17N , And k is 0, or R 1Q3 and R 2Q3 Together for -(CH2) nq1 -C(R 4Q3 R 5Q3 -(CH2) nq2 -where nq1 and nq2 are independently 1 or 2, R 4Q3 It is hydrogen or (C1-C6)-alkyl. R 5Q3 Selected from -C(O)NR 5N R 6N -NR 5N R 6N and -S(O)2NR 16N R 17N , or R 4Q3 and R 5Q3 Together as -(CH2)-N(R) 8 )-(CH2)-, R 8 It is (C1-C4)-alkoxy, -C(O)(C1-C4)-alkyl, -C(O)-(C3-C6)-cycloalkyl or -S(O)2C(R 11N )R 12N R 13N ; R 5N This indicates substituents independently selected from hydrogen and (C1-C6)-alkyl groups. R 6N This indicates that the components are independently selected from hydrogen, (C1-C6)-alkyl, and -C(O)-C(R). 11N )R 12N R 13N Substituents, R 11N It is hydrogen; R 12N It is hydrogen; R 13N It can be hydrogen or methyl; R 16N It is hydrogen or (C1-C6)-alkyl; R 17N It is hydrogen or (C1-C6)-alkyl; G represents hydrogen, an agriculturally acceptable metal, or C(O)-R. 14 or -C(O)-OR 15, R 14 It is (C1-C6)-alkyl. R 15 It is (C1-C6)-alkyl.
[0070] In another embodiment of the invention, the herbicide / safety agent combination of the invention preferably comprises compounds A1, A3, A5, A7 and A9 from Table 1 above, or their agrochemically acceptable salts [safety agent (A)], and preferably comprises compounds of formula (II-1) active herbicide components listed in Table 2 below [herbicide (B)], wherein Q is Q-1, and R 1 R 2 R 3 The definitions of , W, Y, Z and G, as well as n1 and n2 are as follows.
[0071] Table 2 In another embodiment of the invention, the herbicide / safety agent combination of the invention preferably comprises compounds A1, A3, A5, A7 and A9 from Table 1 above, or their agrochemically acceptable salts [safety agent (A)], and preferably comprises compounds of formula (II-2) active herbicide components listed in Table 3 below [herbicide (B)], wherein Q is Q-2, and Y and G are defined as follows, and wherein R 1 It is 1-propynyl, R 2 and R 3 Each is a methyl group, and W and Z are both CH2, and n1 is 2.
[0072] Table 3 In another embodiment of the invention, the herbicide / safety agent combination of the invention preferably comprises compounds A1, A3, A5, A7 and A9 from Table 1 above, or their agrochemically acceptable salts [safety agent (A)], and preferably comprises compounds of formula (II-3) active herbicidal components listed in Table 4 below [herbicide (B)], wherein Q is Q-3, and G has the following definition, and wherein R 1 It is 1-propynyl, R 2 and R3 Each is a methyl group, and W and Z are each CH2 groups, and R... 1Q3 It is hydrogen, and R 2Q3 -C(O)NR 5N R 6N , where R 5N and R 6N Each is a methyl group.
[0073] Table 4 In another embodiment of the invention, the herbicide / safety agent combination of the invention preferably comprises compounds A1, A3, A5, A7 and A9 from Table 1 above, or their agrochemically acceptable salts [safety agent (A)], and preferably comprises compounds of formula (II-4) active herbicidal components listed in Table 5 below [herbicide (B)], wherein Q is Q-3, and R 5Q3 The definitions of R and G are as follows, and R is a subset of G. 1 It is 1-propynyl, R 2 and R 3 Each is a methyl group, and W and Z are each CH2, and R is... 1Q3 and R 2Q3 The groups together form -(CH2). nq1 -C(R 4Q3 )R 5Q3 -(CH2) nq2 -where nq1 and nq2 are each 2, and R 4Q3 It is hydrogen.
[0074] Table 5 In another embodiment of the invention, the herbicide / safety agent combination of the invention preferably comprises compounds A1, A3, A5, A7 and A9 from Table 1 above, or their agrochemically acceptable salts [safety agent (A)], and preferably comprises compounds of active herbicidal components of formula (II-5) listed in Table 6 below [herbicide (B)], wherein Q is Q-3, and G has the following definition, and wherein R 1 It is 1-propynyl, R 2 and R 3 Each is a methyl group, and W and Z are each CH2, and R is... 1Q3 and R 2Q3 The groups together form -(CH2). nq1 -C(R 4Q3 )R 5Q3 -(CH2) nq2- where nq1 and nq2 are each 1, R 4Q3 and R 5Q3 The groups together form -(CH2)-N(R) 8 )-(CH2)-, and where R 8 It is -(CO)CH3.
[0075] Table 6 In the context of this invention, various preferred and more preferred embodiments can be combined with each other as needed. This means that herbicidal compositions containing a safener (A) or one or more compounds of general formula (I) or an agriculturally chemically acceptable salt thereof [component (A)] and (B) one or more herbicides [component (B)] are included within this invention, wherein, as detailed above, any desired preferred and more preferred embodiments disclosed can be combined with each other.
[0076] On the date of application, it was unexpectedly discovered that binary compositions comprising a compound (A) of general formula (I) as a safener or an agriculturally chemically acceptable salt thereof [safener (A)] and a herbicide (B) were particularly advantageous.
[0077] These are detailed in Table 7 below.
[0078] Table 7: Preferred Combinations In another embodiment, the following combinations shown in Table 8 are preferred: Table 8: Other Preferred Combinations Furthermore, the herbicide / safener combination of the present invention can be used with other active ingredients such as fungicides, insecticides, acaricides, etc., and / or adjuvants such as adjuvants and formulation auxiliaries in conventional additives used in plant growth regulators or crop protection. They are used in the form of formulations or tank mixes as herbicide products (compositions).
[0079] Therefore, the present invention also provides herbicide / safety agent combinations for adding conventional additives (such as adjuvants and formulation adjuvants) to crop protection, as well as optionally other active crop protection ingredients.
[0080] The present invention also provides the use and application method of the herbicide / safety agent combination of the present invention as a herbicide and a plant growth regulator, preferably the herbicide / safety agent combination of the present invention as a herbicide and a plant growth regulator having a synergistic activity content of the corresponding herbicide combination present.
[0081] For the active ingredient in group (B), the application rate is preferably 5 to 400 g ai / ha, particularly 8 to 200 g / ha, and most preferably 10 to 90 g ai / ha.
[0082] Depending on the effective application rate, the ratio of (A):(B) by weight is typically 1:400 to 500:1, preferably 1:100 to 100:1, and more preferably 1:40 to 20:1.
[0083] The amount is the application rate (g ai / ha = grams of active substance per hectare), and thus also defines the proportion of active ingredients combined in combination formulations, premixes, tank mixes, or sequential applications.
[0084] The herbicide / safety agent combination of the present invention may contain other components, such as other active ingredients targeting harmful organisms (e.g., harmful plants, plant-damaging animals, or plant-damaging fungi), in which case, in particular, active ingredients of fungicides, insecticides, acaricides, nematicides, miticides, and related substances are selected.
[0085] Fungicidal active compounds that can be used in combination with the herbicide / safener combination of the present invention, preferably standard commercially available active ingredients, such as (similar to herbicides, said compounds are generally named by their common names): 1) Ergosterol biosynthesis inhibitors, such as cyproconazole, difenoconazole, epoxiconazole, fenhexamid, fenpropidin, fenpropimorph, fenpyrazamine, fluquinconazole, flutriafol, imazalil, imazalil sulfate, ipconazole, and m-methoxyfenozide. etconazole, myclobutanil, paclobutrazole, prochloraz, propiconazole, prothioconazole, pyrisoxazole, spiroxamine, tebuconazole, tetraconazole, triadimenol, tridemorph, triticonazole, (1R,2S,5S)-5 -(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)but-2-ol, (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)but-2-ol, (2R)-2-[4-(4-chlorophenoxy)-2 [-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)prop-2-ol, (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)but-2-ol, (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)but-2-ol, (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)prop-2-ol, (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,[2-oxazol-4-yl](pyridin-3-yl)methanol, (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolane-2-yl}methyl)-1H-1,2,4-triazole, 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolane-2-yl}methyl)-1H- 1,2,4-Triazole, 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-1H-1,2,4-triazole-5-yl thiocyanate, 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-1H-1,2,4-triazole-5-yl thiocyanate, 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-1H-1,2,4-triazole-5-yl thiocyanate, 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl] [2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-] [(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,[6-Trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)prop-2-ol, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)but-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)-phenyl]-1-(1H-1,2,4-triazol-1-yl)but- 2-Alcohol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thione, 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol- 3-Thione, 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thione, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, 5-(allylthioalkyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-1H-1,2,4-triazole, 5-(allylthioalkyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-1H-1,2,4-triazole, 5-(allylthioalkyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-1H-1,2,4-triazole, 5-(rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxetane-2-yl]methyl}-1H-1,2,4-triazole Cyclopropane-2-yl]methyl}-1H-1,2,4-triazole, 5-(allylthio)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxacyclopropane-2-yl]methyl}-1H-1,2,4-triazole, N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]thio]phenyl}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]thio]phenyl}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{[3-(2,2,3,3-Tetrafluoropropoxy)phenyl]thioalkyl}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]thioalkyl}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)thioalkyl]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)thioalkyl]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)thioalkyl]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,2) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)thioalkyl]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide, N'-(4-{[3-(difluoromethoxy)phenyl]thioalkyl}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, N'-(4-{3-[(difluoromethyl)thioalkyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, N'-(4-{3-[(difluoromethyl)thioalkyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide) Amides, N'-[5-bromo-6-(2,3-dihydro-1H-indene-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methyliminocarboxamide, N'-{4-[(4,5-dichloro-1,3-thiazo-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methyliminocarboxamide, N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, mefentrifluconazole, ipfentrifluconazole.
[0086] 2) Respiratory chain inhibitors acting on complexes I or II, such as benzovindiflupyr, bixafen, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, furamettapyr, isofetamid, isopyrazam (trans-epomers 1R, 4S, 9S), and isopyrazam (trans-epomers 1S, 4R, 9R). Azoxystrobin (trans-episode racemic 1RS, 4SR, 9SR), pyraclostrobin (a mixture of cis-episode racemic 1RS, 4SR, 9RS and trans-episode racemic 1RS, 4SR, 9SR), pyraclostrobin (cis-episode enantiomers 1R, 4S, 9R), pyraclostrobin (cis-episode enantiomers 1S, 4R, 9S), pyraclostrobin (cis-episode racemic 1RS, 4SR, 9RS), penflufen, penthiopyrad, pydiflumetofen, bifenazate (pyr) Aziflumid, sedaxane, 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)-1H-pyrazole-4-carboxamide, 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, 2-fluoro-6 ... 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)benzamide, 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-Dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide 5,8-Difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N- (2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-[(1R,4S)-9 -(dichloromethylene)-1,2,3,4-tetrahydro-1,4-bridged methylenenaphthalene-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-bridged methylenenaphthalene-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[1-(2,[4-Dichlorophenyl)-1-methoxypropyl-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole- 4-Carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole- 4-Thiocarboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide -Formamide, N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
[0087] 3) Respiratory chain inhibitors acting on complex III, such as ametoctradin, amisulbrom, azoxystrobin, coumethoxystrobin, coumoxystrobin, cyazofamid, dimoxystrobin, enoxastrobin, famoxadon, fenamidon, flufenoxystrobin, and fluazoxystrobin. (fluoxastrobin), kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)methylene Ethyl]amino}oxy]methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridine- [2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxacyclopentan-7-yl 2-methylpropionate, 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-carbamate-2-hydroxybenzamide, (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate.
[0088] 4) Inhibitors of mitosis and cell division, such as carbendazim, diethofencarb, ethaboxam, fluopicolide, pencycuron, thiabendazole, thiophanate-methyl, zoxamide, 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)- 6-Methylpyridazine, 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine Pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.
[0089] 5) Compounds with multi-site activity, such as Bordeaux mixture, captafol, captan, chlorthalonil, copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate (2+), dithianon, dodine, folpet, mancozeb, mancozeb, metiram, zinc metiram, copper quinoline. oxine), propineb, sulfur and sulfur preparations including calcium polysulfides, thiram, zineb, ziram, 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiainro[2,3-c][1,2]thiazolyl-3-carboxylonitrile.
[0090] 6) Compounds that can stimulate host defense, such as acibenzolar-S-methyl, isothiazine, probenazole, and tiadinil.
[0091] 7) Inhibitors of amino acid and / or protein biosynthesis, such as cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, oxytetracycline, pyrimethanil, and 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-1-yl)quinoline.
[0092] 8) ATP production inhibitors, such as silthiofam.
[0093] 9) Cell wall synthesis inhibitors, such as benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid, pyrimorph, valifenalate, (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, and (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.
[0094] 10) Inhibitors of lipid and membrane synthesis, such as propamocarb, propamocarb hydrochloride, and tolclofos-methyl.
[0095] 11) Inhibitors of melanin biosynthesis, such as tricyclazole and 2,2,2-trifluoroethyl-{3-methyl-1-[(4-methylbenzoyl)amino]but-2-yl}carbamate.
[0096] 12) Nucleic acid synthesis inhibitors, such as: benalaxyl, benalaxyl-M (kiralaxyl) and metalaxyl.
[0097] 13) Signal transduction inhibitors, such as fludioxonil, iprodione, procymidone, proquinazid, quinoxyfen, and vinclozolin.
[0098] 14) Compounds that can be used as uncoupling agents, such as fluazinam and meptyldinocap.
[0099] 15) Other compounds, such as abscisic acid, bethiozine, bethoxazin, capsimycin, carvone, chinomethionat, cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium, methylisothiocyanate, metrafenon, mildiomycin, natamycin, nickel dimethyl dithiocarbamate. dimethyldithiocarbamate), nitrothal-isopropyl, oxamocarb, oxathiapiprolin, oxyfenthiin, pentachlorophenol and its salts, phosphonic acid and its salts, propamocarb-fosetylate, pyriofenone (chlazafenone), tebufloquin, tecloftalam, tolnifanide, 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazolyl}piperidin-1-yl)-2-[5-methyl -3-(trifluoromethyl)-1H-pyrazol-1-yl] acetone, 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazo-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl] acetone, 2-(6-benzylpyridin-2-yl)quinazolin, 2,6-dimethyl-1H,5 ... H-[1,4]dithiacino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazo-2-yl)piperidin-1-yl]acetone, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazolyl)piperidin-1-yl] acetone, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazolyl)piperidin-1-yl] acetone, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl] quinazolin, 2-{(5R 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazo-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, 2-{2-[(7,8-difluoro-2-methylquinoline-3-yl)oxy]-6-fluorophenyl}prop-2-ol, 2-{2-fluoro-6-[(8-fluoro-2-yl]-[2-[2-[2-[2-[(7,8-difluoro-2-methylquinoline-3-yl)oxy]-6-fluorophenyl]prop-2-ol, 2-{2-fluoro-6-[(8-fluoro-2-[2-[2-[2-[2-[(2-[(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidin-4-yl)-1,3-thiazo-4-yl]-4,5-dihydro-1,2-oxazol-5-yl]-3-chlorophenylmethanesulfonate, 2-{2-[2-[(7,8-difluoro-2-methylquinoline-3-yl)oxy]-6-fluorophenyl]prop-2-ol, 2-{2-fluoro-6-[(8-fluoro-2-[2-[2-[(2-[(2-[(3,5-difluoro-2-[(2-[(3,5-difluoromethyl)-1H-pyrazol-1-yl]acetyl]-[2-[(2-[(7,8-difluoro- ... 2-(3-methylquinoline-3-yl)oxy]phenyl}prop-2-ol, 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazo-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazo-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate, 2-phenylphenol and its salts, 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1- 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1-yl)quinoline, 4-amino-5-fluoropyrimidin-2-ol (tautomer form: 4-amino-5-fluoropyrimidin-2(1H)-one), 4-oxo-4-[(2-phenylethyl)amino]butyric acid, 5-amino-1,3,4-thiadiazol-2-thiol, 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazine, 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, 9-fluoro-2,2-dimethyl-5-(quinoline-3-yl)-2,3-dihydro-1,4-Benzoxazacycloheptenene, but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (2Z)-3-amino-2-cyano-3-phenylacrylate, phenazin-1-carboxylic acid, propyl 3,4,5-trihydroxybenzoate, quinoline-8-ol, quinoline-8-ol sulfate (2:1), {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate tert-butyl ester, 5-fluoro-4-imino-3-methyl-1-sulfonyl]-3,4-dihydropyrimidin-2(1H)-one,
[0100] Preferred fungicides are selected from: benalaxyl, bitertanol, bromuconazole, captafol, carbendazim, carpropamid, cyazofamid, cyproconazole, diethofencarb, edifenphos, fenpropimorph, fentine, fluquinconazole, fosetyl, fluoroimide, folpet, and iminoctadin. e) iprodionem, iprovalicarb, kasugamycin, mancozeb, nabam, pencycuron, prochloraz, propamocarb, propineb, pyrimethanil, spiroxamine, quintozene, tebuconazole, tolylfluanid, triadimefon, triadimenol, trifloxystrobin, zineb.
[0101] Insecticides, acaricides, nematicides, miticides and their related active ingredients are, for example (similar to herbicides and fungicides, where the compound is referred to by its common name, if possible): (1) Acetylcholinesterase (AChE) inhibitors, preferably carbamates, selected from alanycarb, aldicarb, bendicarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiazole. ocarb), isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates selected from acephate, azamethiphos, ethyl methacrylate, etc. Azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, didrotop hos), dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, O-(methoxyaminothiophosphoryl)salicylic acid isopropyl ester,Isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, and other similar pesticides. Piririmiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion.
[0102] (2) GABA-gated chloride channel blockers, preferably cyclodiene-organochlorines selected from chlordane and endosulfan; or fiproles selected from ethiprole and fipronil.
[0103] (3) Sodium channel modulators, preferably pyrethroids, selected from acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyfluthrin, γ-cyfluthrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin. hrin), empenthrin [(EZ)-(1R) isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer], tralomethrin and transfluthrin or DDT or methoxychloride.
[0104] (4) Competitive modulators of nicotinic acetylcholine receptors (nAChR), preferably neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or nicotine; or sulfoxide imines selected from sulfoxaflor; or butenolides selected from flupyradifurone.
[0105] (5) Allosteric modulators of nicotinic acetylcholine receptors (nAChR), preferably spinosins, selected from spinotomycin and spinosad.
[0106] (6) Allosteric regulators of glutamate-gated chloride channels (GluCl), preferably avermectins / milbemycins, selected from abamectin, emamectin benzoate, lepimectin and milbemectin.
[0107] (7) Juvenile hormone analogues, preferably selected from the following juvenile hormone analogues: hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.
[0108] (8) Other non-specific (multi-site) inhibitors, preferably alkyl halides selected from methyl bromide and other alkyl halides; or chloropicrin or thiofluoride or borax or tartar or methyl isocyanate generating agents selected from diazomet and thiocyanate.
[0109] (9) String organ TRPV channel modulators, selected from pymetrozine and pyrifluquinazone.
[0110] (10) Mite growth inhibitors, selected from clofentezine, hexythiazox, diflovidazin and etoxazole.
[0111] (11) Insect midgut membrane microbial disruptors, selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and Bt plant proteins selected from the following: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1 / 35Ab1.
[0112] (12) Mitochondrial ATP synthase inhibitor, preferably an ATP interferon, such as diafenthiuron; or an organotin compound, such as azocyclotin, cyhexatin and fenbutatin oxide; or propargite or tetradifon.
[0113] (13) Uncoupling agents that block the oxidative phosphorylation of the proton gradient, selected from chlorfenapyr, DNOC and sulfluramid.
[0114] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.
[0115] (15) Chitin biosynthesis inhibitor, type 0, selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.
[0116] (16) Chitin biosynthesis inhibitor, type 1, which is selected from buprofezin.
[0117] (17) Molting disruptors (especially in the case of Diptera), which are selected from cyromazine.
[0118] (18) Ecdysone receptor agonists selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
[0119] (19) Octopamine receptor agonist, which is selected from amitraz.
[0120] (20) Inhibitors of electron transport in mitochondrial complex III, selected from hydramethylnon, acequinocyl and fluacrypyrim.
[0121] (21) Mitochondrial complex I electron transport inhibitor, preferably a METI acaricide selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).
[0122] (22) Voltage-dependent sodium channel blockers selected from indoxacarb and metaflumizone.
[0123] (23) Acetyl-CoA carboxylase inhibitor, preferably tetronic acid and tetramic acid derivatives, selected from spirodiclofen, spiromesifen and spirotetramat.
[0124] (24) An inhibitor of electron transport in mitochondrial complex IV, preferably a phosphide selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or a cyanide selected from calcium cyanide, potassium cyanide and sodium cyanide.
[0125] (25) An inhibitor of electron transport in mitochondrial complex II, preferably a β-ketonitrile derivative selected from cyenopyrafen and cyflumetofen; or a carboxanilide selected from pyflubumide.
[0126] (28) ryanodine receptor modulators, preferably diamides selected from chlorantraniliprole, cyantraniliprole and flubendiamide.
[0127] (29) A string organ modulator (with an indeterminate target structure) selected from flonicamid.
[0128] (30) Other active ingredients are selected from: acynonapyr, bispyribac-methyl, afoxolaner, azadirachtin, benclothiaz, benzoximate, benzpyrimoxan, bifenazate, broflanilide, bromopropylate, chinomethionat, chloroprallethrin, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol, and epsilon.Metofluthrin, ε-momfluthrin, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, flupyrimin, fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, κ-bifenthrin, κ-heptafluthrin, lotelanar Laner, meperfluthrin, oxazosulfyl, paichongding, pyridalyl, pyrifluquinazon, pyriminostrobin, spirobudiclofen, spiropidion, tetramethylfluthrin, tetraliprole, tetrachlorantraniliprole, tigolaner, tioxazafen, thiofluoximate, triflumezopyrim, and iodomethane; additionally based on Bacillus thuringiensis. Formulations of firmus (I-1582, BioNeem, Votivo) and the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (as known by WO 2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl) methyl ketone (as known by WO 2003 / 106457) (CAS 885026-50-6). 637360-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (as known from WO 2006 / 003494) (CAS872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (from WO2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (from EP 2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (from WO 2004 / 099160 (CAS792914-58-0), PF1364 (obtained from JP 2010 / 018586) (CAS 1204776-60-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoroprop-2-one (obtained from WO 2013 / 144213) (CAS1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (obtained from WO 2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (as known from CN103232431) (CAS) 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thioheterocyclic butyl)benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxo-3-thioheterocyclic butyl)benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thioheterocyclic butyl)benzamide (by WO 2013 / 050317)(A1 obtained) (CAS1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazole-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propionamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazole-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propionamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazole-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propionamide (obtained from WO 2013 / 162715 A2, WO 2013 / 162716 A2, US 2014 / 0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carboxylonitrile (obtained from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (thiobenzamide (Liudaibenjiaxuanan), obtained from CN 103109816A) (CAS 1232543-85-9), N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (as per WO 2012 / 034403 A1) (CAS1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (as per WO 2011 / 085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine (as known from CN 101337940 A) (CAS 1108184-52-6), (2E)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazine carboxamide and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazine carboxamide (as known from CN 101715774 A) (CAS1232543-85-9), cyclopropanecarboxylic acid 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl ester (obtained from CN 103524422 A) (CAS 1542271-46-4), (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indo[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (obtained from CN 102391261 A) (CAS 1370358-69-2), 6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose (as known from US 2014 / 0275503 A1) (CAS 1181213-14-8), 8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 933798-27-7), (8-cis)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (obtained from WO 2007040280A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propionamide (as determined by WO 2015 / 058021 A1, WO 2015 / 058028 A1) (CAS 1477919-27-9) and N-[4-(aminothiomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-carboxamide (as determined by CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxane-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]pyrimidine (as determined by WO 2013 / 115391A1 (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (obtained from WO 2014 / 187846 A1) (CAS1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylcarboxylate (obtained from WO2010 / 066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[(4R)-2-ethyl-3-oxo-4-isoxazolyl]-2-methylbenzamide (obtained from WO 2011 / 067272, WO2013 / 050302) (CAS 1309959-62-3).
[0129] For example, the following insecticides are preferably used in conjunction with the herbicide / safety agent combination of the present invention: Acetamiprid, flufenoxuron, aldicarb, amitraz, methyl glutathione, cypermethrin, carbaryl, cypermethrin, deltamethrin, endosulfan, ethoprophos, fenthion, fipronil, imidacloprid, methamidophos, methyl thiocarb, niclosamide, sulfoxide, prothiophos, flusilazole, thiamethoxam, thiamethoxam, tetrabromopyr, triazophos, trichlorfon, chlorfenapyr, terbufos, fonofos, phorate, chlorpyriphos, carbofuran, heptafluthrin.
[0130] The herbicide / safety agent combination of the present invention is preferably applicable to the control of unwanted plant growth in economically important crops such as wheat (durum and soft wheat), corn, soybean, sugar beet, sugarcane, cotton, rice, legumes (e.g., dwarf beans and broad beans), flax, barley, oats, rye, triticale, potato, and millet / sorghum.
[0131] For application, the herbicide / safety agent combination of the present invention can be applied together or separately to plants (e.g., harmful plants, such as monocot or dicot weeds or unwanted crop plants), seeds (e.g., cereals, seeds or vegetative reproductive organs such as tubers or budding parts of new shoots) or areas where plants grow (e.g., growing zones).
[0132] Herbicide / safety agent combinations can be applied before sowing (and, if appropriate, mixed into the soil), pre-emergence, or post-emergence. For harmful plants that have not yet emerged or have already emerged, early pre-emergence or post-emergence methods are preferred. Application can also be integrated into a weed management system with multiple, repeated applications (sequential treatments).
[0133] Some representative specific examples of monocotyledonous and dicotyledonous weeds that can be controlled by the herbicide / safety agent combination of the present invention are as follows, although these enumerations are not intended to impose restrictions on any particular species.
[0134] Among monocotyledonous weed genera, such as *Aegilops*, *Agropyron*, *Agrostis*, *Alopecurus*, *Apera*, *Avena*, *Brachicaria*, *Bromus*, *Cynodon*, *Dactyloctenium*, *Digitaria*, *Echinochloa*, *Eleocharis*, *Eleusine*, *Eragrostis*, *Eriochloa*, *Festuca*, and *Fimbristylis*. The genera *Imperata*, *Ischaemum*, *Heteranthera*, *Leptochloa*, *Lolium*, *Monochoria*, *Panicum*, *Paspalum*, *Phalaris*, *Phleum*, *Poa*, *Rottboellia*, *Sagittaria*, *Scirpus*, *Setaria*, *Sorghum*, *Sphenoclea*, and *Cyperus* belong to the annual plant family.
[0135] In terms of dicotyledonous weed species, its scope extends to the following genera, such as *Abutilon*, *Amaranthus*, *Ambrosia*, *Anoda*, *Anthemis*, *Aphanes*, *Artemisia*, *Atriplex*, *Bellis*, *Bidens*, *Capsella*, *Carduus*, and *Cassia*. *Sia*, *Centaurea*, *Chenopodium*, *Cirsium*, *Convolvulus*, *Datura*, *Desmodium*, *Emex*, *Erodium*, *Erysimum*, *Euphorbia*, *Galeopsis*, *Galinsoga*, *Galium* Genuses of the genera *Geranium*, *Hibiscus*, *Ipomoea*, *Kochia*, *Lamium*, *Lepidium*, *Lindernia*, *Matricaria*, *Mentha*, *Mercurialis*, *Mullugo*, *Myosotis*, *Papaver*, *Pharbitis*, *Plantago*, *Polygonum*, *Portulaca*, *Ranunculus*, *Raphanus* The genera include: phanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, and Xanthium.
[0136] If the herbicide / safety agent combination of the present invention is applied to the soil surface before germination, it will either completely prevent the germination of weed seedlings, or the weeds will stop growing after reaching the cotyledon stage and eventually die completely after three to four weeks.
[0137] If the herbicide / safety agent combination of the present invention is applied to the green parts of the plant after emergence, growth ceases after treatment, and harmful plants remain at the growth stage at the time of application, or die completely after a period of time. Therefore, this treatment can eliminate competition from harmful weeds very early and continuously. In contrast, the growth of the crop is only slightly affected (if any) by the use of this herbicide / safety agent combination.
[0138] The herbicide / safener combination of this invention is known for its rapid onset and long-lasting weed control. Typically, the active ingredients in the composition of this invention exhibit good resistance to rain washout. A particular advantage is that the effective dosages of components (A) and (B) used in the herbicide / safener combination can be adjusted to such low levels that their effect on the soil is optimally low. Therefore, its use in sensitive crops is not only feasible but also effectively prevents groundwater contamination.
[0139] The herbicide / safety agent combination of the present invention is applicable to economically important crops, such as dicotyledonous crops: *Arachis*, *Beta*, *Brassica*, *Cucumis*, *Cucurbita*, *Helianthus*, *Daucus*, *Glycine*, *Gossypium*, *Ipomoea*, *Lactuca*, *Linum*, *Lycopersicon*, and tobacco. Genera including *Nicotiana*, *Phaseolus*, *Pisum*, *Solanum*, *Vicia*, or monocotyledonous genera: *Allium*, *Ananas*, *Asparagus*, *Oats*, *Hordeum*, *Oryza*, *Panicum*, *Saccharum*, *Secale*, *Sorghum*, *Triticale*, *Triticum*, and *Zea*.
[0140] The herbicide / safety agent combination of the present invention is preferably used in genetically modified crops that are resistant to growth regulators or herbicides that inhibit essential plant enzymes (e.g., acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS), protoporphyrinogen IX oxidase (PPO), or hydroxyphenylpyruvate dioxygenase (HPPD)), or resistant to sulfonylureas, glyphosate, glufosinate, or benzoylisoxazole herbicides and similar active ingredients.
[0141] The herbicide / safety agent combination of the present invention can be in the form of a mixture of components (A) and (B) with (where appropriate) other active agrochemicals, additives and / or conventional formulation adjuvants, and then applied by diluting with water in a conventional manner; or it can be prepared as a so-called tank mix by co-diluting separately or partially separately formulated components with water.
[0142] The herbicide / safener combination of the present invention can be formulated in a variety of ways according to desired biological and / or physicochemical parameters. Examples of common formulation choices include: wettable powder (WP), water-soluble powder (SP), emulsifiable concentrate (EC), water-soluble concentrate, aqueous solution (SL), emulsion (EW) such as water-in-oil and oil-in-water emulsions, sprayable solutions or emulsions, oil-based or water-based dispersants, oil dispersants (OD), suspension emulsions, suspension concentrates (SC), oil-miscible solvents, microcapsule suspensions (CS), dusting products (DP), coating agents, granules for soil application or broadcasting, granules in microparticle form (GR), sprayable granules, absorbent and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, or waxes.
[0143] Therefore, the present invention also provides a herbicidal and plant growth regulating composition comprising the herbicide / safety agent combination of the present invention.
[0144] The types of formulations are known in principle and described in, for example, the following literature: Winnacker-Küchler, "Chemische Technologie" [Chemical technology], Vol. 7, C. Hanser Verlag Munich, 4th edition, 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd edition, 1979, G. Goodwin Ltd. London.
[0145] Essential formulation adjuvants such as inert materials, surfactants, solvents, and other additives are also known and documented in, for example, the following literature: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ; Hv Olphen, "Introduction to Clay Colloid Chemistry"; 2nd ed., J. Wiley & Sons, NY Marsden; "Solvents Guide", 2nd ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte" ["Interface-active EthyleneOxide Adducts"], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th edition, 1986.
[0146] Based on these formulations, compounds can also be prepared with other pesticide active substances, such as other herbicides, fungicides, insecticides or other pesticides (e.g., acaricides, nematicides, molluscicides, rodenticides, aphicides, birdicides, larvicides, ovicides, fungicides, viricides, etc.), as well as other safeners, fertilizers and / or growth regulators, for example in the form of finished formulations or tank mixes.
[0147] Wettable powders are formulations that can be uniformly dispersed in water. In addition to the active ingredient, diluent, or inert substance, they contain ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyethylene glycol ether sulfates, alkyl sulfonates, alkylbenzene sulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl taurate. To prepare wettable powders, the herbicidal active ingredient is finely ground, for example, in conventional equipment such as a hammer mill, air mill, or air jet mill, and mixed simultaneously or subsequently with formulation adjuvants.
[0148] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (e.g., butanol, cyclohexanone, dimethylformamide, xylene, or a relatively high-boiling aromatic compound or hydrocarbon, or a mixture of organic solvents) and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium alkyl aryl sulfonates, such as calcium dodecylbenzene sulfonate; or nonionic emulsifiers, such as fatty acid polyethylene glycol esters, alkyl aryl polyethylene glycol ethers, fatty alcohol polyethylene glycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, and sorbitol esters (e.g., sorbitol fatty acid esters, or polyoxyethylene sorbitol fatty acid esters).
[0149] Powdered products are obtained by grinding active ingredients together with finely dispersed solids (such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth).
[0150] The suspension concentrate can be water-based or oil-based. For example, it can be prepared by wet milling, for example, using a commercially available bead mill and optionally by adding surfactants, such as those listed above for other types of formulations.
[0151] Emulsions, such as oil-in-water emulsions (EW), can be prepared using, for example, agitators, colloid mills, and / or static mixers, as well as aqueous organic solvents and optional surfactants listed above for other types of formulations.
[0152] Granules can be prepared by spraying the active ingredient onto an absorbent granular inert material or by applying a concentrated active ingredient onto the surface of a carrier material (e.g., sand, kaolinite, or granular inert material) using an adhesive (e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oil). Suitable active ingredients can also be granulated using methods conventional for fertilizer granulation—if mixing with fertilizer is required.
[0153] Water-dispersible granules are typically prepared by methods such as spray drying, fluidized bed granulation, disc granulation, mixing with a high-speed mixer, and extrusion without the use of solid inert materials.
[0154] This agrochemical formulation typically contains 0.1% to 99% by weight, particularly 0.2% to 95% by weight, of the active ingredient of component (A) and / or (B), with the following concentrations being standard concentrations depending on the formulation type: In wettable powders, the concentration of the active ingredient is, for example, from about 10% to 95% by weight; the balance, up to 100% by weight, consists of conventional formulation ingredients. In the case of emulsifiable concentrates, the concentration of the active ingredient can be from about 1% to 90% by weight, preferably from 5% to 80% by weight.
[0155] Powder formulations typically contain 5% to 20% by weight of the active ingredient; sprayable solutions contain about 0.05% to 80%, preferably 2% to 50%, of the active ingredient.
[0156] In the case of granules, such as dispersible granules, the content of the active ingredient depends in part on whether the active ingredient is in liquid or solid form, as well as the granulation aids and fillers used. Typically, the content in water-dispersible granules is from 1% to 95% by weight, preferably from 10% to 80% by weight.
[0157] In addition, the active ingredient formulation optionally includes corresponding conventional adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, defoamers, evaporation inhibitors and pH- or viscosity-regulating agents.
[0158] For application, commercially available formulations are diluted in a conventional manner, if appropriate, such as with water in the case of wettable powders, emulsifiable concentrates, dispersants, and water-dispersible granules. Powder formulations, granules for soil application or broadcasting, and sprayable solutions generally do not require further dilution with other inert substances before application.
[0159] The herbicide / safety agent combination of the present invention can be applied to plants, plant parts, plant seeds or planting areas (soil), preferably to green plants and plant parts, and optionally additionally to the soil.
[0160] One possible method of use is to apply the herbicide / safety agent combination in a tank mix, in which the optimally formulated concentrated formulations of the individual active ingredients are mixed with water in a tank, and then the resulting spray is applied.
[0161] Because the amounts of the components have been adjusted to the appropriate proportions, the combined formulation of the herbicide / safener of the present invention has the advantage of being easier to apply. Furthermore, the adjuvants in the formulation can be optimally adjusted to each other; however, tank mixes of different formulations may result in unwanted adjuvant combinations.
[0162] General Formulation Examples a)-f) a) The powdered product is obtained by mixing 10 parts by weight of component (A) or (B), or a mixture of components (A) + (B) (and optionally other components) and / or its salt with 90 parts by weight of talc as an inert substance, and grinding them in an impact mill.
[0163] b) A wettable powder that is easily dispersible in water is obtained by mixing 25 parts by weight of a component / component mixture, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignin sulfonate and 1 part by weight of sodium oleoylmethyl taurate as a wetting agent and dispersant, and grinding the mixture in a pin mill.
[0164] c) A dispersible concentrate readily dispersible in water is prepared by mixing 20 parts by weight of the component / component mixture with 6 parts by weight of alkylphenol polyethylene glycol ether (Triton® X 207), 3 parts by weight of isotridecyl polyethylene glycol ether (8 EO), and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to 277). o C) Mix and grind the mixture in a friction ball mill to a fineness of less than 5 micrometers to obtain the desired result.
[0165] d) The emulsifiable concentrate is obtained by mixing 15 parts by weight of component / component mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
[0166] e) Water-dispersible granules are obtained by mixing the following substances: The components of a 75-part by weight mixture 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol, and 7 parts by weight of kaolin, The mixture is ground in a pin-disc mill and granulated in a fluidized bed by spraying water as a granulation liquid.
[0167] f) Water-dispersible granules can also be obtained by homogenizing and pre-grinding the following substances on a colloid mill: The components of a 25-part by weight mixture, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate 2 parts by weight of sodium oleoylmethyl taurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate, and 50 parts by weight of water, The mixture was then ground in a ball mill, and the resulting suspension was atomized and dried in a spray tower using a single-phase nozzle.
[0168] Biological Examples The efficacy of the selected herbicide / safety agent combination of the present invention: The crop seeds to be treated were placed in soil in plastic pots (approximately 7 cm in diameter), covered with soil, and then grown in a greenhouse under favorable germination and growth conditions. The experimental plants were treated at the early leaf stage (BBCH 12).
[0169] The safeners used (the inventive safener being compound A3, and the comparative safeners being mefenpyr-diethyl and cloquintocet) were sprayed onto the aboveground parts of the plants in the form of wettable powder (WP) at a dosage of 100 g / ha and a water application rate equivalent to 300 l / ha.
[0170] Subsequently, herbicides (component B, selected from: B1-6, B1-38, B1-42, B1-46, B1-66, B1-68) were applied. For this purpose, the herbicides used were formulated as wettable powders (WP), emulsifiable concentrates (EC), and / or water-soluble concentrates (SL), mixed according to the appropriate dosage, and sprayed onto the aboveground parts of the plants at a water application rate equivalent to 300 l / ha, with the addition of formulation adjuvants (Mero, 1.5 l / ha, and diammonium phosphate (DAP), 1 g / ha).
[0171] The selected herbicide dosage resulted in damage rates of 45% to 98% in the control group (herbicide without a safener). Experience suggests that this allows for optimal visual assessment of the safener's effectiveness under greenhouse conditions.
[0172] Following application, plants were cultivated in a greenhouse under favorable growing conditions. Damage was visually assessed 21 days after application. Damage was assessed in the range of 0-100% by comparison with untreated control plants, and each treatment was replicated an average of twice.
[0173] Example: 0% = No noticeable effect compared to untreated plants. 20% = The treated plant population showed 20% damage compared to the untreated control population (e.g., growth height, leaf damage, etc.). 100% = The treated plants are completely damaged / die.
[0174] The trials showed that by adding a safener (component (A)), the damage to barley crops (HORVS; variety: Accordine) caused by each herbicide (component (B)) was significantly reduced (= herbicide damage without a safener). The application rate of each safener was 100 g / ha. In particular, a very strong safener effect was found when compound A3 was used as a safener component compared to the known safeners pyrazosulfuron and quinalazine (see Tables 9 and 10).
[0175] Table 9: Effects of safeners in HORVS; Comparison of safener A3 and pyrazosulfuron-methyl Table 10: Effects of safety agents in HORVS; Comparison of safety agent A3 and antidote quinine.
Claims
1. A herbicide / safener combination comprising one or more compounds (A) and one or more herbicidal active compounds (B), wherein (A) represents one or more compounds of general formula (I) or an agriculturally chemically acceptable salt thereof. And among them, (R a ) p -Phenyl groups represent Q-1.1 to Q-1.55 groups: And (R) b ) q -Phenyl groups represent Q-2.1 to Q-2.55 groups: R c It is hydrogen. and R d The following are compounds: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-yl-methyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalic acid Ester-3-yl, methyl-2-methylpropionate-3-yl, methyl-2,2-dimethylpropionate-3-yl, ethyl-2-methylpropionate-3-yl, methyl-2-propionate-2-yl, ethyl-2-propionate-2-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetane-3-yl, (3-methyloxetane-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-di Fluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropyl-ethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propyne (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2 -en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptane-2-yl, isobutyl, 1,3-dioxolane-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl and (B) represents one or more compounds having the general formula (II) or their agrochemically acceptable salts. in Q is selected from Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q- 17. Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-29, Q-30, Q-31 and Q-32, The arrows mentioned above The dashed line represents the linking bond between a carbon atom and a Z group. This indicates a linking bond between a carbon atom and a W group; R 1 It is a methyl, ethynyl, 1-propynyl, phenyl, or a five- or six-membered heteroaromatic ring containing one or two nitrogen atoms, wherein the benzene ring and the heteroaromatic ring can be represented by one or two R atoms. 9 Group substitution, R 2 It can be chlorinated, (C1-C3)-alkoxy, (C1-C2)-alkoxy-(C1-C3)-alkoxy, (C1-C2)-fluoroalkoxy, methyl, ethyl, n-propyl, n-butyl, cyclopropyl, or ethynyl. R 3 It can be hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, (C1-C3)-alkoxy, (C1-C3)-fluoroalkyl, (C1-C2)-fluoroalkoxy, (C1-C2)-alkoxy-(C1-C3)-alkoxy, or C1-fluoroalkoxy-(C1-C3)-alkoxy. W is the connection key, CR 4 R 5 , O, NH or N-CH3, Z is the connection key, CR 6 R 7 , O, NH or N-CH3, The condition is that W and Z cannot both be connect keys. Y is O or NR 8 , n1 and n2 are independently 0, 1, 2 or 3, with the condition that n1 + n2 = 2, 3, 4, 5 or 6. R 1Q3 It is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy-(C1-C3)-alkyl, or (C1-C6)-haloalkoxy-(C1-C3)-alkyl. R 2Q3 -(CH2) k -R 3Q3 , Where R 3Q3 Selected from -C(O)NR 5N R 6N -NR 5N R 6N and -S(O)2NR 16N R 17N , And k is 0, 1, or 2. Or R 1Q3 and R 2Q3 Together for -(CH2) nq1 -C(R 4Q3 )R 5Q3 -(CH2) nq2 - where nq1 and nq2 are independently 1 or 2, R 4Q3 It is hydrogen, (C1-C6)-alkyl, hydroxyl, methoxy, or halogen. R 5Q3 Selected from -C(O)NR 5N R 6N -NR 5N R 6N and -S(O)2NR 16N R 17N , Or R 4Q3 and R 5Q3 Together for -(CH2) nq3 -N(R 8 )-(CH2) nq4 - where nq3 and nq4 are independently 1 or 2. R 1Q10 and R 2Q10 Independently selected from hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, and (C1-C3)-alkoxy. Y p Selected from O, CR Y1 R Y2 and NR Y3 , Where R Y1 It is hydrogen or (C1-C4) alkyl. R Y2 It is hydrogen or (C1-C4) alkyl, and R Y3 Selected from hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, -(CO)(C1-C4)-alkyl and -(CO)(C1-C4)-haloalkyl; Y q For N or CH, R 4 R 5 R 6 and R 7 Each of the following is independently a hydrogen, (C1-C5)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C2)-fluoroalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkylthio-(C1-C3)-alkyl, (C1-C3)-alkylsulfinyl-(C1-C3)-alkyl, (C1-C3)-alkylsulfonyl-(C1-C3)-alkyl, (C3-C4)-cycloalkyl, or an unsubstituted 4-, 5-, or 6-membered monocyclic heterocycle, having a cyclic heteroatom selected from oxygen, sulfur, or nitrogen attached to a cyclic carbon atom within the heterocyclic group, under the condition R 4 R 5 R 6 and R 7 No more than one of the following groups is an alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl, or heterocyclic group. Or R 4 and R 5 Together they form -(CH2) n3 -or-(CH2) n4 -X 1 -(CH2) n5 - group and R 6 and R 7 As defined above, Or R 6 and R 7 Together they form -(CH2) n3 -or-(CH2) n4 -X 1 -(CH2) n5 - group and R 4 and R 5 As defined above, Where X 1 For O (oxygen), S (sulfur), S (O), S (O)2, N (R) 8 ), C(H)((C1-C2)-alkyl), C((C1-C2)-alkyl)2 or C(H)((C1-C2)-alkoxy); n3 is 2, 3, 4, or 5. n4 and n5 are independently 1, 2, or 3, provided that n4 + n5 = 2, 3, or 4. Or R 5 and R 6 Together they form -(CH2) n6 -or-(CH2) n7 -C(R 10a (R) 10b )-(CH2) n8 -or-C(R) 10c )=C(R 10d )- group, wherein R 10a It is (C1-C2)-alkyl or (C1-C2)-alkoxy; and R 10b It is hydrogen or (C1-C2)-alkyl, under the condition that R 10a When it is (C1-C2)-alkoxy, R 10b The form is hydrogen, where n6 is 1, 2, or 3, n7 and n8 are independently 0, 1, or 2, provided that n7 + n8 = 0, 1, or 2, and where R 10c and R 10d Independently hydrogen or (C1-C2)-alkyl, R 8 It can be hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, -C(O)(C1-C4)-alkyl, -C(O)(C1-C4)-haloalkyl, or -S(O). n (C1-C6)-alkyl, -S(O) n (C1-C6)-Haloalkyl, -S(O) n -(CH2) n -(C3-C6)-cycloalkyl, -S(O) n C(R 11N )R 12N R 13N -C(O)H, -C(O)-(CH2) n -(C3-C6)-cycloalkyl, -C(O)C(R) 11N )R 12N R 13N -C(O)(C2-C4)-alkenyl, -C(O)(CR 9N R 10N )CN、-C(O)(CR 9N R 10N (CR) 9N R 10N CN, -C(O)CH2C(O)-(C1-C6)-alkyl, -C(O)CH2OC(O)-(C1-C6)-alkyl, -C(O)O(C1-C6)-alkyl, -C(O)O(C1-C6)-haloalkyl, -C(O)(CH2) n S(O) n (C1-C6)-alkyl, -C(O)(C1-C3)-alkoxy-(C1-C6)-alkyl, -C(O)(C1-C3)-alkoxy-(C2-C6)-alkenyl, -C(O)(C1-C3)-alkoxy-(C2-C6)-alkynyl, -C(O)(C1-C3)-alkoxy-(C1-C6)-haloalkyl, -C(O)(C1-C3)-alkoxy-(C3-C6)-cycloalkyl, -C(O)O(C1-C3)-alkoxy-(C1-C6)-alkyl, -C(O)(C1-C3)-alkoxy-(C1-C3)-alkoxy-(C1-C6)-alkyl, -C(O)(CH2) n NR 5N R 6N -C(O)-(CH2) n -NR 7N C(O)R 8N -C(O)-(CH2) n -ON=CR 5N R 5N -CN, -S(O)2NR 16N R1 7N -S(O)(=NR) 18N )R 19N -C(O)C(O)R 20N -C(O)C(R) 23N )=NOR 24N -C(O)C(R) 23N )=N-NR 25N R 26N -(CH2) n -phenyl, -C(O)-(CH2) n -phenyl, -S(O) n -(CH2) n -Phenyl, heterocyclic, -C(O)-(CH2) n -Heterocyclic group, -C(O)(CH2) n -O-(CH2) n -Heterocyclic group, -S(O) n -(CH2) n - Heterocyclic groups, wherein each heterocyclic group is a five- or six-membered heterocyclic ring, which may be aromatic, saturated or partially saturated, and may contain one to four heteroatoms, wherein each heteroatom is independently selected from oxygen, nitrogen and sulfur, and wherein the heterocyclic ring or benzene ring may optionally be substituted by one, two or three substituents independently selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro groups; R 9 This indicates a substituent independently selected from (C1-C4)-alkyl, (C1-C4)-haloalkyl, cyano, and halogen groups; R 5N This indicates substituents independently selected from hydrogen and (C1-C6)-alkyl groups. R 6N The expression indicates that the group is independently selected from hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-haloalkyl, hydroxyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, -(C1-C4)-alkoxy-(C1-C6)-alkyl, -(C1-C3)-alkoxy-(C1-C6)-haloalkyl, -(CR 9N R 10N )-(C1-C6)- haloalkyl, -(CR 9N R 10N )C(O)NR 5N R 5N -C(O)H, -C(O)-(CH2) n -(C3-C6)-cycloalkyl, -C(O)-(CH2) n -C(R 11N )R 12N R 13N Substituents of phenyl and pyridyl, wherein the benzene ring and pyridyl ring are optionally substituted by one, two, or three independent substituents selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano, and nitro; or R 5N and R 6N Together they form -CH2CH2OCH2CH2-; and R 7N Selected from hydrogen and (C1-C6)-alkyl; R 8N The group is selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, phenyl, pyridyl, wherein the benzene ring and pyridyl ring are optionally substituted by 1, 2 or 3 independent substituents selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 9N It can be hydrogen or methyl; R 10N It is hydrogen or methyl; or R 9N and R 10N Together they form -CH2CH2-; and R 11N It can be hydrogen or methyl; R 12N Selected from hydrogen, (C1-C6)-alkyl, hydroxyl, and (C1-C6)-alkoxy; R 13N Selected from hydrogen, (C1-C6)-alkyl, hydroxyl, and (C1-C6)-alkoxy; or R 12N and R 13N Together they form -CH2-X-CH2-; and X is selected from O, S, and NR. 14N ; R 14N Selected from hydrogen, (C1-C3)-alkyl, and (C1-C3)-alkoxy; R 16N It is hydrogen or (C1-C6)-alkyl; and R 17N Selected from hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy-(C1-C3)-alkyl, -C(O)(C1-C6)-alkyl, -C(O)O(C1-C6)-alkyl, and CH2CN; or R 16N and R 17N Together they form -CH2CH2OCH2CH2- and -CH2CH2S(O)2CH2CH2-; R 18N It is hydrogen or (C1-C6)-alkyl; R 19N The group is selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, phenyl, pyridyl, wherein the benzene ring and pyridyl ring are optionally substituted by 1, 2 or 3 independent substituents selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 20N Selected from (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, -NR 21N R 22N , phenyl, pyridyl, wherein the benzene ring and the pyridyl ring may optionally be substituted by one, two or three independent substituents selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 21N The group is selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl and (C1-C6)-haloalkoxy, -C(O)(C1-C6)-alkyl, phenyl, pyridyl, wherein the benzene ring and pyridyl ring may optionally be substituted by 1, 2 or 3 substituents independently selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 22N It is hydrogen or (C1-C6)-alkyl; or R 21N and R 22N Together they form -CH2CH2OCH2CH2-; R 23N Selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy; R 24N The group is selected from hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, -CH2CN, tetrahydropyranyl, phenyl, pyridyl, wherein the benzene ring and pyridyl ring may optionally be substituted by 1, 2 or 3 substituents independently selected from (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halogen, cyano and nitro; R 25N It is hydrogen or (C1-C6)-alkyl; R 26N It is hydrogen or (C1-C6)-alkyl; n can be 0, 1, or 2 independently; G represents hydrogen, a chemically acceptable metal, a chemically acceptable sulfonium group, a chemically acceptable ammonium group, or C(X). 3 )-R 14 -C(X) 4 )-X 5 -R 15 -C(X) 6 )-N(R 16 )-R 17 -SO2-R 18 -P(X) 7 (R) 19 )-R 20 -CH 2 -X 8 -R 21 (C1-C6)-alkoxy-C(O)-CH2-, (C1-C6)-alkoxy-C(O)-CH=CH-, (C2-C7)-en-1-yl-CH2-, (C2-C7)-en-1-yl-CH[(C1-C2)-alkyl]-, (C2-C4)-fluoroen-1-yl-CH2-, (C2-C7)-yn-1-yl-CH2-, (C2-C7)-yn-1-yl-CH[(C1-C2)- The phenyl or heteroaryl group may optionally be independently substituted by one, two, or three substituents selected from (C1-C2)-alkyl, C1-fluoroalkyl, (C1-C2)-alkoxy, C1-fluoroalkoxy, fluorine, chlorine, bromine, cyano, and nitro groups. X 3 X 4 X 5 X 6 X 7 and X 8 Independently, it consists of O (oxygen) and S (sulfur). R 14 For hydrogen, (C1-C 21 )-alkyl, (C2-C 21 )-Alkenyl, (C2-C 18 )-Alkyne group, (C1-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C1-C 10 (C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenyloxy-(C1-C5)-alkyl, (C3-C5)-alkynyloxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)-alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminoalkylene (C1-C5)-alkyl -C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkyl, N-(C1-C5)-alkylcarbonyl-N-(C1-C5)-alkylamino(C1-C5)-alkyl, (C3-C6)-trialkylsilyl-(C1-C5)-alkyl, phenyl-(C1-C5)-alkyl, wherein the phenyl group further Optionally, it may be independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group may also be optionally independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfin ... be independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C3)-alkylsulfinyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group may be independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, The phenyl group is substituted with a sulfonyl group, a (C1-C3)-alkylsulfonyl group, a fluorine group, a chlorine group, a bromine group, a cyano group, or a nitro group; or a (C2-C5)-fluoroalkenyl group, a (C3-C8)-cycloalkyl group; or a phenyl group independently substituted with one, two, or three groups selected from the following groups: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or a heteroaryl group or a heteroaryl group independently substituted with one, two, or three groups selected from the following groups: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro. R 15 For (C1-C 18 )-alkyl, (C3-C 18 )-Alkenyl, (C3-C 18 )-Alkyne group, (C2-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C2-C 10 (C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenyloxy-(C1-C5)-alkyl, (C3-C5)-alkynyloxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)-alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminoalkylene (C1-C5)-alkyl -C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkyl, N-(C1-C5)-alkylcarbonyl-N-(C1-C5)-alkylamino(C1-C5)-alkyl, (C3-C6)-trialkylsilyl-(C1-C5)-alkyl, phenyl-(C1-C5)-alkyl, wherein the phenyl group further Optionally, it may be independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group may also be optionally independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfin ... be independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C3)-alkylsulfinyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group may be independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, The phenyl group is substituted with a sulfonyl group, a (C1-C3)-alkylsulfonyl group, a fluorine group, a chlorine group, a bromine group, a cyano group, or a nitro group; or a (C2-C5)-fluoroalkenyl group, a (C3-C8)-cycloalkyl group; or a phenyl group independently substituted with one, two, or three groups selected from the following groups: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or a heteroaryl group or a heteroaryl group independently substituted with one, two, or three groups selected from the following groups: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro. R 16 and R 17 Independently hydrogen, (C1-C 10 )-alkyl, (C2-C 10 )-Alkenyl, (C2-C 10 )-Alkyne group, (C2-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C1-C 10 (C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenoxy-(C1-C5)-alkyl, (C3-C5)-alkynoxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)- Alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminooxy-(C1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl-(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkane The phenyl group may optionally be independently surrounded by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C5)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfinyl, etc. The heteroaryl group is substituted with an acyl, fluorine, chlorine, bromine, cyano, or nitro group, and is (C1-C5)-alkyl, wherein the heteroaryl group is optionally and independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, or nitro groups, or (C2-C5)-fluoroalkenyl or (C3-C8)-cycloalkyl.A phenyl group, or a phenyl group independently substituted with one, two, or three groups selected from the following: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or a heteroaryl group, or a heteroaryl group independently substituted with one, two, or three groups selected from the following: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkyl, (C1-C3)-fluoro ... -C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or heteroarylamino or heteroarylamino, wherein the heteroaryl group is independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or diarylamino or diarylamino, wherein each heteroaryl group is independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or diarylamino, or diarylamino, wherein each heteroaryl group is independently substituted by 1, 2 or 3 groups selected from (C1-C3)-fluoroalkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy ...3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkyl, fluorine, chlorine, bromine, cyano, nitro, or diary (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, or phenylamino or phenylamino groups, wherein the corresponding phenyl group is independently replaced by 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano The phenyl group is substituted with a nitro group, or a diphenylamino or diphenylamino group, wherein each phenyl group is independently substituted with one, two or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, or (C3-C7)-cycloalkylamino, di-[(C3-C7)-cycloalkyl]amino, (C3-C7)-cycloalkoxy; or; R 16 and R 17 Together with the nitrogen atoms they are attached to, they form an unsubstituted 4- to 7-membered ring, which may optionally contain heteroatoms from O (oxygen) and S (sulfur). R 18 For (C1-C 10 )-alkyl, (C2-C 10 )-Alkenyl, (C2-C 10 )-Alkyne group, (C1-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C1-C 10 (C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenoxy-(C1-C5)-alkyl, (C3-C5)-alkynoxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)- Alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminooxy-(C1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl-(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkane The phenyl group is further optionally and independently surrounded by one, two or three groups selected from (C1-C3)-alkyl, (C1-C5)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1-C3)-alkylsulfonyl, etc. The heteroaryl group is substituted with a group of alkyl, fluorine, chlorine, bromine, cyano, or nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is optionally independently substituted by 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, or nitro, or (C2-C5)-fluoroalkenyl or (C3-C8)-cycloalkyl.A phenyl group, or a phenyl group independently substituted with one, two, or three groups selected from the following groups: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or a heteroaryl group, or a heteroaryl group independently substituted with one, two, or three groups selected from the following groups: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkyl ... - A fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or a heteroarylamino or heteroarylamino group, wherein the heteroaryl group is independently substituted by 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or a diarylamino or diarylamino group, wherein each heteroaryl group is independently substituted by 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or a diarylamino or diarylamino group. (C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, or phenylamino or phenylamino, wherein the corresponding phenyl group is independently replaced by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups. The phenyl group is substituted with a group, or diphenylamino or diphenylamino, wherein each phenyl group is independently substituted with one, two or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or (C3-C7)-cycloalkylamino, di-[(C3-C7)-cycloalkyl]amino, (C3-C7)-cycloalkoxy, (C1-C; 10 )-alkoxy, (C1-C 10 (C3-C7)-fluoroalkoxy, (C3-C7)-alkylamino, di-[(C3-C7)-alkyl]amino; R 19 and R 20 Independently for (C1-C) 10 )-alkyl, (C2-C 10 )-Alkenyl, (C2-C 10 )-Alkyne group, (C1-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C1-C 10 (C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenoxy-(C1-C5)-alkyl, (C3-C5)-alkynoxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)- Alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkylaminooxy-(C1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl-(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkane The phenyl group is further optionally and independently surrounded by one, two or three groups selected from (C1-C3)-alkyl, (C1-C5)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1-C3)-alkylsulfonyl, etc. The heteroaryl group is substituted with a group of alkyl, fluorine, chlorine, bromine, cyano, or nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is optionally independently substituted by 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, or nitro, or (C2-C5)-fluoroalkenyl or (C3-C8)-cycloalkyl.A phenyl group, or a phenyl group independently substituted with one, two, or three groups selected from the following: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or a heteroaryl group, or a heteroaryl group independently substituted with one, two, or three groups selected from the following: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, ... Bromine, cyano, nitro, or heteroarylamino, or heteroarylamino, wherein the heteroaryl group is independently substituted by 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or diarylamino, or diarylamino, wherein each heteroaryl group is independently substituted by 1, 2, or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoro ... -C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, or phenylamino or phenylamino, wherein the corresponding phenyl group is independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, or diphenylamino or diphenylamino, wherein each ...fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, or diphenylamino or diphenylamino, wherein each phenyl group is independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C3)-fluoroalkyl, fluorine, chlorine, bromine, cyano, nitro groups, or diphenylamino or diphenylamino, wherein each phenyl group is independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C3)-fluoroalkyl, (C1-C3)-fluoroalkyl, fluorine, chlorine, bromine, cyano, nitro groups, or diphenylamino groups. (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, or benzyloxy and phenyloxy groups, wherein the corresponding phenyl groups are optionally independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro groups, and; R 21 For (C1-C 10 )-alkyl, (C3-C 10 )-Alkenyl, (C3-C 10 )-Alkyne group, (C1-C 10 )-Fluoroalkyl, (C1-C 10 )-cyanoalkyl, (C1-C 10 )-nitroalkyl, (C2-C 10 (C1-C5)-aminoalkyl, (C1-C5)-alkylamino, (C2-C8)-dialkylamino, (C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C3-C5)-alkenoxy-(C1-C5)-alkyl, (C3-C5)-alkynoxy-(C1-C5)-alkyl, (C1-C5)-alkylthio-(C1-C5)-alkyl, (C1-C5)-alkylsulfinyl-(C1-C5)-alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-aminoalkyl, (C1-C5)-alkylamino-(C1-C5)-alkyl, (C2-C8)-dialkylamino-(C1-C5)-alkyl, (C3-C7)-cycloalkyl-(C1-C5)-alkyl, (C1-C5)-alkoxy-(C1-C5)-alkyl, (C2-C8)-alkyl-dialkylamino-(C1-C5)-alkyl, (C1-C5)-alkylsulfonyl-(C1-C5)-alkyl, (C2-C8)-alkyl-dialkylamino-(C1-C5)-alkyl, (C1-C5)- ... (C1-C5)-alkyleneaminooxy-(C1-C5)-alkyl, (C1-C5)-alkylcarbonyl-(C1-C5)-alkyl, (C1-C5)-alkoxycarbonyl-(C1-C5)-alkyl, aminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylaminocarbonyl-(C1-C5)-alkyl, (C2-C8)-dialkylaminocarbonyl-(C1-C5)-alkyl, (C1-C5)-alkylcarbonylamino-(C1-C5)-alkyl, N-(C1-C5)-alkylcarbonyl-N-(C1-C5)-alkylamino(C1-C5)-alkyl, (C3-C6)-trialkylsilyl-(C1-C5)-alkyl, phenyl -(C1-C5-alkyl, wherein the phenyl group is optionally and independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is optionally and independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkyl ... or heteroaryl-(C1-C5)-alkyl, wherein the heteroaryl group is optionally and independently substituted by 1, 2 or 3 groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, fluorine, chlorine, chloroalkyl, bromine, cyano, nitro, or heteroaryl-(C1-C5)-alkyl, or heteroaryl-(C1-C5)-alkyl, fluorine, chloroalkyl, fluorine, chloroalkyl, fluorine, chloroalkyl, fluorine, chloroalkyl, fluorine, chloroalkyl, fluorine The phenyl group is substituted with a group selected from (C1-C3)-alkoxy, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or phenoxy-(C1-C5)-alkyl, wherein the phenyl group is optionally independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkoxy, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or heteroaryloxy-(C1-C5)-alkyl.The heteroaryl group is optionally and independently substituted by one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, fluorine, chlorine, bromine, cyano, nitro, or phenyl, or phenyl independently substituted by one, two, or three groups selected from: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkyl. The aryl group may be oxy, fluorine, chlorine, bromine, cyano, nitro, or heteroaryl, or independently substituted with one, two, or three groups selected from the following: (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, or phenyl-C(=O), wherein the phenyl group is optionally further independently substituted with one, two, or three groups selected from (C1-C3)-alkyl, (C1-C3)-fluoroalkyl, (C1-C2)-alkoxy, (C1-C3)-fluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro.
2. The herbicide / safener combination according to claim 1, comprising one or more safeners selected from compounds A1, A2, A3, A4, A5, A6, A7, A8, A9, and A10 as compound (A), wherein... A1 = {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl acetate A2 = {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid A3 = {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl acetate A4 = {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid A5 = {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl acetate A6 = {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid A7 = {[5-(4-bromo-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl acetate A8 = {[5-(4-bromo-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid A9 = {[1-(4-bromo-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}methoxyethyl acetate A10 = {[1-(4-bromo-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid 。 3. The herbicide / safety agent combination according to claim 2, wherein (A) is selected from A1, A3, A5, A7 and A9.
4. The herbicide / safener combination according to any one of claims 1 to 3, wherein (B) represents one or more compounds having general formula (II) or an agriculturally chemically acceptable salt thereof, wherein: Q is a Q-1 group. R 1 It is a methyl, 1-propynyl, or a six-membered heteroaromatic ring containing one or two nitrogen atoms, wherein the heteroaromatic ring can be represented by an R 9 Group substitution, R 2 It is chlorine, methoxy, methyl, or ethyl. R 3 It is chlorine, methyl, or ethyl. W can be CH2, O, NH, or N-CH3. Y is O or NR 8 , Z stands for linker or CH2. n1 and n2 are independently 1 or 2, provided that n1 + n2 = 2, 3, or 4. R 8 It can be (C1-C4)-alkoxy, -C(O)(C1-C4)-alkyl, -C(O)-(C3-C6)-cycloalkyl, or -C(O)O(C1-C6)-alkyl. -S(O)2NHR1 7N ,-S(O)(=NH)R 19N ,-C(O)C(O)R 20N ,-C(O)C(R 23N )=N-O-R 24N ; R 9 It is either cyano or halogen; R 17N It is methyl or ethyl; R 19N It is methyl or ethyl; R 20N Methyl, ethyl or -NHR 22N ; R 22N N is methyl or ethyl; R 23N It is methyl or ethyl; R 24N It is methyl or ethyl; G represents hydrogen, an agriculturally acceptable metal, or C(O)-R. 14 or -C(O)-OR 15 , R 14 It is (C1-C6)-alkyl. R 15 It is (C1-C6)-alkyl.
5. The herbicide / safener combination according to claim 4, wherein Q is Q-1, and R 1 R 2 R 3 The following definitions apply to W, Y, Z, and G, as well as n1 and n2: 。 6. The herbicide / safener combination according to any one of claims 1 to 3, wherein (B) represents one or more compounds having general formula (II) or an agriculturally chemically acceptable salt thereof, wherein: Q is a Q-2 group. R 1 It is 1-propynyl. R 2 It is chlorine, methoxy, methyl, or ethyl. R 3 It is chlorine, methyl, or ethyl. W can be CH2, O, NH, or N-CH3. Y is NR 8 , Z stands for linker or CH2. n1 is 2, R 8 It is (C1-C4)-alkoxy, -C(O)(C1-C4)-alkyl, -C(O)-(C3-C6)-cycloalkyl or -S(O)2C(R 11N )R 12N R 13N ; R 11N It is hydrogen; R 12N It is hydrogen; R 13N It is methyl; G is hydrogen, a metal acceptable in agricultural chemistry, C(O)-R 14 or -C(O)-OR 15 , R 14 It is (C1-C6)-alkyl. R 15 It is (C1-C6)-alkyl.
7. The herbicide / safener combination according to claim 6, wherein Q is Q-2, and Y and G have the following definitions, and wherein R 1 It is 1-propynyl, R 2 and R 3 Each is a methyl group, and W and Z are both CH2, and n1 is 2: 。 8. The herbicide / safener combination according to any one of claims 1 to 3, wherein (B) represents one or more compounds having general formula (II) or an agriculturally chemically acceptable salt thereof, wherein: Q is the Q-3 group. R 1 It is 1-propynyl. R 2 It is chlorine, methoxy, methyl, or ethyl. R 3 It is chlorine, methyl, or ethyl. W can be CH2, O, NH, or N-CH3. Z stands for linker or CH2. R 1Q3 It is hydrogen or (C1-C6)-alkyl. R 2Q3 -(CH2) k -R 3Q3 , Where R 3Q3 Selected from -C(O)NR 5N R 6N -NR 5N R 6N and -S(O)2NR 16N R 17N , And k is 0, Or R 1Q3 and R 2Q3 Together for -(CH2) nq1 -C(R 4Q3 R 5Q3 -(CH2) nq2 -where nq1 and nq2 are independently 1 or 2, R 4Q3 It is hydrogen or (C1-C6)-alkyl. R 5Q3 Selected from -C(O)NR 5N R 6N -NR 5N R 6N and -S(O)2NR 16N R 17N , Or R 4Q3 and R 5Q3 Together as -(CH2)-N(R) 8 )-(CH2)-, R 8 It is (C1-C4)-alkoxy, -C(O)(C1-C4)-alkyl, -C(O)-(C3-C6)-cycloalkyl or -S(O)2C(R 11N )R 12N R 13N ; R 5N This indicates substituents independently selected from hydrogen and (C1-C6)-alkyl groups. R 6N This indicates that the components are independently selected from hydrogen, (C1-C6)-alkyl, and -C(O)-C(R). 11N )R 12N R 13N Substituents, R 11N It is hydrogen; R 12N It is hydrogen; R 13N It can be hydrogen or methyl; R 16N It is hydrogen or (C1-C6)-alkyl; R1 7N It is hydrogen or (C1-C6)-alkyl; G represents hydrogen, an agriculturally acceptable metal, or C(O)-R. 14 or -C(O)-OR 15 , R 14 It is (C1-C6)-alkyl. R 15 It is (C1-C6)-alkyl.
9. The herbicide / safener combination according to claim 8, wherein Q is Q-3, and G has the following definition, and wherein R 1 It is 1-propynyl, R 2 and R 3 Each is a methyl group, W and Z are each CH2 groups, and R 1Q3 It is hydrogen, and R 2Q3 -C(O)NR 5N R 6N , where R 5N and R 6N Each is a methyl group: 。 10. The herbicide / safener combination according to claim 8, wherein Q is Q-3, and R 5Q3 The definitions of R and G are as follows, and R is a subset of G. 1 It is 1-propynyl, R 2 and R 3 Each is a methyl group, and W and Z are each CH2, and R is... 1Q3 and R 2Q3 The groups together form -(CH2). nq1 -C(R 4Q3 )R 5Q3 -(CH2) nq2 - where nq1 and nq2 are each 2, and R 4Q3 For hydrogen: 。 11. The herbicide / safener combination according to claim 8, wherein Q is Q-3, and G has the following definition, and wherein R 1 It is 1-propynyl, R 2 and R 3 Each is a methyl group, and W and Z are each CH2, and R is... 1Q3 and R 2Q3 The groups together form -(CH2). nq1 -C(R 4Q3 )R 5Q3 -(CH2) nq2 - where nq1 and nq2 are each 1, R 4Q3 and R 5Q3 The groups together form -(CH2)-N(R) 8 )-(CH2)-, and where R 8 -(CO)CH3: 。 12. The herbicide / safener combination according to claim 5, wherein (A) is A3 = {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl acetate, and (B) is selected from B1-6, B1-38, B1-42, B1-46, B1-66 and B1-68.
13. The herbicide / safener combination according to any one of claims 1 to 12, further comprising one or more conventional additives for crop protection.
14. A method for protecting crop plants from the phytotoxic side effects of herbicide (B), characterized in that, An effective amount of a safener (A) is applied to plants, plant parts, plant seeds, or cultivated areas before, during, or simultaneously with the application of herbicide (B), wherein the combination of herbicide (B) and safener (A) is as described in any one of claims 1 to 12. Preferably, the crop is a cereal plant, and / or The herbicide (B) is preferably applied at a rate of 40 to 200 g / ha of active substance, and the weight ratio of safener (A) to herbicide (B) is 1:400 to 500:
1.
15. The use of the herbicide / safener combination according to any one of claims 1 to 13 for controlling harmful plants or for regulating plant growth.
Citation Information
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