MXPA01001768A - Methoximinophenylacetic acid amides - Google Patents
Methoximinophenylacetic acid amidesInfo
- Publication number
- MXPA01001768A MXPA01001768A MXPA/A/2001/001768A MXPA01001768A MXPA01001768A MX PA01001768 A MXPA01001768 A MX PA01001768A MX PA01001768 A MXPA01001768 A MX PA01001768A MX PA01001768 A MXPA01001768 A MX PA01001768A
- Authority
- MX
- Mexico
- Prior art keywords
- methyl
- ethyl
- carbon atoms
- butyl
- propyl
- Prior art date
Links
- KJWAJDLVKYQCLZ-UHFFFAOYSA-N 2-methoxyimino-2-phenylacetamide Chemical class CON=C(C(N)=O)C1=CC=CC=C1 KJWAJDLVKYQCLZ-UHFFFAOYSA-N 0.000 title abstract description 5
- -1 alkoxycarbonylthio Chemical group 0.000 claims abstract description 517
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 48
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 38
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 20
- 150000001408 amides Chemical class 0.000 claims abstract description 12
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims abstract description 5
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 198
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 175
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 134
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 115
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 110
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 106
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 103
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 101
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 150000001875 compounds Chemical class 0.000 claims description 77
- 239000011737 fluorine Substances 0.000 claims description 67
- 229910052731 fluorine Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 62
- 239000000460 chlorine Substances 0.000 claims description 59
- 229910052801 chlorine Inorganic materials 0.000 claims description 59
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 52
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 50
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 44
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 44
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical group CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 38
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 36
- 239000001301 oxygen Substances 0.000 claims description 34
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 34
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
- 150000002829 nitrogen Chemical group 0.000 claims description 27
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- 239000011593 sulfur Substances 0.000 claims description 26
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 26
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M isothiocyanate Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- IBAHLNWTOIHLKE-UHFFFAOYSA-N cyano cyanate Chemical group N#COC#N IBAHLNWTOIHLKE-UHFFFAOYSA-N 0.000 claims description 13
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 13
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 12
- 125000004434 sulfur atoms Chemical group 0.000 claims description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 10
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 10
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000005842 heteroatoms Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- QKCJLRBNOGBAIY-UHFFFAOYSA-N (Z)-2-methylbut-2-ene Chemical group C[CH]C(C)=C QKCJLRBNOGBAIY-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- TZFVGECPKMMFQA-UHFFFAOYSA-N 2-methanidylprop-2-enoxymethylidyneoxidanium Chemical group [CH2-]C(=C)COC#[O+] TZFVGECPKMMFQA-UHFFFAOYSA-N 0.000 claims description 4
- ZEKBKTMMBLWNGK-UHFFFAOYSA-N 5-tert-butyl-2H-tetrazole Chemical class CC(C)(C)C=1N=NNN=1 ZEKBKTMMBLWNGK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- MDQRDWAGHRLBPA-UHFFFAOYSA-N Fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000004429 atoms Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000006351 ethylthiomethyl group Chemical compound [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- XOBKSJJDNFUZPF-UHFFFAOYSA-N methoxyethyl Chemical group CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 4
- 125000006533 methyl amino methyl group Chemical compound [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004372 methylthioethyl group Chemical compound [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004092 methylthiomethyl group Chemical compound [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000006222 dimethylaminomethyl group Chemical compound [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
- WGSMVIHKBMAWRN-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1-benzofuran Chemical compound C1C=CC=C2OCCC21 WGSMVIHKBMAWRN-UHFFFAOYSA-N 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N Propadiene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N isocyanate Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 29
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 241000607479 Yersinia pestis Species 0.000 claims 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Ethylene tetrachloride Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims 1
- 101710027641 PPARGC1B Proteins 0.000 claims 1
- 241000269799 Perca fluviatilis Species 0.000 claims 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N Phenazone Chemical class CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
- 229960005222 phenazone Drugs 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000000855 fungicidal Effects 0.000 abstract description 8
- 239000000417 fungicide Substances 0.000 abstract description 6
- 241000196324 Embryophyta Species 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 37
- 230000000694 effects Effects 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 150000002431 hydrogen Chemical class 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- 239000003995 emulsifying agent Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000002877 alkyl aryl group Chemical group 0.000 description 11
- 238000011081 inoculation Methods 0.000 description 11
- 229920000151 polyglycol Polymers 0.000 description 11
- 239000010695 polyglycol Substances 0.000 description 11
- 125000003944 tolyl group Chemical group 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 230000001681 protective Effects 0.000 description 9
- 230000001012 protector Effects 0.000 description 9
- 239000000725 suspension Substances 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 6
- 210000004215 spores Anatomy 0.000 description 6
- ISFFCSPHFNWPST-UHFFFAOYSA-N 2-methoxyimino-2-phenylacetic acid Chemical compound CON=C(C(O)=O)C1=CC=CC=C1 ISFFCSPHFNWPST-UHFFFAOYSA-N 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 241000221787 Erysiphe Species 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 241000233626 Plasmopara Species 0.000 description 4
- 206010037888 Rash pustular Diseases 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 240000007119 Malus pumila Species 0.000 description 3
- 235000011430 Malus pumila Nutrition 0.000 description 3
- 235000015103 Malus silvestris Nutrition 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 3
- 240000008529 Triticum aestivum Species 0.000 description 3
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 238000004166 bioassay Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000012439 solid excipient Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000021307 wheat Nutrition 0.000 description 3
- KAATUXNTWXVJKI-WSTZPKSXSA-N (1S)-cis-(alphaR)-cypermethrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-WSTZPKSXSA-N 0.000 description 2
- RLLPVAHGXHCWKJ-HKUYNNGSSA-N (3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-HKUYNNGSSA-N 0.000 description 2
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);N-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N κ-bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N τ-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
Abstract
The invention relates to new methoximinophenylacetic acid amides of formula (I), wherein R represents alkylthio, halogenalkylthio, optionally substituted arylthio, alkoxycarbonylthio, alkylthiocarbonyl, -S-Y, -S-N(R1R2), -CO-N(R3R4), -CN, -CH2-O-R5, -PO(OR6)R7, -PS(OR6)R7 and A, O, W, Y, Z, L1-L4 and R1-R7 have the meaning given in the description. The invention also relates to a method for preparing said amides and for using them as fungicides.
Description
AMIDAS OF METOXMNOFENILACTIC ACID. FIELD OF THE INVENTION The invention relates to novel amides of methoximinophenylacetic acid, to a process for their preparation and to their use as fungicides. DESCRIPTION OF THE PRIOR ART It has already been known that certain compounds, which are similar from the point of view of their constitution to those described below, have fungicidal properties (see, for example, EP-A-398 692, EP-A-528 681, WO 97/00856). The fungicidal effect of these compounds, however, leaves much to be desired, especially at low application rates. DETAILED DESCRIPTION OF THE INVENTION The new amides of methoximinophenylacetic acid of the general formula (I) have now been found,
wherein A means hydrogen, alkoxycarbonyl, methyl, ethyl or cyclopropyl, or has the same meaning as R, R means alkylthio, haloalkylthio, arylthio, optionally substituted, alkoxycarbonylthio, alkylthiocarbonyl, -SY, -SN (R'R2) , -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies alkyl,
Ref: 126980 R2 means alkyl, alkoxycarbonyl, or together with R1 as well as with the nitrogen atom, to which they are linked, means a substituted heterocyclic ring, R3 signifies alkyl or aryl if appropriate, R4 signifies alkylthio, alkylsulfonyl or haloalkylthio or together with R3, as well as with the nitrogen atom, with which they are bound, means a substituted heterocyclic ring if appropriate, R5 means alkyl, R6 signifies alkyl, R7 signifies alkyl, alkoxy or alkylamino, Y means same group which is already linked to the S- atom, or, when A means methyl, R also means alkylcarbonyl, alkoxycarbonyl, halogenoalkoxycarbonyl, alkoxycarbonylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl or substituted arylsulfonyl, if appropriate, G means a single bond, means Oxygen, sulfur or means alkanediyl, alkenodiyl, alkynediyl substituted In this case, halogen, hydroxy, alkyl, haloalkyl or cycloalkyl, means one of the following groupings, in which the left side is linked respectively to Z: -Q-CQ-, -CQ-Q-, -CH2-Q-; -Q-CH2-, -CQ-Q-CH2, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH2-, -N = N-, S (O) n -, -CH2-S (O) n-, -CQ-, -S (O) n -CH2-, -C (R8) = NO-, -N (R9) -, -CQ-N (R9) - , -N (R9) -CQ-, -Q-CQ-N (R9) -, -N = C (R8) -Q-CH2-, -CH (R8) -ON = CH-, -C (R8) = NN = CH-, -NO ^ -CQ-Q-, -N (R9) -C (R8) = NO-CH2-, -O-CH2-C (R8) = NO-CH2-, -N = NC (R8) = NO-CH2-, -C (= NO-RI0) -C (R8) = NO-CH2-, _c (= NO-R10) -C (R8) -ON = CH-, -C (= NO-R10) -C (R8) = NN = CH-, -C (= NO-R10) -C (R8) -ON = C (CH3) -, -T-Ar1- or T-Ar'-Q- wherein Ar 1 means arylene, heteroarylene, cycloalkylene or heterocycloalkylene substituted if appropriate (ie a double-linked aliphatic ring, in which one or several carbon atoms are replaced by heteroatoms, ie by atoms that are different from carbon), means the numbers 0, 1 or 2, Q oxygen or sulfur, R8 means hydrogen, cyano, or means alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl respectively substituted, R9 means hydrogen ene, hydroxy, cyano or means optionally substituted alkyl, alkoxy or cycloalkyl, R10 respectively means hydrogen, alkyl or benzyl substituted and T means a single bond, means oxygen, sulfur, -CH2-O-, -CH2- S- or means substituted alkanediyl, if appropriate, L1, L2, L and L4 are the same or different and independently of each other denote hydrogen, halogen or alkyl, W means hydrogen, fluorine, cyano or thiocyanate and Z means alkyl, alkenyl , substituted alkynyl, cycloalkyl, aryl or heterocyclyl, respectively, if appropriate. In the definitions the saturated or unsaturated hydrocarbon chains, such as alkyl, even in combination with heteroatoms, such as alkoxy, alkylthio, are, respectively, straight chain or branched chain. Halogenoalkyl means partially or fully halogenated alkyl. In the case of polyhalogenated haloalkyl, the halogen atoms may be the same or different. Preferred halogen atoms are fluorine and chlorine and especially fluorine. If the haloalkyl also carries other substituents, the maximum possible number of halogen atoms is reduced to the remaining free valencies. In general halogen means fluorine, chlorine, bromine or iodine, preferably means fluorine, chlorine or bromine, especially fluorine or chlorine. Heterocyclyl means saturated or unsaturated, as well as aromatic, ring compounds, in which at least one ring atom is a heteroatom, that is to say a non-carbon atom. If the ring has several heteroatoms, these may be the same or different. Preferred heteroatoms are oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, they are not contiguous. If necessary, the ring compounds form with other carbocyclic or heterocyclic, fused or bridged rings, together a polycyclic ring system. A polycyclic ring system can be linked through the heterocyclic ring or a condensed carbocyclic ring. Monocyclic or bicyclic ring systems are preferred, especially monocyclic or bicyclic, aromatic ring systems. It has also been found that the novel amines of methoxyiminophenylacetic acid of the general formula (I) are obtained if amides of the formula (II) are reacted
wherein A, G, L1, L2, L3, L4, W and Z have the meanings indicated above, with an electrophilic reagent of the formula (III), RX (III) in which R has the meaning indicated above, and X means a dissociable group, if appropriate in the presence of a diluent and, if appropriate, in the presence of a base.
Finally, it has been found that the new amides of methoximinophenylacetic acid of the general formula (I) show a very potent fungicidal activity. The compounds according to the invention can optionally be present as mixtures of the various possible isomeric forms, in particular of the stereoisomers, such as, for example, the E and Z isomers or optical isomers. Both the E isomers and the Z isomers, the individual enantiomers, the racemates, as well as any mixture of these isomers are claimed. The subject of the present application are preferably methoximinophenylacetic acid amides of the formula (I), wherein A means hydrogen, methyl, ethoxycarbonyl, ethyl or cyclopropyl or has the same meaning as R, means alkylthio, haloalkylthio, alkoxycarbonylthio, alkylthiocarbonyl, with respectively 1 to 4 carbon atoms in the alkyl, phenylthio groups optionally substituted by halogen, cyano, alkyl, alkoxy or alkoxycarbonyl with 1 to 4 carbon atoms, haloalkyl or haloalkoxy with 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms, -SY-, -SN (R'R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7. R1 means alkyl with 1 to 4 carbon atoms, R2 means alkyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to
4 carbon atoms in the alkyl part, or together with R 1, as well as with the nitrogen atom, with which they are bound, means a heterocyclic ring with 5 or 6 members in the ring, optionally substituted by methyl or ethyl R3 means alkyl having 1 to 4 carbon atoms or phenyl optionally substituted by halogen, by alkyl or by alkoxy with 1 to 6 carbon atoms, by haloalkyl or by haloalkoxy with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, R 4 means alkylthio or alkylsulfonyl with 1 to 4 carbon atoms or halogenalkylthio having 1 to 4 carbon atoms and 1 to 5 same or different halogen atoms or together with R 3, as well as with the atom of nitrogen, to which they are linked, means a heterocyclic ring with 5 or 6 members in the ring, optionally substituted by methyl or ethyl, R5 means alkyl with 1 to 4 carbon atoms, R6 sig it means alkyl with 1 to 4 carbon atoms, R7 means alkyl, alkoxy or alkylamino with 1 to 4 carbon atoms in the alkyl chains, Y means the same group which is already bonded to the sulfur atom, j! or, when A means methyl, R also denotes alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylcarbonyl, halogenoalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl with 1 to 4 carbon atoms in the alkyl or phenylsulfonyl chains optionally substituted by alkyl with 1 to 4 carbon atoms. carbon, G means a single bond, means oxygen, sulfur or means alkanediyl, alkenodiyl, alkynediyl, with respectively up to 4 carbon atoms, substituted, if appropriate by halogen, by hydroxy, by alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms or for cycloalkyl with 3 to 6 carbon atoms means one of the following groupings, in which the left side is linked respectively with Z: -Q-CQ-, -CQ-Q-, - CH2-Q-; -Q-CH2-, -CQ-Q-CH2, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH2-, -N = N-, S (O) n -, -CH2-S (O) n-, -CQ-, -S (O) n -CH2-, -C (R8) = NO-, -C (R8) = NO-CH2-, -N (R9) ) -, -CQ-N (R9) -,
-N = N-C (R8) = N-O-CH2-, -C (= N-O-R10) -C (R8) = N-O-CH2-, -C (= NO-R10) -C (R8) -ON = CH-, -C (= NO-R10) -C (R8) = NN = CH-, -C (= NO-R10) -C ( R8) -ON = C (CH3) -, -T-Ar1- or T-Ar'-Q-, where n means the numbers 0, 1 or 2, Q means oxygen or sulfur, R8 means hydrogen, cyano, means alkyl , alkoxy, alkylthio, alkylamino or dialkylamino with respectively 1 to 6 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms, or means cycloalkyl with 3 to 6 atoms carbon atoms substituted, where appropriate, by halogen, cyano, carboxy, alkyl with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms, and R9 means hydrogen, hydroxy, cyano, or means alkyl with 1 to 6 carbon atoms optionally substituted by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms, or by cycloalkyl having 3 to 6 carbon atoms, optionally substituted by halogen, by cyano, by carboxy, by alkyl having 1 to 4 carbon atoms or by alkoxycarbonyl having 1 to 4 carbon atoms, R 10 is hydrogen, alkyl having 1 to 4 carbon atoms or benzyl optionally substituted by halogen, alkyl or alkoxy respectively 1 to 6 carbon atoms, by haloalkyl or by haloalkoxy with respectively 1 to 6 carbon atoms and 1 to 13 same or different halogen atoms, T means a single bond, means oxygen, sulfur, -CH2-O-, -CH2 -S- or means alkanediyl having 1 to 3 carbon atoms, means phenylene, naphthylene, cycloalkylene respectively substituted one or more times, in the same or different forms, or means heteroarylenes or heterocycloalkylenes having 3 to 7 members in the ring, one of which being at least oxygen, sulfur or nitrogen and, if desired, one or two more nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl respectively straight-chain or branched chain, with respectively 1 to 6 carbon atoms, alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having respectively 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, respectively straight-chain or branched chain, each having 1 to 6 carbon atoms in the individual alkyl portions, as well as; cycloalkyl with 3 to 6 carbon atoms. L1, L2, L3 and L4 are the same or different and independently of one another denote hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or n- or i-propyl, n-, i-, s- or t-butyl , W means hydrogen, fluorine, cyano or thiocyanate and Z means alkyl having 1 to 8 carbon atoms, optionally substituted one or more times, in the same or different ways by halogen, cyano, hydroxy, amino, alkoxy with 1 to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for alkylsulfamyl with 1 to 4 carbon atoms
0 for alkylsulfonyl having 1 to 4 carbon atoms (which may be substituted, if appropriate, by halogen); means alkenyl or alkynyl with respectively up to 8 carbon atoms, respectively substituted, if appropriate, by halogen; tetrahydropyranyl; means cycloalkyl with 3 to 6 carbon atoms, each optionally substituted one or more times, in the same or different manner by halogen, by cyano, by carboxy, by phenyl (which is optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms), by alkyl with 1 to 4 carbon atoms or by alkoxycarbonyl with
1 to 4 carbon atoms; means phenyl, naphthyl, tetrahydrobenzofuran respectively substituted one or more times, in the same or different forms or means heterocyclyl with 3 to 7 members in the ring, one of which being at least oxygen, sulfur or nitrogen and in case given one or two more are nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; formyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl respectively straight-chain or branched chain with 1 to 6 carbon atoms respectively; substituted t-butyl tetrazole; alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having respectively 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; phenyl; halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulfonyloxy respectively straight-chain or branched chain with respectively 1 to 6 carbon atoms in the individual alkyl portions; alkylene or dioxyalkylene having respectively 1 to 6 carbon atoms, respectively doubly linked, each optionally substituted one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl with 1 to 4 carbon atoms and / or straight chain or branched chain halogen alkyl with 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms; cycloalkyl with 3 to 6 carbon atoms; heterocyclyl or heterocyclylmethyl with respectively 3 to 7 members in the ring, 1 to 3 of which, respectively, are the same or different heteroatoms -especially nitrogen, oxygen and / or sulfur-, or a group
A'- \ _ j 'N O "
where A means alkyl with 1 to 4 carbon atoms or cycloalkyl with 1 to 6 carbon atoms and A2 means alkyl with 1 to 4 carbon atoms, alkenyl or alkynyl with 2 to 4 carbon atoms, optionally substituted by cyano , by alkoxy, by alkylthio, by alkylamino, by dialkylamino or by phenyl. The present application relates especially to the amides of the methoximinophenylacetic acid of the formula (I), in which A means hydrogen, methyl, ethoxycarbonyl, ethyl or cyclopropyl, or has the same meaning as R, means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, tichloromethylthio, 2,2,2-trifluoroethylthio, 1,1-difluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n - or i-propylthiocarbonyl, phenylthio substituted, if appropriate, one to three times, fluorine, chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propylthio, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methoxycarbonyl or ethoxycarbonyl, -SY, -SN (R! R2), -CO-N (R3R4), -CN, -CH2-O- R5, -PO (OR6) R7, -PS (OR6) R7, where R1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1 as well as with the nitrogen atom, with which they are bound, means pyrrolidino, piperidino, or morpholino substituted in In the case given by methyl or ethyl, R3 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or phenyl, optionally substituted one to three times by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- i-propoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methoxycarbonyl or ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R3, as well as with the nitrogen atom, with which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group that is already linked to the sulfur atom, or, when A s methyl, R means also acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, i-butoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl, G stands for oxygen or means dimethylene (ethane-1,2-diyl) ), ethene-1, 2-diyl, respectively substituted, if appropriate, by fluorine, chlorine or bromine or means one of the following groupings, in which the left side is linked respectively with Z: -Q-CQ-, - CQ-Q-, -CH2-Q-; -Q-CH2-, -CQ-Q-CH2, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH2-, -N = N-, S (O) n -, -CH2-S (O) n-, -CQ-, -S (O) n -CH2-, -C (R8) = NO-, -C (R8) = NO-CH2-, -N (R9) ) -, -CQ-N (R9) -, -NÍR CQ-, -Q-CQ-N (R9) -, -C (R8) = NN = CH-, -N (RVCQ-Q-, -CQ- NÍR ^ -CQ-Q-, -N (RYCQ-Q-CH2-, -QC (R8) = NO-CH2-, -N (R9) -C (R8) = NO-CH2-, -O-CH2- C (R8) = NO-CH2-, -N = NC (R8) = NO-CH2-, -C (= NO-R10) -C (R8) = NO-CH2-, -C (= NOR, 0) -C (R) -ON = CH-, -C (= NO-RI0) -C (R8) = NN = CH-, -C (= NO-R10) -C (R8) -ON = C (CH3) -, -T-Ar1- or T-Ar'-Q-, where n means the numbers 0, 1 or 2, Q means oxygen or sulfur, R8 means hydrogen, cyano, methyl, ethyl or cyclopropyl and R9 means hydrogen, methyl , ethyl or cyclopropyl, R10 means hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or means benzyl optionally substituted by fluorine, by chlorine, by bromine, by cyano , by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by non-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, for trifluoromethoxy, for difluorochloromethoxy or for trifluoroethoxy, T means a single bond, means oxygen, sulfur, -CH2-O-, -CH2-S- or means substituted alkanediyl, if appropriate, Ar1 means phenylene or pyridinediyl substituted respectively given one to three times, in the same or in different forms, means pyrimidindiyl, pyridazindiyl, pyrazindiyl, 1,2,3-triazindiyl,
1,2,4-triazindiyl or 1,3,5-triazindiyl respectively monosubstituted, if any, or means 1,2,4-thiadiazoldiyl, 1,3,4-thiadiazoldiyl,
1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy , n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylisulfinyl, ethylsulfinyl, methylisulfonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyl-sulphonyl or trifluoromethyl-sulfonyl and L1 , L2, L3 and L4 are the same or different and respectively independently of each other, hydrogen, fluorine, chlorine, bromine, methyl or ethyl, W means hydrogen, fluorine, cyano or thiocyanate, and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-l-yl, 2- (l-methyl) -propyl, 2-methyl-2-buten-l-yl, propargyl, tetrahydropyranyl, tetrazol t-butyl substituted or means phenyl, 1,2,4-thiadiazolyl, 1,3,4- thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, tetrahydrobenzofuranyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5- triazinyl substituted, if appropriate, one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: amino, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, formyl, n- or i- propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfomyl, ethylsulphinyl, methylsulfonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, means methylenedioxy, ethylenedioxy, respectively doubly linked, each optionally substituted by one four times, in the same or different ways by fluorine, by chlorine, by methyl, by trifluoromethyl or by ethyl, or means a grouping
A1-, N O '
wherein A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, or cyclobutyl and A2 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methyl thiomethyl, ethylthiomethyl , methyl thioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl. Independently of the definitions given above, G also means particularly preferably: oxygen or means one of the following groupings, in which the left side is linked respectively with Z: -Q-CH2-, -C (R8) = NO- CH2-, -N = C (R8) -Q-CH2-, -CH (R8, -ON = CH -, - C (R8) = NN = CH-, -C (= NO-R10) -C (R8) ) = NO-CH2-, -C (= NO-R10) -C (R8) -ON = CH-, -C (= NOR, 0) -C (R8) -NN = CH- or T-Ar'- Q- wherein R8, R9, R10, T, Ar1 and Q have the abovementioned meanings preferably, particularly preferably L1, L2, L3 and L4 independently of each other, hydrogen.
Particularly preferably, Q means oxygen. Particularly preferably, W means hydrogen. A very particularly preferred group of compounds according to the invention are those compounds of formula (I) in which A denotes hydrogen, ethoxycarbonyl, methyl or ethyl, cyclopropyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio,
2,2,2-trifluoroethylthio, 1,1-difluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyln- or i-propylthiocarbonyl, phenylthio substituted, optionally one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i -, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R) R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 >; means methyl, ethyl, n- or i-propyl, n-, i-, - s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t- butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1, as well as with a nitrogen atom, with which they are bound, mean pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 3 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or phenyl optionally substituted one to three times, fluorine, chlorine, bromine, cyano, nitro, methyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy by, for trifluoromethoxy, by diflúorclorometoxi for trifluoroethoxy , methoxycarbonyl or ethoxycarbonyl, R * "means methylthio, ethylthio, n- or i-propylthio, n- i-, s- or t-butylthio, metiisulfonilo, etiisulfonilo, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio , dichlorofl ormetiltio, trichloromethylthio or 2,2,2-triflúoretiltio, or together with R3 and with the nitrogen atom to which they are attached represent pyrrolidino, piperidino or morpholino are optionally substituted by methyl or ethyl, R5 is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i, -s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same grouping as is bonded to the sulfur atom, or, when a is methyl, also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, i-butoxycarbonyl, metoxicarbonilcarbonilo, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, metiisulfonilo, etiisulfonilo, phenylsulfonyl or tolylsulfonyl, G represents oxygen or especially -O-CH2-, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cy ano or thiocyanate, and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-l-yl, 2-methyl-2-buten-l -yl, propargyl, tetrahydropyranyl or means phenyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, metiisulfinilo, ethylsulfinyl, metiisulfonilo or etiisulfonilo, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoro-ethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyl-sulphonyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, methylenedioxy or ethylenedioxy respectively doubly linked, each optionally substituted one to four times, in the same or in the same way different by flú or, by chlorine, by methyl, by trifluoromethyl or by ethyl or a grouping
A 'AV. ^ N O
where A 1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and A2 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl. A particularly preferred group of compounds according to the invention are those compounds of the formula (I), in which A denotes hydrogen, ethyl or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i- propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio,
2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted, optionally one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), -CN, -CH2-O-R5, -POIOR ^ R7, -PS (OR6 R7, where R1 signifies methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1, as well as with the nitrogen atom, to which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 3 means methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl or, phenyl optionally substituted one to three times by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t- butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio, n- or -propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, or 2,2,2-trifluoroethylthio, or together with R3 , as well as with the nitrogen atom, to which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i, -s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group that is already bonded to the sulfur atom, or, when A means methyl, also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl.
G means -C (R8) = NO-CH2, R8 means cyclopropyl or especially methyl, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate and Z means methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl, propargyl, or means pyridyl, pyrimidyl, or, especially substituted phenyl respectively, optionally from one to three times, in the same or in different ways, the possible substituents being preferably chosen as follows: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i -, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylisulfinyl, ethylsulfyl, methylsulfonyl or ethylsulfonyl, Trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, metoximinometilo, etoximinometilo, metoximinoetilo, etoximinoetilo, methylenedioxy or ethylenedioxy respectively doubly attached each substituted optionally one to four times, in the same or different ways by fluorine, by chlorine, by methyl, by trifluoromethyl or by ethyl. Another especially preferred group of compounds according to the invention are those compounds of the formula (I), in which A means hydrogen, ethyl or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio , n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted in case given from one to three times, by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy , by ethoxy, by non-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N ( R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies methyl, ethyl, n- or i-pro pilo, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R1, as well as with the nitrogen atom, to which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R3 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl or phenyl optionally substituted one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-tri Fluoroethylthio, or together with R 3, as well as with the nitrogen atom, with which they are bound, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group that is already bonded to the sulfur atom, or when A means methyl, R also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl, G means -T-Ar'-O, Ar1 means 1,2 4-thiadiazoldiyl, 1, 3,4-thiadiazoldiyl, 1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl or means pyridindiyl, pyrimidindiyl or 1,3, 5-triazindiyl, each optionally substituted one or two times, in the same or different manner by fluorine, by chlorine, by cyano, by methyl, by cyclopropyl, by methoxy, by methylthio, by trifluoromethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, T means a single bond, means oxygen, sulfur, -CH2-O-, CH2-S-, methylene, ethylene or propylene and L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-l-yl,
2- (1-methyl) -propyl, 2-methyl-2-buten-1-yl, propargyl or means pyridyl, pyrimidyl, thienyl, tetrahydrobenzofuranyl or especially phenyl, each optionally substituted one to three times, in the same or in different forms by amino, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, formyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for trifluoromethyl, for substituted t-butyl tetrazole, for methoxy, for ethoxy, for n- or i-propoxy, for difluoromethoxy, for difluorochloromethoxy, for trifluoroethoxy, for trifluoromethoxy, for methoximinomethyl, for ethoximinoethyl, for methoximinoethyl, by ethoxymethyl or methylenedioxy or ethylenedioxy respectively double-bonded, respectively optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl. In addition, another particularly preferred group of compounds according to the invention are those compounds of the formula (I), in which A means hydrogen or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio,
2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted, optionally, one to three times fluorine, chlorine, bromine, cyano, methyl or ethyl , by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), - CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1, as well as with the nitrogen atom, to which they are linked, means pyrrolidino, piperidino, morpholino, optionally substituted by methyl or ethyl, R 3 means methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl or fe nyl, optionally substituted one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i- propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulphonyl, n- or i-propylsulphonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R3, as with the nitrogen atom, with which they are bound, it means pyrrolidino, piperidino, or morpholino, optionally substituted by methyl or by ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino, or diethylamino, Y means the same group that is bonded to the sulfur atom, or, when A means methyl, R means also acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, or tolylsulfonyl, G stands for -C (= NO-R10) -C (R8) = NO-CH2- where R8 means methyl or cyclopropyl and R10 means hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or means benzyl optionally substituted by fluorine, by chlorine, by bromine, by cyano , by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butylby methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy or by trifluoroethoxy, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, cyano or thiocyanate and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl or means pyridyl, pyrimidyl or especially phenyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl , difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluo rmethylsulfmyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoxymethyl, ethoxymethyl, methylenedioxy, ethylenedioxy, respectively double-bonded, respectively substituted one to four times, in the same or different ways by fluorine, by chlorine, by methyl, by trifluoromethyl or by ethyl, or substituted tetra-t-butyl. Particularly preferred are the compounds of the formula (I), in which
A means methyl. Especially preferred are compounds of the formula (I), in which G is oxygen, -O-CH 2, -C (CH 3) = N-O-CH 2 - or pyrimidinyloxy optionally substituted by fluorine. Particularly preferred are compounds of the formula (I), in which Z means unsubstituted or mono- or disubstituted phenyl. Particularly preferred are the compounds of the formula (I) in which R denotes the abovementioned substituents, bonded through sulfur, such as especially alkyl-, haloalkyl-, phenyl-, optionally substituted, alkoxycarbonyl- or dialkylamino-thio . Particularly preferred are compounds of the formula (I), in which W denotes hydrogen.
Especially preferred are compounds of the formula (I), in which L 1, L 2, L 3 and L 4 are hydrogen. The definitions of the residues indicated above in a general manner or indicated in the preferred ranges are valid both for the final products of the formula (I) and also, correspondingly, for the starting products or for the intermediate products necessary respectively for obtaining. The definitions of the residues can be combined arbitrarily with each other, that is to say even between the indicated ranges of the preferred compounds. The amides, which are necessary as starting materials for carrying out the process according to the invention for the preparation of the methoxyiminophenylacetic acid amides of the formula (I), are generally defined by the formula (II). In this formula (II) A, G, L1, L2, L3, L4, W and Z preferably have or especially those meanings which have already been mentioned above, preferably or particularly preferably for A, G, L1, L2 , L3, L4, W and Z in relation to the description of the compounds according to the invention of the formula (I). The amides of the formula (I) are known and can be prepared according to known methods (see, for example, EP-A-398 692, EP-A-528 681, WO 98/21 189). The electrophilic reagents, which are also necessary as starting materials for carrying out the process according to the invention for the preparation of the methoximinophenylacetic acid amides of the formula (I), are defined by the formula (I). X means a dissociable group, such as, for example, halogen, preferably chlorine. When R means alkylcarbonyl, carboxylic acid anhydrides will also be considered as compounds of the formula (III), that is to say that R means -CO-R ', where R' signifies alkyl, preferably methyl or ethyl. When R means alkylaminocarbonyl, the corresponding isocyanates will also be considered as reactants of the formula (III). All the reagents of the formula (III) are chemical products for known synthesis and the person skilled in the art knows perfectly well which reagent is considered in each particular case. Suitable diluents for carrying out the process according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane, or trichloroethane, ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, or anisole; ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile, amides, such as N, N-dimethylformamide, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide; esters such as methyl acetate or ethyl acetate; sulfoxides such as dimethisulfoxide, sulfones, such as sulfolane; or alcohols, just as you do. -butanol. The process according to the invention is carried out, if appropriate, in the presence of a suitable acid acceptor. As such, all usual inorganic or organic bases are suitable. These preferably include hydrides, hydroxides, amides, alcoholates, carbonates or bicarbonates of alkaline earth metals or alkali metals, such as, for example, sodium hydride, potassium hydride, sodium amide, potassium tert-butylate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate, as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N -methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). The reaction temperatures in carrying out the process according to the invention can vary within wide limits. In general, work is carried out at temperatures of -100 ° C to 80 ° C, preferably at temperatures of -80 ° C to 50 ° C. To carry out the process according to the invention for the preparation of the compounds of the formula (I), generally 1 to 3 moles, preferably 1 to 2 moles, are used per mole of the amide of the formula (I). of the electrophilic reagent of the formula (III). The conduct of the reaction, the preparation and the isolation of the products of the reaction are carried out according to customary methods (see also the preparation examples). The products according to the invention have a powerful microbicidal effect and can be used in practice to combat undesired micro-organisms, such as fungi and bacteria, in the protection of plants and in the protection of materials. Fungicidal agents are used in the protection of plants for the fight against plasmodioforomycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes, deuteromycetes. Bactericidal agents are used in the protection of plants to combat pseudomonadaceos, rhizobiaceous, enterobacteriaceous, corynebacteriaceous and streptomycete. Some pathogens of fungal and bacterial diseases, which fall within the general definitions listed above, may be mentioned by way of example, but without any limiting character: types of xanthomonas, such as, for example, Xanthomonas campestris pv. oryzae; pseudomonas types, such as, for example, Pseudomonas syringae pv. lachrymans; types of erwinia, such as for example Erwinia amylovora; types of pitium, such as for example Pythium ultimun; phytophthora types, such as for example Phytophthora infestans; pseudoperonospora types, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; types of plasmopara, such as for example Plasmopara viticola; types of bremia, such as for example Bremia lactucae; types of peronospora, such as, for example, Peronospora pisi or P. brassicae; types of erisife, such as for example Erysiphe graminis; types of sphaerotheca, such as for example Sphaerotheca fuliginea; types of podosfaera, such as for example Podosphaera leucotricha; types of venturia, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. gramínea; (form of conidia, Drechslera, synonym: Helminthosporium); types of cocliobolus, such as for example Cochliobolus sativus (conideas form, Drechslera, synonym: Henminthosporium); types of uromices, such as, for example, Uromyces appendiculatus; types of pucinia, such as for example Puccinia recondita; Types of sclerotinia, such as for example Sclerotinia sclerotiorum; types of tilletia, such as for example Tilletia caries; types of ustylago, such as, for example, Ustilago nuda or Ustilago avenae; types of pelicularia, such as for example Pellicularia sasakii; blasting types, such as, for example, Pyricularia oryzae; fusarium types, such as, for example, Fusarium culmorum; Botrytis types, such as, for example, Botrytis cinerea; Septoria types, such as, for example, Septoria nodorum; types of leptosphaeria, such as for example Leptosphaeria nodorum; types of cercospora, such as for example Cercospora canescens; alternating types, such as, for example, Alternaria brassicae; types of pseudocercosporela, such as, for example, Pseudocercosporella herpotrichoides. The good compatibility with plants and active products at the concentrations necessary for the fight against plant diseases allows a treatment of the aerial parts of the plants, of seedlings and seeds and of the soil. In this case, the active compounds according to the invention will be used with particularly good success in the control of cereal diseases, such as, for example, against Erysiphe types, Puccinia or Fusarium types, diseases in culture crops. vines, fruit trees and vegetables, such as, for example, against types of Venturia, Sphaerotheca Podosphaera and Plasmopara, or rice diseases, such as, for example, Pyricularia types. In addition, the compounds according to the invention can be used to increase harvesting of the crops. They are also of low toxicity and have good compatibility with plants. The active products will be transformed, depending on their respective physical and / or chemical properties, into the usual formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, microencapsulated in polymeric materials and in coating compositions. for seeds, as well as ultra-low volume cold and hot fog (ULV) formulations. These formulations are prepared in known manner, for example by mixing the active compounds with extenders, that is, with liquid solvents, liquefied gases under pressure and / or solid excipients, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foam generating means. When water is used as an extender, organic solvents can be used, for example, as auxiliary solvents. Preferred liquid solvents are: aromatic hydrocarbons, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol, or glycol, as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide as well as water; liquefied gaseous excipients or excipients are those liquids which are gaseous at normal temperature and pressure, for example propellant gases for aerosols, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide; as solid excipients, the ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and the synthetic molten minerals, such as highly dispersed silicic acid, aluminum oxide and silicates; as solid excipients for granulates, broken and fractionated natural minerals, such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granulates of organic material, such as sawdust, walnut shells, can be used of coconut, corn ears and tobacco stems; suitable emulsifiers and / or foamers are, for example, non-ionogenic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated esters of fatty alcohols, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulphates, Aryl sulfonates as well as albumin hydrolysates; Dispersants include sulfite lignin bleach and methylcellulose. Adhesives, such as carboxymethylcellulose and natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as phospholipids, such as cephalin and lecithin and synthetic phospholipids can be used in the formulations. . Other additives can be mineral or vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, Prussian blue titanium oxide and organic dyes, such as metallic alizarin, azo and phthalocyanine dyes as well as trace nutrients, such as iron, manganese salts, boron, copper, cobalt, molybdenum and cmc. The formulations contain, in general, between 0.1 and 95% by weight, preferably between 0.5 and 90% of active product. The active products will be transformed, depending on their respective physical and / or chemical properties, into the usual formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, microencapsulated in polymeric materials and in coating compositions. for seeds, as well as ultra-low volume cold and hot fog (ULV) formulations. The active compounds according to the invention can be used as such or in their formulations even in admixture with cone fungicides, bactericides, acaricides, nematicides or insecticides to expand the spectrum of activity or to overcome resistance developments. In many cases synergistic effects are obtained in this way, that is to say that the activity of the mixture is greater than the activities of the individual components. The following compounds are suitable as the mixing components: Fungicides: Aldimorph, Ampropylfos, Ampropylfos-potassium, Andoprim, Anilazin, Azaconazole, Azoxystrobin, Benalaxyl, Bonodanil, Benomyl, Benzamacril, Benzamacryl-isobutyl, Bialaphos, Binapacryl, Biphenyl, Bitertanol, Blasticidin -S, Bromuconazole, Bupirimat, Buthiobat, Calcium Polysulfide, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Chinomethionat (Quinomethionat), Chlobenthiazon, Chlorfenazole, Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Clozylacon, Cufraneb, Cymoxanil, Cyproconazole, Cyprodinil, Cyprofuram, Debacarb, Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazole, Dimethirimol, Dimethomo h, Diniconazole, Diniconazole-M, Dinocap, Diphenylamin, Dipyrithione, Ditalimphos, Dithianon, Dodemorph, Dodine, Drazoxolon, Ediphenphos, Epoxiconazole , Etaconazole, Ethyrimol, Etriadiazole, Famoxadon, Fenapanil, Fenarimol, Fenbuconazole, Fenfuram, Fenitrop an, Fenpiclonil, Fenpropidin, Fenpropimofh, Fentinacetat, Fentinhidroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazole, Flufrimidol, Flusilazol, Flusulfamid, Flutolanil, Flutriafol, Folpet, Fosetyl-aluminum, Fosetyl-sodium, Fthalid, Fuberidazole, Furalaxyl, Furametpyr, Furcarbonil, Furconazol, Furconazol-cis, Fumercyclox, Guazatin, hexachlorobenzene, Hexaconazole, Hymexazole, Imazalil, Imibenconazole, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazole, Iprobenfos (PPI), Iprodione, Irumamycin, Isoprothiolan, Isovaledione, Kasugamycin, Kresoxim -methyl, copper preparation, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, copper oxine and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepromil, Metalaxyl, Metconazole, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin, Nickel dimethyldithiocarbamate, Nitr othal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin, Paclobutrazol, Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin,
Piperalin, Polyoxin, Polyoxorim, Probenazole, Prochloraz, Procymidon,
Propamocarb, Propanosine-sodium, Propiconazole, Propineb, Pyrazophos, Pyrifenox,
Pyrimethanil, pyroquilon, Pyroxyf r, quinconazole, Quintozen (PCNB), sulfur and sulfur preparations, tebuconazole, tecloftalam, Tecnazen, Tetcyclacis, tetraconazole, thiabendazole,
Thicyofen, Thifluzamide, Tthiophanate-methyl, Thiram, Thioxymid, Tolclofos-methyl,
Tolylfluanid, triadimefon, triadimenol, triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemofh, Triflumizole, Triforin, triticonazole, uniconazole, Validamycin A, vinclozolin, viniconazole, zarilamid, zineb, Zira and Dagger G, OK-8705, OK-8801, to - (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1 H- 1,2,4-triazole-1-ethanol, a- (2,4-dichlorophenyl) -β-fluoro-b-propyl- lH-L, 2,4-triazole-1-ethanol, a- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1, 2,4-triazole-1-ethanol, - (5- methyl-l, 3-dioxan-5-yl) -β - [[4- (trifluoromethyl) -phenyl] -methylene] -lH-l, 2,4-triazole-l-ethanol, (5RS, 6RS) -6 -hydroxy-2,2,7,7-tetramethyl-5- (lH-1, 2,4-triazol-1-yl) -3-octanone, (E) -a- (methoxyimino) -N-methyl-2 -phenoxy-phenylacetamide,. { 2-methyl-1 - [[[1- (4-methylphenyl) -ethyl] -amino] -carbonyl] -propyl} 1-isopropyl carbamate, 1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanon-O- (phenylmethyl) -oxime, 1- (2 -methyl-1-naphthalenyl) - lH-pyrrole-2, 5-dione, 1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, 1 - [(diy odomethyl) - sulfonyl] -4-methyl-benzene, l - [[2- (2,4-dichlorophenyl) -l, 3-dioxolan-2-yl] -methyl] -lH-imidazole, l - [[2- (4- chlorophenyl) -3-phenyloxyranyl] -methyl] -lH-1, 2,4-triazole, 1 - [1 - [2- [(2,4-dichlorophenyl) -methoxy] -phenyl] -ethenyl] -1H- imidazole, 1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6'-dibromo-2-methyl-4'-tr iflúormetoxi-4'-methyl- -triflúor 1, 3-thiazole -5-carboxanilide, 2,2-dichloro-N- [1- (4-chlorophenyl) -ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide, 2,6-dichloro-5- (methylthio) -4 pyrimidinyl thiocyanate, 2, 6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide, 2, 6-dichloro-N- [[4- (iflúormetil tr) -phenyl] -methyl] -benzamide, 2- (2 , 3,3-triiodo-2-prope-nyl) -2H-tetrazole, 2 - [(1-methylethyl) -sulfonyl] -5- (trichloromethyl) -1,3,4-t iadiazole, 2 - [[6-deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] -amino] -4-methoxy-1H-pyrrolo [2, 3-d ] pyrimidine-5-car-bonitrile, 2-aminobutane, 2-bromo-2- (bromomethyl) -pentandinitrile, 2-chloro-N- (2,3-dihydro-l, 1,3-trimethyl-lH-inden- 4-yl) -3-pyridinecarboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide, 2-phenylphenol (OPP), 3,4-dichloro- 1 - [4- ( difluoromethoxy) -phenyl] -1H-pyrrole-2, -di-one, 3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide, 3- ( l, 1-dimethylpropyl) -l-oxo-lH-inden-2-carbonitrile, 3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine, 4-chloro-2-cyan-N , N-dimethyl-5- (4-methylphenyl) -lH-imidazole-1-sulfonamide, 4-methyl-tetrazolo [1, 5-a] quinazolin-5 (4H) -one, 8- (1, 1-dimethylethyl) ) -N-ethyl-N-propyl-l, 4-dioxaspiro [4,5] decan-2-methanamine, 8-hidroxiquinolinsulfato, 2 - [(phenylamino) carbonyl] hydrazide 9H-xanthene acid-9-carboxylic acid , bis- (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophenecarboxylate, cis- 1 - (4-chlorophenyl) -2- (1 H- 1,2,4-triazol-1-yl) -cycloheptanol, cis-4- [3- [4- (1, 1-dimethylpropyl) -phenyl-2-hydrochloride. methylpropyl] -2,6-dimethyl-morpholine, ethyl - [(4-chlorophenyl) azo] -cianoacetato, potassium bicarbonate, sodium salt Methantetrathiol-methyl- 1 - (2, 3-dihydro-2, 2- dimethyl-1 H-inden-1-yl) -1 H-imidazole-5-carboxylate, methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate, methyl-N- ( chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate, N- (2,3-dichloro-4-hydroxyphenyl) -l-methyl-cyclohexanecarboxamide, N- (2,6-dimethylphenyl) -2-methoxy -N- (tetrahydro-2-oxo-3-furanyl) -acetamide, N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) -acetamide, N- ( 2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) -l, 4,5,6-tetrahydro-2-pyrimidinamine, N- (4-hexylphenyl) -l 4,5,6-tetrahydro-2-pyrimidinamine, N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide, N- (6-methoxy) -3-pyridinyl) -cyclopropanecarboxamide, N- [2 , 2,2-trichloro-l - [(chloroacetyl) -amino] -ethyl] -benzamide, N- [3-chloro-4,5-bis- (2-propynyloxy) -phenyl] -N'-methoxy-methanimidoamide , N-formyl-N-hydroxy-DL-alanine, sodium salt O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] -ethyl-phosphoramidothioate, O-methyl-S-phenyl-phenylpropylphosphoramidothioate, S-methyl-1 , 2,3-benzothiadiazole-7-carbothioate, spiro [2 H] -1-benzopyran-2, 1 '(3' H) -isobenzoft? -an-3'-one. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin,
Octhilinon, furanocarboxylic acid, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, copper sulfate and other copper preparations. Insecticides / Acaricides / Nematicides: Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin, Bacillus popilliae, Bacillus sphaericus , Bacillus subtilis, Bacillus thuringiensis, Baculoviren, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomethrin, Biopermethrin, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiophos, Butocarboxim, Butylpiridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyphos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlofyrifos, Chlofyrifos M, Covaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin , Cyhexatin, Cypermethrin, Cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dymethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiophencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenoxuron, Flutenzine, Fluvalinate, Fonophos, Fosmethilan , Fosthiazate, Fubfenprox, Furathiocarb, Granulosevirus, Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazophos, Isofenphos, Isoxathion, Ivemectin, Nuclear polyhedrovirus, Lamda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Metaldehyd, Methamidophos, Metarhizium anisopliae , Metharhizium flavoviride, Methidathion, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos, Naled, Nitenpyram, Nithiazine, Novaluron, Omethoat, Oxamyl, Oxydemethon M, Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiophos, Prothoat, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion, Pyrimidifen, Pyriproxifen, Quinalphos, Ribavirin, Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos, Tau Fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Termivinphos, Terbufos, Tetrachlorvinphos,
Thetacypermethrin, Thiametohoxam, Thiapronil, Thiatriphos, Thiocyclan hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralomethrin,
Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon,
Triflumuron, Trimethacarb, Vamidothion, Vaniliprole, Verticillium lecanii, Yl 5302, Zeta-cypermethrin, Zolaprofos, (lR-cis) - [5- (phenylmethyl) -3-furanyl-methyl-3 - [(dihydro-2-oxo-3 (2H) -furanylidene) -methyl] -2,2-dimethylcyclopropanecarboxylate, (3-phenoxyphenyl) -methyl-2,2,3,3-tetramethylcyclopropanecarboxylate, 1 - [(2-chloro-5-thiazolyl) methyl] tetrahydro- 3,5-dimethyl-N-nitro-l, 3,5-lthiazin-2 (lH) -imine,
2- (2-Chloro-6-fluorophenyl) -4- [4- (1, 1-dimethylethyl) phenyl] -4,5-dihydro-oxazole, 2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione , 2-chloro-N- [[[4- (1-phenylethoxy) -phenyl] -amino] -carbonyl] -benzamide, 2-chloro-N - [[[4- (2,2-dichloro-1, -difluoretoxy) -phenyl] -amino] -carbonyl] -benzamide,
3 - . 3-methylphenyl-propylcarbamate, 4- [4- (4-ethoxyphenyl) -4-methylpentyl] -l-fluoro-2-phenoxy-benzene, 4-chloro-2- (1, 1-dimethylethyl) -5 - [[ 2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -3 (2H) -pyridazinone, 4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(iodo-3-pyridinyl ) methoxy] -3 (2H) -pyridazinone, 4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone, from Bacillus thuringiensis strain EG-2348, [2-benzoyl- l- (l, l-dimethylethyl) -hydrazide of benzoic acid, butanoate of 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-l-oxaspiro [4.5] dec-3-en-4 -yl, [3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cianamide, dihydro-2- (nitromethylene) -2H-l, 3-thiazine-3 (4H) -carboxaldehyde, ethyl - [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxo] ethyl] -carbamate, N- (3,4,4-trifluor-1-oxo-3) -butenyl) -glycine, N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-lH-pyra2? -l-carboxamide, N - [(2-chloro -5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine, N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazindicarbotioamide, N-methyl-N" - 2-propenyl-l, 2-hydrazindicarbothioamide, O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioate, It is also possible to mix with other known active ingredients, such as herbicides or even with fertilizers and regulators d growth. The active compounds can be used as such in the form of their formulations or in the forms of application prepared from the above, such as ready-to-use solutions, suspensions, injectable powders, pastes, soluble powders, dusts and granules. The use is carried out in a conventional manner, for example by watering, spraying, sprinkling, spreading, dusting, foaming, brush application, etc. It is also possible to apply the active products also according to the ultra-low volume process or to inject the active product preparation or the active product itself into the soil. The seeds of the plants can also be treated.
When the active compounds according to the invention are used as fungicides, the amounts applied can vary within wide limits, depending on the type of application. When treating parts of plants, the applied amounts of active compound are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of the treatment of the seeds, the quantities of active product are generally between 0.001 and 50 g per kilogram of seeds, preferably between 0.01 and 10 g per kilogram of seeds. When the soil is treated, the application amounts are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha. Examples of obtaining. Example 1.
They are added to a suspension of 0.17 g (4.2 mmoles) of sodium hydride (60% in mineral oil) in 15 ml of tetrahydrofuran, at 0 to 5 ° C, 1.1 g (3.5 mmoles) of 2-methoximino-2 [2- (methylphenoxy) -methylphenyl] -N-methyl-acetamide and the mixture is stirred for 30 minutes additionally. Under additional cooling, 0.483 g (3.9 mmol) of methoxycarbonylsulfenyl chloride are then added dropwise at -70 ° C. The reaction mixture is then stirred overnight at room temperature, the inorganic material is separated by filtration and the solvent is distilled off in a vacuum. The residue is chromatographed with cyclohexane / ethyl acetate (3: 1) on silica gel. 1.24 g (88% of theory) of 2-methoximino-2 [2- (methylphenoxy) -methylphenyl] -N-methyl-N-methoxycarbonylthioacetamide are obtained as a colorless oil. HPLC: logP = 4.25. Example 2
3.15 g (0.00663 mol) of 2- are dissolved. { 2- [6- (2-bromophenoxy) -5-fluoro-pyrimidin-4-yloxy] phenyl} -2-methoxyimino-N-methyl-acetamide in 25 ml of pyridine and refrigerate at 0 ° C. 1.12 g (0.0066 mol) of dichlorofluoromethanesulfenyl chloride are added dropwise and the mixture is subsequently stirred for 8 hours at 5 ° C. The reaction mixture is poured into 200 ml of 2N hydrochloric acid cooled with ice and extracted with diethyl ether. The organic phase is dried over sodium sulfate and the solvent is distilled off in vacuo. The residue is chromatographed with n-hexane: acetone = 4: 1 on silica gel. 0.3 g (6.07% of theory, HPLC content: 81.6%) of 2- are obtained. { 2- [6- (2-bromo-phenoxy) -5-fluoro-pyrimidin-4-yloxy] phenyl} -N- (dichlorofluoro-methylsulfanyl) -2-methoxyimino-N-methylacetamide. logP = 5.10 LC / MS: M = 614, 612, 611,609, 607, 598, 577, 520, 489, 478, 477, 475,459, 457, 388, 366. Spectrum? -NMR (DMSOd6 / TMS): d = 3.35 (3H); 3.74 (3H); 7.29-7.34 (1H); 7.40-7.62 (6H); 7.78-7.81 (1H); 8.17 (1H) ppm. In a manner analogous to that of Examples 1 and 2, and also according to the general description of the process obtained according to the invention for the preparation of the compounds of the formula (I), the compounds of the formula (Ia) were also obtained according to the invention, following, indicated in table I.
Table 1: Example Z G R A logP P.f. (° C)
3 2-ChloroRY -S-CCbF -CH3 -H 5.05 phenyl 4 2-Tolyl -O-CH2- -CN -H -H 3.34 196
2-Tolyl -O-CH 2 -S-CChF -CH 3 -H 5,35 6 2-Tolyl -O-CH 2 -S-CC 13 -CHs -H 5,56 65
7 2-Tolyl -O-CH 2 -4-Fluorophenylthio -CH 3 -H 5,11
8 2-Tolyl -O-CH 2 -CH 3 -H 4,24 9 2-Tolyl -O-CH 2 -SN (C 4 H 9) 2 -CH 3 -H 6,83 10 2-Tolyl -O-CH 2 -CN -CH 3 -H 3.67 11 2-Tolyl -O-CH 2 4-Methoxyphenylthio -CH 3 -H 4,98 12 2-Tolyl -O-CH 2 -COOC 2 H 5 -CH 3 -H 4, 46 Table 1:
Table 1:
Table 1:
Table 1:
Table 1: Example Z G R A W logP P.f. (° C)
61 2-Tolyl -O-CH2- -S-CF3 cyclo-H 5,17 propyl 62 2-Tolyl -O-CH 2 -S-CF 3 -C 2 H 5 -H 5,3
63 -. 63 -O-CH2- -S-CChF -CH3 -H 5.69
64 -O-CH 2 -S-CF 3 -CH 3 -H 5,27 65 3-Phenylphenyl -O-CH 2 -S-CChF -CHs -H 5,77 66 3-Phenylphenyl -O-CH 2 -S-CF 3 -CH 3 -H 5,36 67 2,5-Dimethyl- -O-CH 2 -S-CCI 2 F -CHs -H 5,68 phenyl 68 2,5-Dimethyl- -O-CH 2 -S-CF 3 -CH 3 - H 5.25 phenyl 69 2,5-Difluoro- -O-CH 2 -S-CCkF -CH 3 -H 4,86 phenyl 70 2,5-Difluoro- -O-CH 2 -S-CF 3 -CH 3 -H 4 , 48 phenyl Table 1: Ex. RW logP Pf (° C)
71 3-Trifluoro- -S-CH3 -CHs -H 4.73 methylphenyl
72 3-Trifluor-S-Phenyl-CH 3 -H 5,48 methylphenyl
73 3-Trifluoro- -S-C2H5 -CHs -H 5,02 methylphenyl
74 3-Trifluoro-3-trifluoride- -CH 3 -H 5,84 methylphenylphenylphenyl
75 3-Trifluoro- -S-CF3 -CH3 -H 5.36 methylphenyl
6 3-Trifluoro- -CO- -CHs -H 5,22 methylphenyl N (CH 3) -S-CF 3 Table 1: Ex. R W logP P.f. (° C)
HS
77 3-Chloro- - -S-CCbF -CH3 -H 5.79 phenyl
H3 N- ° 78 3-Chloro- -S-CF3 -CH3 -H 5.39 phenyl
79 3,4-dime- -S-CChF -CH3 -H 4.7 linden
80 3,4-Dime- -S-CF3 -CH3 -H 4,36 toxiphenyl
9H3
81 3-Chlorophenyl? -S- -CH3 -H 4.71 COOCH3
2 3,4-Dimeto- -S- -CH 3 -H 3,7 xyphenyl COOCH 3 Table 1: Example Z G R A W logP P.f. (° C)
83 3-Fluoride-S-CChF-CH3 -H 5.36 phenyl
84 3-Fluorine-S-CF3-CH3 -H 4.97 phenyl
3-Chloro-2-S-CChF-CH3 -H 5.59 128-130 methylphenyl
87 2-Chloro-3-S-CChF-CH 3 -H 4,72 formyl phenyl Table 1: Ex. Z G R A W log P P.f. (° C)
88 Phenyl S-CChF-CHs -H 4.76
89 2-Tolyl-S-CChF-CH3 -H 5.05
90 2,4-Dime-S-CChF-CHs -H 5,41 tilphenyl
91 2,3-Diclo-S-CChF-CHs -H 5,46 Rophenyl
92 2,3-Dime- -S-CChF -CH3 -H 5,34 tilphenyl
93 2-Trifluoro- -S-CChF -CH3 -H 5,2 methoxyphenyl Table 1: Ex. Z R W logP P.f. (° C)
94 2-Difluoro- -S-CChF-CHs -H 4,7 methoxyphenyl-
95 2-Ethylthio- -S-CChF -CH3 -H 5.36 methylphenyl
CChF
7 2,6-Dimethyl- S-CChF -CH 3 -H 5,4 phenyl
8 2-Chlorophenyl -S-CChF-CHs -F 4.84 Table 1: Example Z G R A W logP P.f. (° C)
trifluoride-toxiphenyl
100 3-Methoxy-S-CChF-CHs -H 5,81 iminomethyl-phenyl
101 3-Bromo-phenyl
102 2,4-Dichloro- -S-CChF -CH3 -H 5.6 phenyl
103 3,5-Dichloro- -S-CChF -CH 3 -H 5,71 phenyl Table 1: Example Z G R A logP P.f. (° C)
104 4-Bromo- • S-CChF-CHs -H 5,19 phenyl
105 2-Fluorophenyl -S-CChF -CH3 -H 4.73
106 3-Trifluoro- -S-CChF -CH3 -H 5,11 methylphenyl
107 4-Cyanophenyl -S-CChF -CHs -H 4.34
108 4-Methoxyphenyl-S-CChF-CH3 -H 4.63
? P? ox 109 2-Ethylphenyl? -S-CChF -CH 3 -H 5,25 Table 1:
, 25 Table 1: Example Z G R A W logP P.f. (° C)
115 3,4-Diclo-S-CChF-CHs -H 5,58 Rophenyl
116 2,4-Difluoro- -S-CChF -CHs -H 4,85 phenyl
117 3-Chlorophenyl -S-CChF -CH3 -H 5.14
118 3-Fluorophenyl -S-CChF-CHs -H 4.76
119 2-Cyanophenyl -S-CChF -CH3 -H 4.28
120 4-Tolyl -S-CChF -CH3 -H 5.02 Table 1: Ex. Z G R A W logP P.f. (° C)
121 2,5-Di- S-CChF-CHs -H 5,34 Methylphenyl
122 2-Allyl-nyl
123 2- (i-pro- -S-CChF -CH3 -H 5.56 pil) phenyl
124 2-Isopro- -S-CChF -CH3 -H 5.88 pil-5-methylphenyl
125 3-Chloro-6-S-CChF-CH 3 -H 5,46 methylphenyl Table 1: Ex. R W logP P.f. (° C)
126 2-Chloro-3 -S-CChF -CH3 -H 5,42 trifluoromethylphenyl
127 4-Yodofeni -S-CChF -CHs -H 5.35
128 3-Tolyl -CChF -CHs -H 4.98
129 2-methoxy- -S-CChF -CH3 -H 4,57 phenyl
130 3-Methoxy-S-CChF-CH 3 -H 4,68 phenyl
131 4-Ethylphenyl -S-CChF-CH3 -H 5.38 Table 1: Ex. R W logP P.f. (° C)
132 3- (t-bu- -S-CChF-CHs -H 5.84 useful) -phenyl
133 4-Trifluor-S-CChF-CHs -H 5,3 methoxyphenyl
134 2- (l-methyl) - S-CChF-CHs -H 5.86 propylphenyl
136 4-Amino-2,3-S-CChF-CHs -H 4,68 dichlorophenyl Table 1: Ex. R W logP P.f. (° C)
137 3-EÜ1-5- -S-CChF -CHs -H 5.76 Methylphenyl
138 2-Methyl-4- -S-CChF-CHs -H 5,65 trifluoromethyl-toxiphenyl
139 4-Trifluor-S-CChF-CHs -H 5,6-methyl-thio-phenyl
140 2-Methoxy-S-CChF-CHs -H 5,03 iminomethylphenyl Table 1: Example Z G R A W logP P.f. (° C)
141 3-Chloro-S-CChF-CHs -H 5.29 128.0 2-methyl-phenyl 142 2-Tetrahi- -O- -S-CChF -CHs -F dropir añilo oil
143 Phenyl-S-CChF-CHs -H 5.48
144 2,6-Difluoro-phenyl -CO-O- -S-CChF -CHs -H 4,41 79
145 -. 145 -CHs -S-CChF -CHs -H 5.45 146 -CHs -O- -S-CChF -CHs -H 3.69
*) The determination of the logP values was carried out according to EEC Directive 79/831 Annex V. A8 by HPLC gradient method, acetonitrile / 0.1% aqueous phosphoric acid).
Application examples: Example A Plasmopara (vine) / protector assay. Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and solvent and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active product at the indicated application amounts. After drying of the spray-applied coating, the plants are inoculated with an aqueous suspension of Plasmopara spores and then remain for 1 day in an incubation chamber at 20 ° C and 100% relative humidity of the air. The plants are then placed for 5 days in the greenhouse at 21 ° C and a relative humidity of approximately 90%. The planas are then moistened and placed in an incubation cabin for one day. The evaluation is carried out 6 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the untreated controls, while a degree of activity of 100% means that no attack is observed. In this test the compounds indicated in the preparation examples (1), (3), (5), (6), (7), (8), (9), (11), (13), (20) are shown ), (21), (22), (23), (24), (25), (26), (32), (40), (44), (46), (52), (54), (55), (56), (57), (61), (63), (64), (66), (67), (68), (69), (70), (71), (72) ), (73), (75), (86), (88), (91), (92), (93), (97), (100), (101), (102), (105), (106), (109), (117), (128), (141) and (143), with an application amount of 100 g / ha, an activity level of 90% or greater than this value.
Example B Test with Podosphaera (apple tree) / protector Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and solvent and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After drying the spray-applied coating, the plants are inoculated with an aqueous suspension of the anthracnose of the apple tree Podosphaera leucotricha. The plants are then placed in the greenhouse at approximately 23 ° C and with a relative humidity of approximately 70%. The evaluation is carried out 10 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the untreated controls, while a degree of activity of 100% means that no attack is observed. In this test the compounds indicated in the preparation examples (1), (5), (6), (7), (10), (11), (13), (20), (21), (22) are shown ), (23), (26), (32), (40),
(46), (52), (54), (56), (57), (61), (64), (66), (67), (68), (69), (70), (72) ), (75), (86), (88), (91), (92), (100), (101), (141) and (143), with an application quantity of 100 g / ha, a activity level of 90% or greater than this value. EXAMPLE C Assay with Sphaerotheca (cucumber) / protector. Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether.
To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and solvent and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After drying the spray applied coating, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in the greenhouse at approximately 23 ° C and a relative humidity of about 70% in the greenhouse. The evaluation is carried out 10 days after the inoculation. In this case
0% means a degree of activity that corresponds to that of untreated controls, while a degree of activity of 100% means that no attack is observed. In this test, the compounds indicated in the preparation examples (1), (3), (5), (6), (7), (8), (9), (11), (12), (13) are shown ), (20), (21), (22), (23), (24), (25), (26), (32), (40), (44), (45), (46), (52), (54), (55), (56), (57), (61), (63), (64), (66), (67), (68), (69), (71) ), (72), (73), (75), (86), (88), (91), (92), (93), (97), (100), (101), (102), (105), (106), (109), (117), (128), (141) and (143), with an application amount of 100 g / ha, an activity level of 90% or greater than this value. Example D Test with Venturia (apple tree) / protector. Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After drying of the spray-formed coating, the plants are inoculated with an aqueous suspension of conidia of the anthracnose pathogen Venturia inaequalis and then remain for 1 day at 20 ° C and 100% relative humidity in an incubation chamber. The plants are then placed in the greenhouse at approximately 21 ° C and with a relative humidity of approximately 90%. The evaluation is carried out 12 days after the inoculation. In this case
0% means a degree of activity that corresponds to that of untreated controls, while a degree of activity of 100% means that no attack is observed. In this test the compounds indicated in the preparation examples (1), (3), (5), (6), (7), (8), (9), (10), (11), (12) are shown ), (13), (14), (15), (20), (21), (22), (23), (24), (25), (26), (32), (40), (44), (52), (54), (55), (56), (57), (63), (64), (66), (71), (72), (73), (75 ), (86), (88), (91), (92), (93), (97), (100), (101), (102), (105), (106), (109), (117), (128), (141) and (143), with an application amount of 10 g / ha, an activity level of 90% or greater than this value. Example E: Test with Pyricularia (rice) / protector Solvent: 25 parts by weight of N, N-dimethylacetamide Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether To obtain a suitable preparation of active compound, 1 part by weight of the active product with the indicated amount of solvent and the concentrate is diluted with water and with the indicated amount of emulsifier to the desired concentration. To test the protective activity, young rice plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the spray applied coating, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants are then placed in a greenhouse at a temperature of 25 ° C and a relative humidity of 100%. The evaluation is carried out 4 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed. In this test the products according to the invention, indicated in examples (1) and (5), with an application amount of 125 g / ha, an activity level of 90% or above this value, are shown. Example F Test with Erysiphe (barley) / protector. Solvent: 25 parts by weight of N, N-dimethylacetamide. Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amounts. After drying of the spray-applied coating the plants are sprinkled with spores of Erysiphe graminis f.sp. hordei The plants are placed in a greenhouse at a temperature of about 20 ° C and a relative humidity of about 80% to promote the development of powdery mildew pustules. The evaluation occurs 7 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed. In this test it shows the product according to the invention, indicated in example (5), with an application amount of 250 g / ha, an activity degree of 90% or above this value. Example G Test with Erysiphe (wheat) / protector. Solvent: 25 parts by weight of N, N-dimethylacetamide. Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active ingredients, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and diluted with water to the desired concentration. To check the protective activity, young plants are sprayed with the preparation of active product in the indicated application quantities. After drying the spray-applied coating, the plants are sprinkled with spores of Erysiphe graminis f. sp. tritici. The plants are placed in a greenhouse at a temperature of about 20 ° C and a relative humidity of about 80% to promote the development of powdery mildew pustules. The evaluation occurs 7 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed.
In this test it shows the product according to the invention, indicated in example (5), with an application amount of 250 g / ha, an activity degree of 90% or above this value. Example H Pucinia (wheat) / protector test Solvent: 25 parts by weight of N, N-dimethylacetamide Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are inoculated with the preparation of active compound in the indicated application amounts. After drying of the spray-applied coating, the plants are sprayed with a conidial suspension of recondite Puccinia. The plants remain for 48 hours at 20 ° C and with a relative humidity of 100% in an incubation cabinet. The plants are then placed in a greenhouse at a temperature of about 20 ° C and with a relative humidity of about 80%, to favor the development of rust pustules. The evaluation is carried out 10 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed. In this test it shows the product according to the invention, indicated in example (5), with an application amount of 250 g / ha, an activity degree of 90% or above this value.
EXAMPLE I Assay with Fusarium nivale (var. Nivale) (wheat) / protector. Solvent: 25 parts by weight of N, N-dimethylacetamide. Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After drying the spray-applied coating, the plants are sprinkled with a suspension of conids of Fusarium nivale (var. Nivale). The plants are placed in a greenhouse, under incubation caps transparent to light, at a temperature of approximately 15 ° C and a relative humidity of approximately 100%. The evaluation is carried out 4 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the untreated controls, while a degree of activity of 100% means that no attack is observed. In this test, the compounds indicated in the preparation examples (5), (67), (68), (100), (101), (102), (103), (104), (105), (106) are shown ), (109),
(114), (115), (116), (117), (118), (119), (120), (121), (122), (123), (124), (125),
(126), (130), (134), (138) and (139), with an application amount of 250 g / ha, an activity level of 90% or greater than this value.
E emplo K Test with Erysiphe (barley) / healing. Solvent: 25 parts by weight of N, N-dimethylacetamide. Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the curative activity, young plants are sprayed with spores of Erysiphe graminis f.sp. hordei After 48 hours from the inoculation, the plants are sprayed with the preparation of active compound at the indicated application rates. The plants are placed in a greenhouse at a temperature of approximately 20 ° C and a relative humidity of approximately 80%, to favor the development of the powdery mildew pustules. The evaluation is carried out 7 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the untreated controls, while a degree of activity of 100% means that no attack is observed. In this test, the compounds indicated in the preparation examples (5), (67), (68), (100), (101), (102), (103), (106), (107), (108) are shown ), (109),
(110), (113), (114), (115), (116), (117), (119), (123), (124), and (128), with an application amount of 250 g / has, an activity level of 90% or greater than this value. It is noted that in relation to this date, the best method known to the applicant, to carry out the aforementioned invention is that which is clear from the present description of the invention.
Claims (2)
1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy , n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, metiisulfonilo or etiisulfonilo, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl and L1 , L, L3 and L4 are the same or different and respectively independently of each other, hydrogen, fluorine, chlorine, bromine, methyl or ethyl, W means hydrogen, fluorine, cyano or thiocyanate, and means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-l-yl, 2- (l-methyl) -propyl, 2-methyl-2-buten-l-yl, propargyl , tetrahydropyranyl, tetrazol t-butyl substituted or means phenyl, 1,2,4-thiadiazolyl, 1,3,4- thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, tetrahydrobenzofuranyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5- triazinyl substituted, if appropriate, one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: amino, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, formyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, non-propylthio, methylisulfinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, means methylenedioxy, ethylenedioxy, respectively doubly linked, respectively substituted one to four times or sometimes, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl, or means a grouping YEAR where A means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, or cyclobutyl and A2 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl. 4. Compounds of the formula (I) according to claim 1, characterized by park A means hydrogen, ethoxycarbonyl, methyl or ethyl, cyclopropyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio , n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2, 2-trifluoroethylthio, 1,1-difluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted one to three times, fluorine, chlorine, bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl , by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R) R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies methyl, ethyl, n- or i-propyl, n-, i-, - s- or t-butyl, R2 means methyl, ethyl, n- or i -propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1, as well as with a nitrogen atom, with which they are bound, mean pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R3 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or phenyl optionally substituted one to three times, fluorine, chlorine, bromine, cyano, nitro, methyl, n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy , by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i-propylthio, n- i-, s- or t-butylthio, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio , trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R3 as well as with the nitrogen atom, to which they are bound, mean pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i, -s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same grouping as is bonded to the sulfur atom, or, when A means methyl, also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, i-butoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl, G stands for oxygen or especially -O-CH2-, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate, and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl, propargyl, tetrahydropyranyl or phenyl means respectively substituted one to three times, in the same or in the same way different, the possible substituents being chosen preferably from the following enumeration: fluorine, chlorine or, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- propylthio, methylsulfinyl, ethylsulfinyl, metiisulfonilo or etiisulfonilo, trifluoromethyl, diflúormetoxi.triflúormetoxi, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, methylenedioxy or ethylenedioxy respectively doubly attached respectively substituted optionally a four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl or a group A ^ N wherein A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and A2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl , ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl. 5. Compounds of the formula (I) according to claim 1, characterized by perc. A means hydrogen, ethyl or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted, optionally, one to three times, fluorine, chlorine, bromine, cyano, methyl , by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methoxycarbonyl or ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbon nyl, or together with R 1, as well as with the nitrogen atom, with which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 3 signifying methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, phenyl optionally substituted one to three times by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl R 4 means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, or , 2,2-trifluoroethylthio, or together with R 3, as well as with the nitrogen atom, with which they are bound, means pyrrolidino, p iperidino or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i- propyl, n-, i, -s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group which is already bonded to the sulfur atom, or, when A means methyl, R also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl , dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl. G means -C (R8) = NO-CH2, R8 means cyclopropyl or especially methyl, L1 ', TV2, TV3 and V mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate and Z means methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl, propargyl, or means pyridyl, pyrimidyl, or , especially phenyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen as the following number: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylisulfinyl, ethylsulfyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy , difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyl-sulphonyl or trifluoromethyl-sulfonyl, methoxycarbonyl, ethoxic respectively double-bonded arbonyl, methoximinomethyl, ethoxyminomethyl, methoxymethyl, ethoxymethyl, methylenedioxy or ethylenedioxy, each optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl. 6. Compounds of the formula (I) according to claim 1, face? eriza ± e pceque A means hydrogen, ethyl or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio , trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), -CN, -CH2-O-R5, -POÍOR ^ R7, -PS (OR6) R7, where R1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, methoxy arbonyl or ethoxycarbonyl, or together with R 1, as well as with the nitrogen atom, with which they are bound, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 3 means methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl or phenyl, optionally substituted one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i- propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R 3, as well as with the nitrogen atom, with which they are linked, Examples of pyrrolidino, piperidino or morpholino substituted, if appropriate, by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group that is already bonded to the sulfur atom, or, when A means methyl, R also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2- bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl, G stands for -T-Ar'-O, Ar 1 means 1,2,4-thiadiazoldiyl, 1,3,4-thiadiazoldiyl, 1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl or means pyridindiyl, pyrimidindiyl or 1,3,5-triazindiyl respectively substituted one or two times, in the same or in different ways entities by fluorine, by chlorine, by cyano, by methyl, by cyclopropyl, by methoxy, by methylthio, by trifluoromethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, T means a single bond, means oxygen, sulfur, -CH2-O- , CH2-S-, methylene, ethylene or propylene and L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate and Z means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, 2-buten-l-yl,
2- (1-methyl) -propyl, 2-methyl-2-buten-1-yl, propargyl or means pyridyl, pyrimidyl, thienyl, tetrahydrobenzofuranyl or especially phenyl, each optionally substituted one to three times, in the same or in different forms by amino, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, formyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for trifluoromethyl, for substituted t-butyl tetrazole, for methoxy, for ethoxy, for n- or i-propoxy, for difluoromethoxy, for difluorochloromethoxy, for trifluoroethoxy, for trifluoromethoxy, for methoximinomethyl, for ethoximinoethyl, for methoximinoethyl, by ethoxymethyl or methylenedioxy or ethylenedioxy respectively double-bonded, respectively optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl. 7. Compounds of the formula (I), according to claim 1, characterized in that A is hydrogen or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted, if appropriate, three times fluorine, chlorine, bromine, cyano, methyl or ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), - CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means met ilo, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R1, as well as with the nitrogen atom, with which they are bound, means pyrrolidino, piperidino, morpholino, optionally substituted by methyl or ethyl, R 3 is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or optionally substituted phenyl one to three times, by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- i-propoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methoxycarbonyl or ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R3, as well as the nitrogen atom, to which they are linked, means pyrrolidino, piperidino, or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino, or diethylamino, Y means the same group that is bonded to the sulfur atom, or, when A means methyl, also means acetyl , propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, or tolylsulfonyl, G stands for -C (= NO-R10) -C (R8) = NO-CH2- where R8 means methyl or cyclopropyl and R10 means hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or means benzyl optionally substituted by fl uo r, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i -propoxi, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy or by trifluoroethoxy, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, cyano or thiocyanate and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl or means pyridyl, pyrimidyl or especially phenyl substituted respectively in each case three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylisulfinyl, ethylsulfinyl, methylisulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio , trifluoromethyl-sulphonyl or trifluoromethyl-sulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoxymethyl, methoxymethyl, ethoxymethyl, methylenedioxy, ethylenedioxy, respectively double-bonded, respectively substituted in the case of one to four times, in the same or in different ways by fluorine, chlorine, methyl, trifluoromethyl or by ethyl, or substituted tetra-t-butyl. 8. Compounds according to claim 1, characterize pcxque G means oxygen or means one of the following groupings, in which the left side is linked respectively with Z: -Q-CH2-, -C (R8) = NO-CH2- , -CH (R8) -ON = CH-, -C (R8) = NN = CH-, -C (= NOR, 0) -C (R8) = NO-CH2-, -C (= NO-RI0) -C (R8) -ON = CH-, -C (= NO-R10) -C (R8) -NN = CH- or T-Ar'-Q- where R8, R9, R10, T, Ar1 and Q, have the meanings indicated in claim 1. 9. Compounds of the formula (I) according to claim 1, characterize perqu A means methyl. 10. Compounds of the formula (I) according to claim 1, characterized by perch G means oxygen, -O-CH2-, -C (CH2) = N-O-CH2- or pyrimidinyloxy, optionally substituted by fluorine. 11. Compounds of the formula (I) according to claim 1, cararterized park Z means unsubstituted or mono or disubstituted phenyl. 12.- Agents containing extender and / or support materials as well as, if appropriate, surfactant products, characterized in that they have a content in at least one compound as described in claim 1. 13.- Procedure for the control of pests , characterized in that compounds are allowed to act on the pests and / or on their environment as defined in claim 1 or agents as defined in claim 12. 14. Use of the compounds as defined in claims 1 to 11 or of the agents as defined in claim 12, for the control of pests. 15. Process for obtaining agents characterized in that compounds such as those defined in claims 1 to 11 are mixed with extenders and / or surfactants. 16. Process for obtaining compounds of the formula (I), as defined in claim 1, characterized in that amides of the formula (II) are reacted wherein A, G, L1, L2, L3, L4, W and Z have the meanings indicated in claim 1, with an electrophilic reagent of the formula (III), RX (III) in which R has the indicated meaning in claim 1, and X means a dissociable group, optionally in the presence of a diluent and, if appropriate, in the presence of a base.
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