RU98121313A - SUBSTITUTED AMINOMETHYLPHENYL SULPHONYLMOLAINS, THEIR RECEIVING AND USING AS HERBICIDES AND PLANT GROWTH REGULATORS - Google Patents
SUBSTITUTED AMINOMETHYLPHENYL SULPHONYLMOLAINS, THEIR RECEIVING AND USING AS HERBICIDES AND PLANT GROWTH REGULATORSInfo
- Publication number
- RU98121313A RU98121313A RU98121313/04A RU98121313A RU98121313A RU 98121313 A RU98121313 A RU 98121313A RU 98121313/04 A RU98121313/04 A RU 98121313/04A RU 98121313 A RU98121313 A RU 98121313A RU 98121313 A RU98121313 A RU 98121313A
- Authority
- RU
- Russia
- Prior art keywords
- carbon atoms
- alkyl
- alkoxy
- residues
- group
- Prior art date
Links
- -1 AMINOMETHYLPHENYL Chemical class 0.000 title claims 6
- 239000004009 herbicide Substances 0.000 title claims 2
- 239000005648 plant growth regulator Substances 0.000 title claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 209
- 125000000217 alkyl group Chemical group 0.000 claims 80
- 125000003545 alkoxy group Chemical group 0.000 claims 42
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000004414 alkyl thio group Chemical group 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000011780 sodium chloride Substances 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 239000001301 oxygen Substances 0.000 claims 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 241000196324 Embryophyta Species 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 230000003993 interaction Effects 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 4
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 3
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims 3
- 150000001350 alkyl halides Chemical class 0.000 claims 3
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 3
- 125000005139 alkynylsulfonyl group Chemical group 0.000 claims 3
- 125000004429 atoms Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 2
- 230000002363 herbicidal Effects 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 2
- 230000001105 regulatory Effects 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N benzenesulfonimidic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001276 controlling effect Effects 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- 150000002829 nitrogen Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N oxygen atom Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 229960001663 sulfanilamide Drugs 0.000 claims 1
- 125000004434 sulfur atoms Chemical group 0.000 claims 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims 1
Claims (9)
где R1 означает NR8R9, углеводородный остаток, который незамещен или замещен; R8 и R9, независимо друг от друга, означают водород, алкил с 1-4 атомами углерода, алкоксил с 1-4 атомами углерода, алкилкарбонил с 1-4 атомами углерода в алкильной части или алкилсульфонил с 1-4 атомами углерода; n означает нуль, 1 или 2, за исключением значений нуль или один, когда R1 означает NR8R9; R2 и R3, независимо друг от друга, означают водород или алкил с 1-4 атомами углерода; R4 означает водород, гидроксил, формил, остаток формулы R, R-O-, R-CO- или R-SO2-, причем R означает углеводородный остаток, который незамещен или замещен; R5 означает ацильный остаток, или NR4R5 вместе означают гетероциклический остаток, который незамещен или замещен; W означает атом кислорода или серы; R6 означает водород, алкил с 1-4 атомами углерода, алкоксил с 1-4 атомами углерода, алкилгиогруппу с 1-4 атомами углерода, алкилкарбонил с 1-4 атомами углерода в алкильной части, алкоксикарбонил с 1-4 атомами углерода в алкоксильной части, причем каждый из указанных последними остатков незамещен или замещен одним или несколькими атомами галогена, или галоген, нитрогруппу, цианогруппу или моно- или дизамещенную аминогруппу; R7 означает водород или алкил с 1-4 атомами углерода; А означает остаток формулы:
один из остатков Х и Y означает водород, алкил с 1-3 атомами углерода или алкоксил с 1-3 атомами углерода, причем оба указанных последними остатка незамещены или однократно или многократно замещены галогеном или однократно замещены алкоксилом с 1-3 атомами углерода, и другой из остатков Х и Y означает водород, галоген, алкил с 1-3 атомами углерода, алкоксил с 1-3 атомами углерода или алкилгиогруппу с 1-3 атомами углерода, причем три указанных последними, алкилсодержащих остатка незамещены или однократно или многократно замещены галогеном или однократно или двукратно замещены алкоксилом с 1-3 атомами углерода или алкилтиогруппой с 1-3 атомами углерода, или остаток формулы NRaRb, где Ra и Rb независимо друг от друга, означают водород, алкил с 1-3 атомами углерода или алкенил с 2-3 атомами углерода, или циклоалкил с 3-6 атомами углерода, алкенил с 2-4 атомами углерода, алкинил с 2-4 атомами углерода, алкенилоксигруппу с 3-4 атомами углерода или алкинилоксигруппу с 3-4 атомами углерода; Z означает метин или азот; X1 означает метил, метоксигруппу, этоксигруппу или дифторметоксигруппу; Y1 означает оксогруппу или метилен; Х2 означает метил, этил или 2,2,2-трифторэтил; Y2 означает метоксигруппу, этоксигруппу, тиометил, тиоэтил, метил или этил; Х3 означает метил или метоксигруппу; Y3 означает водород или метил; Х4 означает метил, метоксигруппу, этоксигруппу, метоксиметил или хлор; Y4 означает метил, метоксигруппу, этоксигруппу или хлор; и Y5 означает метил, этил, метоксигруппу или хлор.1. The compounds of formula I or their salts
where R 1 means NR 8 R 9 , a hydrocarbon residue that is unsubstituted or substituted; R 8 and R 9 , independently of one another, denote hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylcarbonyl with 1-4 carbon atoms in the alkyl part or alkylsulfonyl with 1-4 carbon atoms; n is zero, 1 or 2, except for the values zero or one, when R 1 is NR 8 R 9 ; R 2 and R 3 , independently of one another, denote hydrogen or alkyl with 1-4 carbon atoms; R 4 is hydrogen, hydroxyl, formyl, a radical of the formula R, RO—, R — CO— or R — SO 2 -, wherein R is a hydrocarbon residue which is unsubstituted or substituted; R 5 is an acyl residue, or NR 4 R 5 together is a heterocyclic residue which is unsubstituted or substituted; W denotes an oxygen or sulfur atom; R 6 means hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylgroup with 1-4 carbon atoms, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part , each of these last residues unsubstituted or substituted by one or more halogen atoms, or halogen, nitro, cyano or mono - or disubstituted amino group; R 7 means hydrogen or alkyl with 1-4 carbon atoms; A means the residue of the formula:
one of the X and Y residues is hydrogen, alkyl with 1–3 carbon atoms or alkoxy with 1–3 carbon atoms, both of which are indicated by the latter are unsubstituted or are substituted once or several times by halogen or once replaced by alkoxy with 1–3 carbon atoms, and the other of X and Y are hydrogen, halogen, alkyl with 1–3 carbon atoms, alkoxy with 1–3 carbon atoms, or an alkyl halogen group with 1–3 carbon atoms, the latter three of which are alkyl containing residues are unsubstituted or substituted once or several times with halogen or one atno or disubstituted by alkoxy with 1-3 carbon atoms or alkylthio of 1-3 carbon atoms, or a radical of the formula NR a R b, where R a and R b independently represent hydrogen, alkyl having 1-3 carbon atoms or alkenyl with 2-3 carbon atoms, or cycloalkyl with 3-6 carbon atoms, alkenyl with 2-4 carbon atoms, alkynyl with 2-4 carbon atoms, alkenyloxy group with 3-4 carbon atoms or alkynyloxy group with 3-4 carbon atoms; Z is methin or nitrogen; X 1 is methyl, methoxy, ethoxy, or difluoromethoxy; Y 1 means oxoprop or methylene; X 2 is methyl, ethyl or 2,2,2-trifluoroethyl; Y 2 is methoxy, ethoxy, thiomethyl, thioethyl, methyl or ethyl; X 3 is methyl or methoxy; Y 3 is hydrogen or methyl; X 4 is methyl, methoxy, ethoxy, methoxymethyl or chloro; Y 4 is methyl, methoxy, ethoxy or chloro; and Y 5 is methyl, ethyl, methoxy or chloro.
T означает кислород или серу; R10 означает алкил с 1-4 атомами углерода, алкенил с 3-4 атомами углерода или алкинил с 3-4 атомами углерода, причем каждый из трех указанных последними остатков незамещен или замещен одним или несколькими остатками, выбираемыми из группы, состоящей из галогена, алкоксила с 1-4 атомами углерода, алкилтиогруппы с 1-4 атомами углерода, алкилкарбонила с 1-4 атомами углерода в алкильной части и алкоксикарбонила с 1-4 атомами углерода в алкоксильной части; R11 и R12, независимо друг от друга, означают водород, алкил с 1-4 атомами углерода, алкенил с 3-4 атомами углерода или алкинил с 3-4 атомами углерода, причем каждый из трех указанных последними остатков незамещен или замещен одним или несколькими остатками, выбираемыми из группы, состоящей из галогена, алкоксила с 1-4 атомами углерода, алкилтиогруппы с 1-4 атомами углерода, алкилкарбонила с 1-4 атомами углерода в алкильной части и алкоксикарбонила с 1-4 атомами углерода в алкоксильной части; остатки R13 вместе с атомом азота означают пяти- или шестичленный гетероцикл, который может содержать дальнейшие гетероатомы, выбираемые из группы, состоящей из азота, кислорода и серы в возможных степенях окисления, и незамещен или замещен алкилом с 1-4 атомами углерода или оксогруппой или конденсирован с бензольным циклом; или R4 и R5 вместе означают цепь формулы (-CH2)m1B1- или В1-(СH2)m2В2, причем отдельные метиленовые группы могут быть заменены атомами кислорода и причем цепь незамещена или замещена одним или несколькими алкильными остатками с 1-3 атомами углерода или галогеном и m1 означает 3, 4 или 5, соответственно, m2 означает 2, 3 или 4, а также В1 и В2, независимо друг от друга, означают сульфонил или карбонил, R6 означает водород, алкил с 1-4 атомами углерода, алкоксил с 1-4 атомами углерода, алкилгиогруппу с 1-4 атомами углерода, алкилкарбонил с 1-4 атомами углерода в алкильной части или алкоксикарбонил с 1-4 атомами углерода в алкоксильной части, причем каждый из указанных последними пяти остатков незамещен или в алкильной части замещен одним или несколькими атомами галогена; или галоген, нитрогруппу, цианогруппу или моно- или диалкиламиногруппу с 1-4 атомами углерода в каждой алкильной части; R7 означает водород или алкил с 1-4 атомами углерода.2. Compounds or their salts under item 1, characterized in that R 1 means NR 8 R 9 , alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, alkynyl with 2-6 carbon atoms, cycloalkyl with 3 -6 carbon atoms, cycloalkenyl with 3-6 carbon atoms or phenyl, each of these last six residues unsubstituted or substituted by one or more residues selected from the group consisting of halogen, cyano, alkoxyl with 1-4 carbon atoms, halogenoalkoxy with 1-4 carbon atoms, alkoxyalkoxy with 1-4 carbon atoms in each alkoxy part, alkylthio groups with 1-4 carbon atoms, alkylsulfinyl with 1-4 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, formyl, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, alkylcarbonyloxy group with 1-4 carbon atoms in the alkyl part and, in the case of cyclic residues, also alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms and alkoxyalkyl with 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl parts; R 8 means alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms or cycloalkenyl with 3-6 carbon atoms; R 9 is hydrogen or alkyl with 1-4 carbon atoms; n is nude, 1 or 2, except for the values zero or one, when R 1 is NR 8 R 9 ; R 2 and R 3, independently of one another, are hydrogen or alkyl with 1-4 carbon atoms; W means oxygen or sulfur; R 4 means hydrogen, hydroxyl, formyl, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, alkynyl with 2-6 carbon atoms, alkoxy with 1-6 carbon atoms, alkenyloxy group with 2-5 carbon atoms, alkynyloxy group with 2-5 carbon atoms, alkylcarbonyl with 1-6 carbon atoms in the alkyl part, alkylsulfonyl with 1-6 carbon atoms, alkenylcarbonyl with 2-6 carbon atoms in the alkenyl part, alkenylsulfonyl with 2-6 carbon atoms, alkynylcarbonyl with 2-6 carbon atoms in the alkynyl moiety, alkynyl sulfonyl with 2-6 carbon atoms, cycloalkyl with 3-6 a carbon volumes, cycloalkenyl with 3-6 carbon atoms, cycloalkylcarbonyl with 3-6 carbon atoms in the cycloalkyl part, cycloalkylsulfonyl with 3-6 carbon atoms, cycloalkenylcarbonyl with 3-6 carbon atoms in the cycloalkenyl part or cycloalkenylsulfonyl with 3-6 carbon atoms, each of these last eighteen residues is unsubstituted or substituted by one or more residues selected from the group consisting of halogen, alkoxy with 1-4 carbon atoms, alkylthio groups with 1-4 carbon atoms, alkylsulfinyl with 1-4 carbon atoms genus, alkylsulfonyl with 1-4 carbon atoms, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, alkylcarbonyloxy group with 1-4 carbon atoms in the alkyl part and cyano group and, in the case of cyclic residues also alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms; or phenylcarbonyl or phenylsulfonyl, and in both of these last residues the phenyl ring is unsubstituted or substituted by one or more residues selected from the group consisting of halogen, cyano, nitro, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms and halogenoalkane with 1-4 carbon atoms; R 5 means formyl, alkylcarbonyl with 1-6 carbon atoms in the alkyl part, alkenylcarbonyl with 2-6 carbon atoms in the alkenyl part, alkynylcarbonyl with 2-6 carbon atoms in the alkynyl part, alkylsulfonyl with 1-6 carbon atoms, alkenylsulfonyl with 2- 6 carbon atoms, alkynylsulfonyl with 2-6 carbon atoms, cycloalkylcarbonyl with 3-6 carbon atoms in the cycloalkyl part, cycloalkenylcarbonyl with 3-6 carbon atoms in the cycloalkenyl part, cycloalkylsulfonyl with 3-6 carbon atoms or cycloalkenylsulfonyl with 3-6 carbon atoms, and ka one of the ten last mentioned residues is unsubstituted or substituted by one or several residues selected from the group consisting of halogen, alkoxy with 1-4 carbon atoms, alkylthio groups with 1-4 carbon atoms, alkylsulfinyl with 1-4 carbon atoms, alkylsulfonyl with 1- 4 carbon atoms, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, alkylcarbonyloxy group with 1-4 carbon atoms in the alkyl part and cyano group and, in the case of cyclic residues, also alkyl with 1- 4 atoms mi carbon and halogenated with 1-4 carbon atoms; or phenylcarbonyl or phenylsulfonyl, each of the two last mentioned residues in the phenyl ring is unsubstituted or substituted by one or more residues selected from the group consisting of halogen, cyano, nigroup, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 atoms carbon, alkoxy with 1-4 carbon atoms and halogenoalkane with 1-4 carbon atoms, or mono - or dialkylaminosulfonyl with 1-4 carbon atoms in each alkyl part, which in the alkyl part unsubstituted or substituted by one or more residues, in taken from the group consisting of halogen, alkoxy with 1-4 carbon atoms, alkylthio groups with 1-4 carbon atoms, alkylsulfinyl with 1-4 carbon atoms, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, alkylcarbonyloxy group with 1-4 carbon atoms in the alkyl part, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part and cyano group; or a group of the formula COCOR ', where R' is hydrogen, hydroxyl, alkoxy with 1-4 carbon atoms or alkyl with 1-4 carbon atoms; or a group of the formula:
T means oxygen or sulfur; R 10 means alkyl with 1-4 carbon atoms, alkenyl with 3-4 carbon atoms or quinil with 3-4 carbon atoms, each of the three last mentioned residues unsubstituted or substituted by one or more residues selected from the group consisting of halogen, alkoxy with 1-4 carbon atoms, alkylthio groups with 1-4 carbon atoms, alkylcarbonyl with 1-4 carbon atoms in the alkyl part and alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part; R 11 and R 12 , independently of one another, mean hydrogen, alkyl with 1-4 carbon atoms, alkenyl with 3-4 carbon atoms or alkynyl with 3-4 carbon atoms, each of the three last residues being unsubstituted or substituted by one or several residues selected from the group consisting of halogen, alkoxy with 1-4 carbon atoms, alkylthio groups with 1-4 carbon atoms, alkylcarbonyl with 1-4 carbon atoms in the alkyl part and alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part; residues R 13 together with the nitrogen atom means a five or six membered heterocycle, which may contain further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur in possible oxidation states, and is unsubstituted or substituted by alkyl with 1-4 carbon atoms or an oxo group or condensed with a benzene cycle; or R 4 and R 5 together represent a chain of the formula (-CH 2 ) m1 B 1 - or B 1 - (CH 2 ) m2 B 2 , wherein individual methylene groups may be replaced by oxygen atoms and the chain is unsubstituted or substituted by one or more alkyl residues with 1-3 carbon atoms or halogen and m1 means 3, 4 or 5, respectively, m2 means 2, 3 or 4, as well as B 1 and B 2 , independently of each other, mean sulfonyl or carbonyl, R 6 means hydrogen , alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylgroup with 1-4 carbon atoms, alkylcarbonyl with 1-4 carbon atoms in an alkyl part or alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, each of the last five residues being unsubstituted or substituted in the alkyl part by one or more halogen atoms; or halogen, nitro, cyano or mono- or dialkylamino with 1-4 carbon atoms in each alkyl part; R 7 means hydrogen or alkyl with 1-4 carbon atoms.
T означает кислород или серу; R10 означает алкил с 1-4 атомами углерода, галогеналкил с 1-4 атомами углерода, алкенил с 3-4 атомами углерода или алкинил с 3-4 атомами углерода; R11 и R12, независимо друг от друга, означают водород или алкил с 1-4 атомами углерода; остатки R13 вместе означают алкиленовую цепь с четырьмя или пятью атомами углерода; или R4 и R5 вместе означают цепь формулы (-CH2)m1B1- или В1-(CH2)m2В2, причем отдельные метиленовые группы могут быть заменены атомами кислорода и причем цепь незамещена или замещена одним или несколькими алкильными остатками с 1-3 атомами углерода или галогеном и m1 означает 3, 4 или 5, соответственно, m2 означает 2, 3 или 4, а также B1 и В2, независимо друг от друга, означают сульфонил или карбонил; R6 означает водород, алкил с 1-4 атомами углерода, алкоксил с 1-4 атомами углерода или галоген; R7 означает водород или метил, А означает остаток формулы
один из остатков Х и Y означает алкил с 1-3 атомами углерода, галогеналкил с 1-3 атомами углерода, алкоксил с 1-3 атомами углерода или галогеналкоксил с 1-3 атомами углерода, и другой из остатков Х и Y означает алкил с 1-3 атомами углерода, галогеналкил с 1-3 атомами углерода, алкоксил с 1-3 атомами углерода, галогеналкоксил с 1-3 атомами углерода, галоген, алкиламиногруппу с 1-3 атомами углерода или диалкиламиногруппу с 1-3 атомами углерода в каждой алкильной части, Z означает метин или азот.3. Compounds or their salts under item 1 or 2, characterized in that R 1 means NR 8 R 9 , alkyl with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms or phenyl, each of these last three residues unsubstituted or substituted by one or more residues selected from the group consisting of halogen, cyano, alkoxy with 1-4 carbon atoms, halogenoalkoxy with 1-4 carbon atoms, alkylthio groups with 1-4 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, formyl, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, alkylcarbonyl hydroxy groups with 1-4 carbon atoms in the alkyl part and, in the case of cyclic residues, also alkyl with 1-4 carbon atoms, halogenalkyl with 1-4 carbon atoms and alkoxyalkyl with 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl part; or alkenyl with 2-4 carbon atoms or quinil with 2-4 carbon atoms; R 8 means alkyl with 1-4 carbon atoms; R 9 is hydrogen or alkyl with 1-4 carbon atoms; n is zero, 1 or 2, except for the values zero or one, when R 1 is NR 8 R 9 ; R 2 and R 3 , independently of one another, denote hydrogen or alkyl with 1-4 carbon atoms; W means oxygen or sulfur, R 4 means hydrogen, hydroxyl, formyl, alkyl with 1-4 carbon atoms, alkenyl with 2-4 carbon atoms, quinil with 2-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylcarbonyl with 1 -4 carbon atoms in the alkyl part, alkylsulfonyl with 1-4 carbon atoms, each of these last six residues unsubstituted or substituted by one or more residues selected from the group consisting of halogen and alkoxyl with 1-4 carbon atoms; or phenylcarbonyl or phenylsulfonyl, and in both of these last residues the phenyl ring is unsubstituted or substituted by one or more residues selected from the group consisting of halogen, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxyl with 1- 4 carbon atoms and halogenalkoxy with 1-4 carbon atoms; R 5 means formyl, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, alkenylcarbonyl with 2-4 carbon atoms in the alkenyl part, alkynylcarbonyl with 2-4 carbon atoms in the alkynyl part, alkylsulfonyl with 1-4 carbon atoms, alkenylsulfonyl with 2- 4 carbon atoms, alkynylsulfonyl with 2-4 carbon atoms, cycloalkylcarbonyl with 3-6 carbon atoms in the cycloalkyl part, and each of the seven last mentioned residues is unsubstituted or substituted by one or more residues selected from the group consisting of halogen, alkoxyl with 1- 4 at carbon, alkylthio groups with 1-4 carbon atoms, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, alkylcarbonyloxy groups with 1-4 carbon atoms in the alkyl part and cyano group and, in the case of cyclic residues, also alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms; or phenylcarbonyl or phenylsulfonyl, each of the two last mentioned residues in the phenyl ring is unsubstituted or substituted by one or several residues selected from the group consisting of halogen, cyano, nitro, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 atoms carbon, alkoxy with 1-4 carbon atoms and halogenoalkane with 1-4 carbon atoms; or mono- or dialkylaminosulfonyl with 1-4 carbon atoms in each alkyl part which is unsubstituted or substituted by one or more halogen atoms in the alkyl part, or a group of the formula COCOR ', where R' means hydrogen, hydroxyl, alkoxy with 1-4 carbon atoms or alkyl with 1-4 carbon atoms; or a group of the formula:
T means oxygen or sulfur; R 10 means alkyl with 1-4 carbon atoms, halogenated alkyl with 1-4 carbon atoms, alkenyl with 3-4 carbon atoms or quinil with 3-4 carbon atoms; R 11 and R 12 , independently of one another, are hydrogen or alkyl with 1-4 carbon atoms; residues R 13 together represent an alkylene chain with four or five carbon atoms; or R 4 and R 5 together represent a chain of the formula (-CH 2 ) m1 B 1 - or B 1 - (CH 2 ) m2 B 2 , wherein individual methylene groups can be replaced by oxygen atoms and the chain is unsubstituted or substituted by one or more alkyl residues with 1-3 carbon atoms or halogen and m1 means 3, 4 or 5, respectively, m2 means 2, 3 or 4, and B 1 and B 2 , independently of each other, mean sulfonyl or carbonyl; R 6 means hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms or halogen; R 7 means hydrogen or methyl, And means the residue of the formula
one of X and Y is alkyl with 1-3 carbon atoms, haloalkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms or halogenalkoxy with 1-3 carbon atoms, and the other of X and Y is alkyl with 1 -3 carbon atoms, haloalkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms, haloalkoxy with 1-3 carbon atoms, halogen, alkylamino group with 1-3 carbon atoms or dialkylamino group with 1-3 carbon atoms in each alkyl part , Z means methine or nitrogen.
вводят во взаимодействие с гетероциклическим карбаматом формулы III
R*-O-CO-NR7-A
где R* означает незамещенный или замещенный фенил или алкил с 1-4 атомами углерода; или б) арилсульфонилкарбамат формулы IV
где Аr означает арильный остаток, вводят во взаимодействие с аминогетероциклом формулы V
H-NR7-A
или в) сульфонилизоцианат формулы VI
вводят во взаимодействие с аминогетероциклом формулы Н-NR7-A (V); или г) по одностадийной реакции сначала аминогетероцикл формулы Н-NR7-А (V) в присутствии основания вводят во взаимодействие с фосгеном и образовавшееся промежуточное соединение вводят во взаимодействие с фенилсульфонамидом формулы II; или д) сульфонилхлорил формулы VII
вводят во взаимодействие с цианатом М-OCN, где М означает катион, и с аминогетероциклом формулы Н-NR7-А (V) в присутствии основания, или е) сульфонамид вышеприведенной формулы II вводят во взаимодействие с (тио)изоцианатом формулы V
W=C=N-A
в присутствии основания; причем в формулах II-VII и V' остатки, соответственно, символы R1 -R7, A, W и n имеют значение, как указанное для формулы I и причем в вариантах а) и в) - д) сначала получают соединения формулы I, где W означает кислород.5. The method of producing compounds of the formula I or their salts according to any one of paragraphs. 1-4, characterized in that a) compound of formula II
enter into interaction with heterocyclic carbamate of formula III
R * -O-CO-NR 7 -A
where R * means unsubstituted or substituted phenyl or alkyl with 1-4 carbon atoms; or b) arylsulfonylcarbamate of formula IV
where Ar means aryl residue, enter into interaction with aminoheterocycles of formula V
H-NR 7 -A
or c) a sulfonyl isocyanate of formula VI
enter into interaction with aminoheterocycles of the formula H-NR 7 -A (V); or d) in a one-step reaction, first an amino-heterocycle of formula H-NR 7 -A (V) in the presence of a base is reacted with phosgene and the resulting intermediate is reacted with phenylsulfonamide of formula II; or d) sulfonylchloride of formula VII
enter into interaction with cyanate M-OCN, where M is a cation, and with an amino heterocycle of the formula H-NR 7 -A (V) in the presence of a base, or e) the sulfonamide of the above formula II is brought into interaction with the (thio) isocyanate of the formula V
W = C = NA
in the presence of a base; moreover, in formulas II-VII and V ', the residues, respectively, the symbols R 1 -R 7 , A, W and n have the meaning as indicated for formula I and, moreover, in variants a) and c) - e) first, compounds of the formula I where W means oxygen.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19616445.1 | 1996-04-25 | ||
| DE19616445A DE19616445A1 (en) | 1996-04-25 | 1996-04-25 | Substituted aminomethylphenylsulfonylureas, process for their preparation and their use as herbicides and plant growth regulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98121313A true RU98121313A (en) | 2000-10-20 |
| RU2217425C2 RU2217425C2 (en) | 2003-11-27 |
Family
ID=7792361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98121313/04A RU2217425C2 (en) | 1996-04-25 | 1997-04-07 | Substituted aminomethylphenylsulfonylureas, method for their preparing, herbicide agent based on thereof, method for control of weed plants and intermediate compounds |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5925596A (en) |
| EP (1) | EP0900023B1 (en) |
| JP (1) | JP2000509378A (en) |
| CN (1) | CN1200609C (en) |
| AU (1) | AU710909B2 (en) |
| CA (1) | CA2252952C (en) |
| DE (2) | DE19616445A1 (en) |
| DK (1) | DK0900023T3 (en) |
| ES (1) | ES2187766T3 (en) |
| PL (1) | PL189802B1 (en) |
| RU (1) | RU2217425C2 (en) |
| WO (1) | WO1997040690A1 (en) |
| ZA (1) | ZA973549B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA974703B (en) * | 1996-05-30 | 1997-12-30 | Bayer Ag | Substituted sulfonylamino(thio)carbonyl compounds. |
| DE19702200A1 (en) * | 1997-01-23 | 1998-07-30 | Hoechst Schering Agrevo Gmbh | Phenylsulfonylureas, process for their preparation and their use as herbicides and plant growth regulators |
| DE10036184A1 (en) | 2000-07-24 | 2002-02-14 | Aventis Cropscience Gmbh | Substituted sulfonylaminomethylbenzoic acid (derivatives) and process for their preparation |
| CN103281905B (en) | 2010-12-21 | 2016-10-19 | 拜尔作物科学有限合伙公司 | The sand paper mutant of bacillus and for promoting plant growing, promoting plant health and control disease and the method for insect |
| EP2755485A1 (en) | 2011-09-12 | 2014-07-23 | Bayer Cropscience LP | Methods of enhancing health and/or promoting growth of a plant and/or of improving fruit ripening |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4678498A (en) * | 1985-06-12 | 1987-07-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| JPS6216457A (en) * | 1985-06-12 | 1987-01-24 | イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− | Herbicidal sulfonamides |
| US4927453A (en) * | 1986-10-17 | 1990-05-22 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| WO1989010921A1 (en) * | 1988-05-12 | 1989-11-16 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| DE4335297A1 (en) * | 1993-10-15 | 1995-04-20 | Hoechst Schering Agrevo Gmbh | Phenylsulfonylureas, process for their preparation and their use as herbicides and plant growth regulators |
-
1996
- 1996-04-25 DE DE19616445A patent/DE19616445A1/en not_active Withdrawn
-
1997
- 1997-04-07 ES ES97916445T patent/ES2187766T3/en not_active Expired - Lifetime
- 1997-04-07 CN CNB97194010XA patent/CN1200609C/en not_active Expired - Fee Related
- 1997-04-07 JP JP9538490A patent/JP2000509378A/en active Pending
- 1997-04-07 RU RU98121313/04A patent/RU2217425C2/en not_active IP Right Cessation
- 1997-04-07 CA CA002252952A patent/CA2252952C/en not_active Expired - Fee Related
- 1997-04-07 AU AU25091/97A patent/AU710909B2/en not_active Ceased
- 1997-04-07 DK DK97916445T patent/DK0900023T3/en active
- 1997-04-07 PL PL97329640A patent/PL189802B1/en not_active IP Right Cessation
- 1997-04-07 WO PCT/EP1997/001715 patent/WO1997040690A1/en active IP Right Grant
- 1997-04-07 EP EP97916445A patent/EP0900023B1/en not_active Expired - Lifetime
- 1997-04-07 DE DE59708829T patent/DE59708829D1/en not_active Expired - Fee Related
- 1997-04-24 ZA ZA9703549A patent/ZA973549B/en unknown
- 1997-04-24 US US08/842,490 patent/US5925596A/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU96109050A (en) | PHENYLSULFONILMOCHEVINY, METHOD OF THEIR PRODUCTION AND THEIR APPLICATION AS HERBICIDES AND PLANT GROWTH REGULATORS | |
| KR960704858A (en) | Phenylsulfonylurea, its preparation and its use as herbicide and plant growth regulator | |
| KR100236807B1 (en) | Aryl sulphonyl urea compounds, a method of preparing them, and their use as herbicides and growth regulators | |
| KR910007893A (en) | Sulfonylamino carbonyltriazolinone | |
| KR977002853A (en) | ACYLATED AMINOPHENYLSULPHONYLUREAS, PROCESS FOR THEIR PREPARATION AND THEIR USE AS HERBICIDES AND PLANTGROWTH REGULATORS | |
| RU96106900A (en) | Acylated Aminophenylsulfonylureas, Their Preparation and Use as Herbicides and Plant Growth Regulators | |
| KR960703402A (en) | ACYLATED AMINOPHENYL UREA COMPOUNDS, THEIR PREPARATION AND THEIR USE AS HERBICIDES AND PLANT-GROWTH REGULATORS | |
| KR890005073A (en) | Substituted triazolinones | |
| KR950008488A (en) | N-azinyl-N '-(het) arylsulfonyl-urea | |
| DK30883D0 (en) | ETHER DERIVATIVES OF SUBSTITUTED 1-HYDROXYALKYL-AZOLES, PROCEDURES FOR THEIR PREPARATION AND THEIR USE AS FUNGICIDES AND PLANT GROWTH REGULATORS | |
| BG60335B2 (en) | N-phenylsulphonyl-n'_triazinyl carbamides | |
| KR890017238A (en) | Sulfonylaminocarbonyltriazolinones | |
| RU2003105472A (en) | HERBICIDAL PRODUCT | |
| RU95120099A (en) | DERIVATIVES 3- (HET) ARYL-CARBIC ACID, METHOD AND INTERMEDIATE PRODUCTS FOR THEIR PRODUCTION | |
| RU2002107436A (en) | Herbicidal composition | |
| RU98121313A (en) | SUBSTITUTED AMINOMETHYLPHENYL SULPHONYLMOLAINS, THEIR RECEIVING AND USING AS HERBICIDES AND PLANT GROWTH REGULATORS | |
| RU96112194A (en) | DERIVATIVES OF PYRAZOLES AND CONTAINING THEIR HERBICIDES | |
| KR950700263A (en) | Herbicid N-[(1,3,5-Triazin-2-yl) aminocarbonyl] Benzenesulfonamides | |
| KR950000652A (en) | 2-oximino-2-phenyl-acetamide | |
| DE69119135D1 (en) | Substituted pyridine sulfonamide compounds, herbicidal compositions containing them and process for their preparation | |
| KR930002309A (en) | Salts of pyridylsulfonylurea as herbicides and plant growth regulators, preparation methods and uses thereof | |
| RU97103323A (en) | DERIVATIVES OF PYRAZINE WITH HERBICIDAL ACTIVITY | |
| KR930017890A (en) | N-heteroaryl-N '-(pyrid-2-yl-sulfonyl) urea, preparation method thereof, and use thereof as a herbicide and plant growth regulator | |
| RU99118300A (en) | PHENYLSULFONILMOCHEVINY, METHODS FOR THEIR PRODUCTION AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS | |
| AU619864B2 (en) | Substituted 4-sulphonylamino-2-azinyl-1,2,4-traizol-3-ones, processes and intermediates for their preparation and their use as herbicides |