6-(2-aminophenyl)picolinates and their use as herbicidesThe present invention relates to novel, herbicidally active 6-(2 -aminophenyl)picoline derivatives and processes for preparing them. The present invention further relates to the use thereof as herbicide, in particular as herbicide for the selective control of weeds in crop cultures, and as plant growth regulator either alone or in combination with safeners and/or in a mixture with other herbicides.The derivative that is fit to of the 6-of formula (i) (2-aminophenyl) pyridine carboxylic acid and n-oxide compound, salt, ester and agrochemistrywherein group is defined as follows separately:n is selected from 0,1,2,3,4 integer;r 1be selected from hydrogen, halogen, cyano group, nitro, amino, hydroxyl, (c 1-c 6) alkyl, (c 1-c 6) haloalkyl, (c 1-c 4) hydroxyalkyl, (c 2-c 6) alkoxyalkyl, (c 2-c 6) halogenated alkoxy alkyl, (c 2-c 6) thiazolinyl, (c 2-c 6) haloalkenyl group, (c 2-c 6) alkynyl, (c 3-c 6) halo alkynyl, (c 1-c 6) alkoxyl group, (c 1-c 6) halogenated alkoxy, (c 2-c 6) alkene oxygen base, (c 2-c 6) haloalkene oxygen base, (c 2-c 6) alkynyloxy group, (c 3-c 6) halo alkynyloxy group, (c 1-c 6) alkylthio, (c 2-c 6) alkylthio alkyl, (c 1-c 6) halogenated alkylthio, (c 1-c 6) alkyl sulphinyl, (c 1-c 6) haloalkyl sulfinyl, (c 1-c 6) alkyl sulphonyl, (c 1-c 6) halogenated alkyl sulfonyl, (c 2-c 6) alkenylthio group, (c 2-c 6) haloalkene sulfenyl, (c 2-c 6) thiazolinyl sulfinyl, (c 2-c 6) haloalkenyl group sulfinyl, (c 2-c 6) thiazolinyl alkylsulfonyl, (c 2-c 6) haloalkenyl group alkylsulfonyl, (c 2-c 6) alkynes sulfenyl, (c 3-c 6) acetylenic halide sulfenyl, (c 3-c 6) alkynyl sulfinyl, (c 3-c 6) halo alkynyl sulfinyl, (c 3-c 6) alkynyl alkylsulfonyl, (c 3-c 6) halo alkynyl alkylsulfonyl, (c 1-c 6) alkylamino, (c 2-c 6) dialkyl amido, (c 2-c 6) alkylamino alkyl, (c 2-c 6) alkyl-carbonyl, (c 2-c 6) alkoxy carbonyl, (c 2-c 6) aminocarboxyl, (c 2-c 6) alkyl amino-carbonyl, (c 3-c 8) dialkyl amino carbonyl, (c 3-c 6) trialkylsilkl, phenyl, phenoxy group and 5 yuan of hetero-aromatic rings or 6 yuan of hetero-aromatic rings, wherein each phenyl ring, benzene oxygen ring or 5 yuan of hetero-aromatic rings or 6 yuan of hetero-aromatic rings randomly can be by 1-3 r 25group replaces; perhaps two adjacent r wherein 1group can form-och together 2o-,-ch 2ch 2o-,-och 2ch 2o-,-och (ch 3) o-,-oc (ch 3) 2o-,-ocf 2o-,-cf 2cf 2o-,-ocf 2cf 2o-or-the ch=ch-ch=ch-group; r 2for hydrogen, halogen, cyano group, nitro, (c 1-c 6) alkyl, (c 1-c 6) haloalkyl, (c 1-c 6) alkoxyl group, (c 1-c 6) alkylamino, (c 1-c 6) dialkyl amido, (c 1-c 6) thio alkoxy, (c 2-c 6) thiazolinyl, (c 2-c 6) haloalkenyl group, (c 2-c 6) alkynyl; r 3for hydrogen, randomly by 1 or 2 r 6(the c that group replaces 1-c 4) alkyl, randomly by 1-2 r 7(the c that group replaces 2-c 4) thiazolinyl or randomly by 1 or 2 r 8(the c that group replaces 2-c 4) alkynyl; perhaps r 3for c (=o) r 9, no 2, or 10, s (o) 2r 11, n (r 12) r 13or n=c (r 14) r 15r 4for hydrogen, randomly by 1 or 2 r 6(the c that group replaces 1-c 4) alkyl or c (=o) r 9perhaps r 3and r 4formation-(ch together 2) 4-,-(ch 2) 5-,-ch 2ch=chch 2-or-(ch 2) 2o (ch 2) 2-group, described group are randomly by 1 or 2 r 16group replaces; perhaps r 3and r 4formation=c (r together 17) n (r 18) r 19or=c (r 20) or 21group; each r wherein 6, r 7and r 8group is independently selected from halogen, (c 1-c 3) alkoxyl group, (c 1-c 3) halogenated alkoxy, (c 1-c 3) alkylthio, (c 1-c 3) halogenated alkylthio, amino, (c 1-c 3) alkylamino, (c 2-c 4) dialkyl amido and (c 2-c 4) alkoxy carbonyl; r 5for hydrogen, halogen, cyano group, nitro, formyl radical, (c 1-c 6) alkyl, (c 2-c 6) thiazolinyl, (c 2-c 6) alkynyl, (c 1-c 6) haloalkyl, (c 2-c 6) haloalkenyl group, (c 1-c 6) alkoxyl group, (c 1-c 6) thio alkoxy, (c 2-c 6) alkoxyalkyl, (c 2-c 6) the thio alkoxy alkyl; r 9for hydrogen, (c 1-c 4) alkyl, (c 1-c 4) haloalkyl, (c 1-c 4) alkoxyl group, phenyl, phenoxy group, benzyl or benzyloxy; r 10for hydrogen, (c 1-c 4) alkyl, (c 1-c 3) haloalkyl or chr 22c (o) or 23r 11for (c 1-c 4) alkyl, (c 1-c 4) haloalkyl or randomly by 1,2 or 3, be independently selected from ch 3, cl and och 3the phenyl that replaces of group; r 12for hydrogen, (c 1-c 4) alkyl or c (=o) r 24r 13for hydrogen or (c 1-c 4) alkyl; r 14for hydrogen, (c 1-c 4) alkyl or randomly by 1,2 or 3, be independently selected from ch 3, cl or och 3the phenyl that replaces of group; r 15for hydrogen or (c 1-c 4) alkyl; or r 14and r 15formation-(ch together 2) 4-or-(ch 2) 5-group; r 16be halogen, (c independently 1-c 3) alkyl, (c 1-c 3) alkoxyl group, (c 1-c 3) halogenated alkoxy, (c 1-c 3) alkylthio, (c 1-c 3) halogenated alkylthio, amino, (c 1-c 3) alkylamino, (c 2-c 4) dialkyl amido or (c 2-c 4) alkoxy carbonyl; r 17for hydrogen or (c 1-c 4) alkyl; r 18and r 19be selected from independently of one another hydrogen and (c 1-c 4) alkyl; or r 18and r 19formation-(ch together 2) 4-,-(ch 2) 5-,-ch 2ch=chch 2-or-(ch 2) 2o (ch 2) 2-group; r 20for hydrogen or (c 1-c 4) alkyl; r 21for (c 1-c 4) alkyl; r 22for hydrogen, (c 1-c 4) alkyl, (c 1-c 3) haloalkyl, (c 1-c 4) alkoxyl group, phenyl, phenoxy group or benzyloxy; r 23for hydrogen, (c 1-c 4) alkyl or (c 1-c 4) alkoxyl group; r 24for hydrogen, c 1-c 4alkyl or benzyl; and r 25randomly be independent of other r 25be selected from halogen, cyano group, nitro, (c group 1-c 6) alkyl, (c 1-c 6) haloalkyl, (c 2-c 4) thiazolinyl, (...
6-(2-아미노페닐)피콜리네이트 및 제초제로서의 그의 용도 본 발명은 신규 제초 활성 6-(2-아미노페닐)피콜린 유도체 및 그의 제조방법에 관한 것이다. 본 발명은 또한 단독으로 또는 약해완화제와 병용으로 및/또는 다른 제초제와의 혼합물로서 제초제, 특히 유용한 작물에서 잡초 식물을 선택적으로 방제하기 위한 제초제 및 식물 성장 조절제로서의 그의 용도에 관한 것이다.화학식 (I)의 6-(2-아미노페닐)피콜리네이트, 및 그의 N-옥사이드, 염, 에스테르 및 농약상 적합한 유도체:[이미지]상기 식에서, 래디칼들은 각각 다음과 같이 정의된다:n은 0, 1, 2, 3, 4 중에서 선택되는 정수이고;R1은 수소, 할로겐, 시아노, 니트로, 아미노, 하이드록실, (C1-C6)알킬, (C1-C6)할로알킬, (C1-C4)하이드록시알킬, (C2-C6)알콕시알킬, (C2-C6)할로알콕시알킬, (C2-C6)알케닐, (C2-C6)할로알케닐, (C2-C6)알키닐, (C3-C6)할로알키닐, (C1-C6)알콕시, (C1-C6)할로알콕시, (C2-C6)알케닐옥시, (C2-C6)할로알케닐옥시, (C2-C6)알키닐옥시, (C3-C6)할로알키닐옥시, (C1-C6)알킬티오, (C2-C6)알킬티오알킬, (C1-C6)할로알킬티오, (C1-C6)알킬설피닐, (C1-C6)할로알킬설피닐, (C1-C6)알킬설포닐, (C1-C6)할로알킬설포닐, (C2-C6)알케닐티오, (C2-C6)할로알케닐티오, (C2-C6)알케닐설피닐, (C2-C6)할로알케닐설피닐, (C2-C6)알케닐설포닐, (C2-C6)할로알케닐설포닐, (C2-C6)알키닐티오, (C3-C6)할로알키닐티오, (C3-C6)알키닐설피닐, (C3-C6)할로알키닐설피닐, (C3-C6)알키닐설포닐, (C3-C6)할로알키닐설포닐, (C1-C6)알킬아미노, (C2-C6)디알킬아미노, (C2-C6)알킬아미노알킬, (C2-C6)알킬카보닐, (C2-C6)알콕시카보닐, (C2-C6)아미노카보닐, (C2-C6)알킬아미노카보닐, (C3-C8)디알킬아미노카보닐, (C3-C6)트리알킬실릴, 페닐, 페녹시 및 5- 또는 6-원 헤테로방향족 환으로 구성된 군에서 선택되고, 여기에서 각 페닐 환, 페녹시 환 또는 5- 또는 6-원 헤테로방향족 환은 1-3개의 R25 래디칼에 의해 임의로 치환될 수 있거나; 또는 두 인접 R1 래디칼은 함께, -OCH2O-, -CH2CH2O-, -OCH2CH2O-, -OCH(CH3)O-, -OC(CH3)2O-, -OCF2O-, -CF2CF2O-, -OCF2CF2O- 또는 -CH=CH-CH=CH- 그룹을 형성할 수 있고;R2는 수소, 할로겐, 시아노, 니트로, (C1-C6)알킬, (C1-C6)할로알킬, (C1-C6)알콕시, (C1-C6)알킬아미노, (C1-C6)디알킬아미노, (C1-C6)티오알콕시, (C2-C6)알케닐, (C2-C6)할로알케닐, (C2-C6)알키닐이고;R3은 수소, 1 또는 2개의 R6 래디칼에 의해 임의로 치환된 (C1-C4)알킬, 1-2개의 R7 래디칼에 의해 임의로 치환된 (C2-C4)알케닐, 또는 1 또는 2개의 R8 래디칼에 의해 임의로 치환된 (C2-C4)알키닐이거나; R3은 C(=O)R9, NO2, OR10, S(O)2R11, N(R12)R13 또는N=C(R14)R15이고;R4는 수소, 1 또는 2개의 R6 래디칼에 의해 임의로 치환된 (C1-C4)알킬, 또는 C(=O)R9이거나; 또는R3 및 R4는 함께, 1 또는 2개의 R16 래디칼에 의해 임의로 치환된 -(CH2)4-, -(CH2)5-, -CH2CH=CHCH2- 또는 -(CH2)2O(CH2)2- 그룹을 형성하거나; R3 및 R4는 함께, =C(R17)N(R18)R19 또는=C(R20)OR21 그룹을 형성하고;여기에서 각 R6, R7 및R8 래디칼은 독립적으로 할로겐, (C1-C3)알콕시, (C1-C3)할로알콕시, (C1-C3)알킬티오, (C1-C3)할로알킬티오, 아미노, (C1-C3)알킬아미노, (C2-C4)디알킬아미노 및 (C2-C4)알콕시카보닐중에서 선택되고; R5는 수소, 할로겐, 시아노, 니트로, 포르밀, (C1-C6)알킬, (C2-C6)알케닐, (C2-C6)알키닐, (C1-C6)할로알킬, (C2-C6)할로알케닐, (C1-C6)알콕시, (C1-C6)티오알콕시, (C2-C6)알콕시알킬, (C2-C6)티오알콕시알킬이고;R9는 수소, (C1-C4)알킬, (C1-C4)할로알킬, (C1-C4)알콕시, 페닐, 페녹시, 벤질 또는 벤질옥시이고; R10은 수소, (C1-C4)알킬, (C1-C3)할로알킬 또는 CHR22C(O)OR23이고;R11은 (C1-C4)알킬, (C1-C4)할로알킬 또는 CH3, Cl 및 OCH3 중에서 독립적으로 선택되는 1, 2 또는 3개의 래디칼에 의해 임의로 치환된 페닐이고;R12는 수소, (C1-C4)알킬 또는 C(=O)R24이고;R13은 수소 또는 (C1-C4)알킬이고;R14는 수소, (C1-C4)알킬 또는 CH3, Cl 또는 OCH3 중에서 독립적으로 선택되는 1, 2 또는 3개의 래디칼에 의해 임의로 치환된 페닐이고;R15는 수소 또는 (C1-C4)알킬이거나; 또는 R14 및 R15는 함께, -(CH2)4- 또는 -(CH2)5- 그룹을 형성하고;R16은 독립적으로 할로겐, (C1-C3)알킬, (C1-C3)알콕시, (C1-C3)할로알콕시, (C1-C3)알킬티오, (C1-C3)할로알킬티오, 아미노, (C1-C3)알킬아미노, (C2-C4)디알킬아미노 또는 (C2-C4)알콕시카보닐이고; R17은 수소 또는 (C1-C4)알킬이고;R18 및 R19는 각각 독립적으로 수소 및 (C1-C4)알킬중에서 선택되거나; 또는 R18 및 R19는 함께, -(CH2)4-, -(CH2)5-, -CH2CH=CHCH2- 또는 -(CH2)2O(CH2)2- 그룹을 형성하고; R20은 수소 또는 (C1-C4)알킬이고;R21은 (C1-C4)알킬이고; R22는 수소, (C1-C4)알킬, (C1-C3)할로알킬, (C1-C4)알콕시, 페닐, 페녹시 또는 벤질옥시이고; R23은 수소, (C1-C4)알킬 또는 (C1-C4)알콕시이고; R24는 수소, C1-C4 알킬 또는 벤질이고;R25는, 임의로 추가의 R25 래디칼과 독립적으로 할로겐, 시아노, 니트로, (C1-C6)알킬, (C1-C6)할로알킬, (C2-C4)알케닐, (C2-C4)할로알케닐, (C3-C4)알키닐, (C3-C4)할로알키닐, (C1-C4)알콕시, (C1-C4)할로알콕시, (C1-C4)알킬티오, (C1-C4)할로알킬티오, (C1-C4)알킬설피닐, (C1-C4)알킬설포닐, (C1-C4)알킬아미노, (C2-C8)디알킬아미노, (C2-C4)알킬카보닐, (C2-C6)알콕시카보닐, (C2-C6)알킬아미노카보닐, (C3-C8)디알킬아미노카보닐 및 (C3-C6)트리알킬실릴중에서 선택된다.